PEARL COTTAGE ~ Pristine Paradise!

PEARL COTTAGE ~ Renovated 3 Bedroom, 3 Bathroom Home with Heated Pool! Lush and Picturesque Gardens Abound!

Location

613 Margaret St. - FRONT
33040 Key West , FL
United States
24° 33' 26.658" N, 81° 47' 48.8112" W
See map: Google Maps
Florida US

PEARL COTTAGE ~ Pristine Paradise!

Request More Information

Time At Pearl Cottage

Reviewed by Nicole M. on 2023-10-04
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We had an absolutely incredible time at the Pearl Cottage! We love love love it! It is bright and light and decorated very nicely with high end beachy feel. It is spacious with 3 bedrooms and 4 baths! Nice pool and the location is absolutely perfect! Highly recommend! Service with Best of Key West Rentals is 5 star every time!
Manager response on 2023-10-04 - Response from Best of Key West Rentals
Thank you for taking the time to post a review of your stay at the Pearl Cottage Nicole. We are so happy to hear that you enjoyed your time in this beautiful home. Our goal is always to exceed your expectations! If there's anything we can help you with during your next visit, please don't hesitate to let us know. Thank you for being our guest!

5 Stars for Pearl Cottage

Reviewed by Unknown on 2024-03-16
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Pearl Cottage is a beautiful and comfortable home in an excellent location. We are a short walk from downtown, close to some excellent restaurants and on a quiet street.

The furniture and beds are comfortable and the pool is refreshing after our busy days. There is no indoor dining area and our manager has been helpful in dealing with a few minor issues.

I would highly recommend Pearl Cottage.
Manager response on 2024-03-18 - Response from Best of Key West Rentals
Thank you for this wonderful review Karen, we are so glad you enjoyed the property so much and hope to welcome you again next time you are in Key West.

cute cottage

Reviewed by Kevin A. on 2025-02-01
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This is a very cute cottage, and website photos were accurate in that regard. I would caution potential renters of the following:
There is NO garbage disposal, and you must constantly remove and clean a small screen covering the kitchen sink drain. The kitchen sink is very old, very deep, and along with the painted wooden countertops....need replaced / updated. 2) The skylights in the bedrooms with no shades, make it impossible to darken those rooms during daylight hours...they do provide great lighting for the rooms though. The master shower is large, the other two bedroom showers are plastic insert type showers, and are very tight for an adult.
Manager response on 2025-02-05 - Response from Best of Key West Rentals
Kevin thank you so much for taking the time to review your stay with us! we have sent your suggestions to the owners for consideration. We appreciate you choosing Best of key West Rentals for you tropical get away and hope to welcome you again next time you visit paradise!

A Beautiful Home

Reviewed by Unknown on 2025-04-01
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We enjoyed our stay in the Pearl Cottage. It is in a great location, a quiet neighborhood but close to the fun on Duval and at the harbour. The pool is excellent and we loved sitting on the front porch for our coffee. Our manager, Dan, was responsive to any questions or issues we had during our stay.
Manager response on 2025-04-02 - Response from Best of Key West Rentals
We are so happy you found this property and its location ideal for your get away in Key West Karen. We hope you'll stay with us again next time you visit!

Charming and great location - April 2025

Reviewed by Richard G. on 2025-05-07
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The cottage location and front porch are both terrific. Additionally the property management co. did a great job handling small issues. A real pleasure to work with. Would say however the marketing photos and description could have been more helpful when it came to the back patio and pool area which is separated from the back house on the property by a tall white fence. The fence blocks the airflow resulting in a very warm space. Additionally the shrubbery around and above the fence created quite of bit of debris which needed to be cleaned daily from the patio and pool. Finally the wifi did not work properly throughout our stay going out at least once an hour. Again we loved the location and our time on the beautiful front porch.
Manager response on 2025-05-07 - Response from Best of Key West Rentals
Thank you so much for your thoughtful review! We're thrilled to hear you enjoyed the cottage's fantastic location and the charm of the front porch—it’s one of our favorite features, too. We’re also glad our team was able to assist you promptly and that you found working with us a pleasure. We truly appreciate your feedback regarding the back patio and pool area. We understand how important clear and accurate descriptions are when choosing a property, and we’ll take a closer look at our listing to ensure it better reflects the layout and conditions, including airflow and landscaping impact. Your input helps us improve, and we hope to welcome you back to Key West soon—perhaps in a property that better fits your preferences. Thank you again for staying with us!

PEARL COTTAGE ~ 3 Bedroom, 3.5 Bathroom Home with Pool!

Unit Code: PE

PEARL COTTAGE ~ Pristine Paradise!

PEARL COTTAGE ~ Renovated 3 Bedroom, 3 Bathroom Home with Heated Pool! Lush and Picturesque Gardens Abound!
CONCH STYLE CHARM... This is the front cottage of the delightful Jewel Box Cottage compound, located in Old Town, just a stone's throw away from the magic of Duval Street and the historic Seaport. Abundant tropical foliage embraces the wrap-around front porch, inviting you to sit and people watch with your favorite beverage in hand. Wood floors and painted white walls line the space of this 1279 sq. ft. home that features vaulted ceilings and wooden beams and loads of Key West sunshine spills through multiple skylights. ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS AND AMENITIES… Sophisticated island style greets you as you enter the home which features a beautiful, modern kitchen, complete with island, stainless appliances and everything you'll need to cook for friends and family. The adjacent living/ area offers plush seating with a couch (also a sleeper sofa), loveseat and cushioned chair and smart TV for your viewing pleasure. A stacked washer and dryer occupy the half bath which is located just off the living area. This home is equipped with Roku TV. This home has a mounted outdoor camera but is NOT in use during guest stays. SLEEPING ARRANGEMENTS… There are 3 bedrooms, two with queen beds and one with a king bed. All bedrooms come with private en suite bathrooms with showers, ample storage space and two of the rooms include a TV. OUTDOOR LIVING… Enjoy your covered porch with a beautiful heated pool and outdoor dining for 6 as well as loungers for lazy afternoons. Lose yourself on the stunning pathways that lead you through gorgeous lush gardens and grounds. PETS... Dogs are permitted and a pet fee is required. Please leave the size and breed in the comments when inquiring or booking. MULTI MONTH RESERVATIONS... For monthly reservations, the following fees will be added PER MONTH: Mid-stay clean Pool/hot tub heating fee (if applicable) Pet fee (if applicable) PARKING... This home does not come with parking therefore guests must locate parking on the street in the surrounding neighborhood. BOOKING DATES... This home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. CONCIERGE SERVICES... Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival! CANCELLATION... Bookings canceled at least 90 days before the start of stay will receive a 100% refund. Cancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s). PICTURESQUE RETREAT…
December 2025
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
January 2026
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
February 2026
SuMoTuWeThFrSa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
Age 18 and under.
DatesPrice
12/15/2025 - 12/31/2025$286 /nt
01/01/2026 - 01/31/2026$750 /nt
02/01/2026 - 02/28/2026$844 /nt
03/01/2026 - 03/31/2026$713 /nt
04/01/2026 - 04/30/2026$572 /nt
05/01/2026 - 07/31/2026$429 /nt
08/01/2026 - 08/31/2026$411 /nt
09/01/2026 - 09/30/2026$429 /nt
10/01/2026 - 10/31/2026$447 /nt
11/01/2026 - 11/30/2026$465 /nt
12/01/2026 - 12/15/2026$536 /nt
4.7500
(8 Review)

Charming and great location - April 2025

April 2025
, Telluride, CO United States

Overall
4
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
3

The cottage location and front porch are both terrific. Additionally the property management co. did a great job handling small issues. A real pleasure to work with. Would say however the marketing photos and description could have been more helpful when it came to the back patio and pool area which is separated from the back house on the property by a tall white fence. The fence blocks the airflow resulting in a very warm space. Additionally the shrubbery around and above the fence created quite of bit of debris which needed to be cleaned daily from the patio and pool. Finally the wifi did not work properly throughout our stay going out at least once an hour. Again we loved the location and our time on the beautiful front porch.

Manager's Response

Thank you so much for your thoughtful review! We're thrilled to hear you enjoyed the cottage's fantastic location and the charm of the front porch—it’s one of our favorite features, too. We’re also glad our team was able to assist you promptly and that you found working with us a pleasure.

We truly appreciate your feedback regarding the back patio and pool area. We understand how important clear and accurate descriptions are when choosing a property, and we’ll take a closer look at our listing to ensure it better reflects the layout and conditions, including airflow and landscaping impact.

Your input helps us improve, and we hope to welcome you back to Key West soon—perhaps in a property that better fits your preferences. Thank you again for staying with us!

A Beautiful Home

March 2025
, Huntsville, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We enjoyed our stay in the Pearl Cottage. It is in a great location, a quiet neighborhood but close to the fun on Duval and at the harbour. The pool is excellent and we loved sitting on the front porch for our coffee. Our manager, Dan, was responsive to any questions or issues we had during our stay.

Manager's Response

We are so happy you found this property and its location ideal for your get away in Key West Karen. We hope you'll stay with us again next time you visit!

cute cottage

January 2025
, Mandeville, LA US

Overall
4
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

This is a very cute cottage, and website photos were accurate in that regard. I would caution potential renters of the following:
There is NO garbage disposal, and you must constantly remove and clean a small screen covering the kitchen sink drain. The kitchen sink is very old, very deep, and along with the painted wooden countertops....need replaced / updated. 2) The skylights in the bedrooms with no shades, make it impossible to darken those rooms during daylight hours...they do provide great lighting for the rooms though. The master shower is large, the other two bedroom showers are plastic insert type showers, and are very tight for an adult.

Manager's Response

Kevin thank you so much for taking the time to review your stay with us! we have sent your suggestions to the owners for consideration. We appreciate you choosing Best of key West Rentals for you tropical get away and hope to welcome you again next time you visit paradise!

5 Stars for Pearl Cottage

February 2024
, Huntsville, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Pearl Cottage is a beautiful and comfortable home in an excellent location. We are a short walk from downtown, close to some excellent restaurants and on a quiet street.

The furniture and beds are comfortable and the pool is refreshing after our busy days. There is no indoor dining area and our manager has been helpful in dealing with a few minor issues.

I would highly recommend Pearl Cottage.

Manager's Response

Thank you for this wonderful review Karen, we are so glad you enjoyed the property so much and hope to welcome you again next time you are in Key West.

5 Stars for Pearl Cottage

February 2024
, Huntsville, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Pearl Cottage is a beautiful and comfortable home in an excellent location. We are a short walk from downtown, close to some excellent restaurants and on a quiet street.

The furniture and beds are comfortable and the pool is refreshing after our busy days. There is no indoor dining area and our manager has been helpful in dealing with a few minor issues.

I would highly recommend Pearl Cottage.

Manager's Response

Thank you for this wonderful review Karen, we are so glad you enjoyed the property so much and hope to welcome you again next time you are in Key West.

Time At Pearl Cottage

September 2023
, St Petersburg, FL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We had an absolutely incredible time at the Pearl Cottage! We love love love it! It is bright and light and decorated very nicely with high end beachy feel. It is spacious with 3 bedrooms and 4 baths! Nice pool and the location is absolutely perfect! Highly recommend! Service with Best of Key West Rentals is 5 star every time!

Manager's Response

Thank you for taking the time to post a review of your stay at the Pearl Cottage Nicole. We are so happy to hear that you enjoyed your time in this beautiful home. Our goal is always to exceed your expectations! If there's anything we can help you with during your next visit, please don't hesitate to let us know. Thank you for being our guest!

Time At Pearl Cottage

September 2023
, St Petersburg, FL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We had an absolutely incredible time at the Pearl Cottage! We love love love it! It is bright and light and decorated very nicely with high end beachy feel. It is spacious with 3 bedrooms and 4 baths! Nice pool and the location is absolutely perfect! Highly recommend! Service with Best of Key West Rentals is 5 star every time!

Manager's Response

Thank you for taking the time to post a review of your stay at the Pearl Cottage Nicole. We are so happy to hear that you enjoyed your time in this beautiful home. Our goal is always to exceed your expectations! If there's anything we can help you with during your next visit, please don't hesitate to let us know. Thank you for being our guest!

Time At Pearl Cottage

September 2023
, Saint Petersburg, FL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We had an absolutely incredible time at the Pearl Cottage! We love love love it! It is bright and light and decorated very nicely with high end beachy feel. It is spacious with 3 bedrooms and 4 baths! Nice pool and the location is absolutely perfect! Highly recommend! Service with Best of Key West Rentals is 5 star every time!

Manager's Response

Thank you for taking the time to post a review of your stay at the Pearl Cottage Nicole. We are so happy to hear that you enjoyed your time in this beautiful home. Our goal is always to exceed your expectations! If there's anything we can help you with during your next visit, please don't hesitate to let us know. Thank you for being our guest!

Leave a Review
3 Bed
3.5 Baths
Sleeps 8

Search Availability

FLAMINGO ROSE ~ Dreaming of Paradise!

FLAMINGO ROSE ~ Peaceful, Midtown Home w/ 3 Bedroom, 2 Bathroom, Heated Pool, Parking & Dog Friendly! Magnificent Backyard Oasis!

Location

1616 Rose St.
33040 Key West , FL
United States
24° 33' 6.2676" N, 81° 46' 52.0464" W
See map: Google Maps
Florida US

FLAMINGO ROSE ~ Dreaming of Paradise!

Request More Information

Enjoyed the House

Reviewed by Unknown on 2025-02-15
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We have rented numerous houses in the Florida Keys over a period of 15 years or so. For the price, location, and features this is a favorite. It has among the nicest of the backyards, I.e. the size, the pool and the Tiki hut. The house was clean and well kept. Had all the basic features and supplies one would want in a rental house. The only disappointment was in the size of the master bedroom bath; small and cramped, not what you would expect for a master bathroom. Noteworthy too is that the property management was very responsive, addressing any issues in a timely manner. Bottom line is that we have contracted for the house for the month of January 2026 and would not have done so if we were not completely satisfied with our experience in 2025.
Manager response on 2025-02-24 - Response from Best of Key West Rentals
Thank you for this wonderful review Raymond, we are so glad you enjoyed the property so much you are planning on coming back! We look forward to welcoming you again next time you are in Key West.

A Blissful stay at a beautiful location

Reviewed by Wendy and Matthew Z. on 2023-07-03
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This was a great property that comes with awesome amenities and a really wonderful property management company! The Property Manager Melanie did a wonderful job and great communication. She had tons of great ideas for things to do and ways for our children to enjoy! I would highly recommend this company and this property!
Manager response on 2023-12-06 - Response from Best of Key West Rentals
Thank you for your wonderful review Wendy. We are thrilled you loved this home and hope to host you again soon!

FLAMINGO ROSE ~ Midtown 3 Bedroom, 2 Bathroom Home w/ Pool & Parking!

Unit Code: FR

FLAMINGO ROSE ~ Dreaming of Paradise!

FLAMINGO ROSE ~ Peaceful, Midtown Home w/ 3 Bedroom, 2 Bathroom, Heated Pool, Parking & Dog Friendly! Magnificent Backyard Oasis!
ISLAND NIRVANA AWAITS… Imagine your perfect island oasis for indoor/outdoor entertaining and gathering with friends and family. You'll love the vibrant backyard hideaway for relaxation and pleasure under the Key West sunshine. This wonderful 3 bedroom/2 bath home is nestled in a quiet Midtown neighborhood, but is only a brief walk to the picturesque sandy beaches and all the fun the Southernmost City has to offer! ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS AND AMENITIES... Step inside to the bright and cheery open concept floor plan, showcasing terrazzo flooring throughout and casual coastal decor that will soothe your senses and mesmerize your island soul. The living area greets you first and invites you to stay a while. Sink down into cozy couches and indulge in your favorite shows on the giant smart tv. Ready to tackle some culinary creations? The adjoining kitchen is fully stocked and equipped for elaborate meals and adult concoctions, with modern stainless appliances, granite counters, a kitchen island that seats 2, and a dining table for 6. There is an office located off the kitchen and is a perfect space when you need to plug in with work remotely. A full bath with a glass door shower is next to the office for your convenience. SLEEPING ARRANGEMENTS... The primary bedroom offers a plush king bed and ensuite bathroom with a glass door shower. Abundant natural light spills in from French doors that lead to the backyard area. A hanging/storage closet and clothing dresser will accommodate all of your vacation belongings. A TV provides enjoyment while you sink down into crisp bedding. There is another cozy king bedroom that offers a clothing dresser and a tv. The last bedroom has twin beds, a TV and a clothing dresser for storage. A queen sofa sleeper lies in the living area for visiting guests. OUTDOOR LIVING... The magnificent backyard is the centerpiece of this delightful island abode and will provide hours of enjoyment and relaxation. Lush tropical foliage surrounds a spacious heated pool with beautiful decking and a festive Chickee hut with a wrap-around bar, kitchenette, TV, hammock, outdoor shower, gas grill and ample cushioned loungers and chairs throughout the playful space. There is ample seating around the bar as well as an outdoor table so you can dine under the sultry stars! PARKING... There is off street parking available for this home. PETS... This is a dog friendly home only and a pet fee is required. BOOKING DATES... This home is offered only as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. CANCELLATION... Bookings canceled at least 90 days before the start of stay will receive a 100% refund. Cancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s). CONCIERGE SERVICES... Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival! YOUR ISLAND ZEN IS HERE…
December 2025
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
January 2026
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
February 2026
SuMoTuWeThFrSa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
Age 18 and under.
DatesPrice
12/15/2025 - 12/31/2025$420 /nt
01/01/2026 - 01/31/2026$358 /nt
02/01/2026 - 02/28/2026$713 /nt
03/01/2026 - 03/31/2026$645 /nt
04/01/2026 - 04/30/2026$393 /nt
05/01/2026 - 07/31/2026$304 /nt
08/01/2026 - 09/30/2026$250 /nt
10/01/2026 - 10/31/2026$358 /nt
11/01/2026 - 11/30/2026$375 /nt
12/01/2026 - 12/15/2026$465 /nt
5.0000
(4 Review)

Enjoyed the House

January 2025
, Crofton, MD Unknown

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We have rented numerous houses in the Florida Keys over a period of 15 years or so. For the price, location, and features this is a favorite. It has among the nicest of the backyards, I.e. the size, the pool and the Tiki hut. The house was clean and well kept. Had all the basic features and supplies one would want in a rental house. The only disappointment was in the size of the master bedroom bath; small and cramped, not what you would expect for a master bathroom. Noteworthy too is that the property management was very responsive, addressing any issues in a timely manner. Bottom line is that we have contracted for the house for the month of January 2026 and would not have done so if we were not completely satisfied with our experience in 2025.

Manager's Response

Thank you for this wonderful review Raymond, we are so glad you enjoyed the property so much you are planning on coming back! We look forward to welcoming you again next time you are in Key West.

A Blissful stay at a beautiful location

June 2023
, United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This was a great property that comes with awesome amenities and a really wonderful property management company! The Property Manager Melanie did a wonderful job and great communication. She had tons of great ideas for things to do and ways for our children to enjoy! I would highly recommend this company and this property!

A Blissful stay at a beautiful location

June 2023
, United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This was a great property that comes with awesome amenities and a really wonderful property management company! The Property Manager Melanie did a wonderful job and great communication. She had tons of great ideas for things to do and ways for our children to enjoy! I would highly recommend this company and this property!

Manager's Response

Thank you for your wonderful review Wendy. We are thrilled you loved this home and hope to host you again soon!

A Blissful stay at a beautiful location

June 2023
, KEY WEST, FL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This was a great property that comes with awesome amenities and a really wonderful property management company! The Property Manager Melanie did a wonderful job and great communication. She had tons of great ideas for things to do and ways for our children to enjoy! I would highly recommend this company and this property!

Manager's Response

Thank you for your wonderful review Wendy. We are thrilled you loved this home and hope to host you again soon!

Leave a Review
3 Bed
2 Baths
Sleeps 8

Search Availability

A SALTWATER REMEDY ~ Tranquility!

A SALTWATER REMEDY ~ Updated 2 BR/2.5 Ba Townhome Located in the Exclusive Porter Court of Truman Annex w/quiet Shared Pool!

Location

407 Porter Court
33040 Key West , FL
United States
24° 33' 16.668" N, 81° 48' 20.772" W
See map: Google Maps
Florida US

A SALTWATER REMEDY ~ Tranquility!

Request More Information

Excellent property

Reviewed by Unknown on 2025-04-01
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This is a wonderful property in a wonderful location. The property management team led by Whitney is exceptional.
Manager response on 2025-04-02 - Response from Best of Key West Rentals
Thank you for this great review Brian! We are thrilled you enjoyed the property and hope to host you again in the future!

Winter in KW

Reviewed by Unknown on 2025-03-01
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
When we arrived we discovered that the white cushions on the couch on the deck were filthy- stained and mildewed- too disgusting to touch, let alone- sit on. Whitney removed them the next day and replaced them with her own cushions, which didn't fit properly, but we were able to use the deck. The proper cushions were never replaced.
Manager response on 2025-03-19 - Response from Best of Key West Rentals
Anne thank you for writing this review. We are aware of the issue and have shared it with the owner. Please reach out to us next time you plan a vacation in Key West, we will make sure you have a 5 star stay.

Wonderful experience

Reviewed by Unknown on 2024-03-30
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The property was in excellent condition, very clean and well appointed. Most of the Porter Court residents are owners and they were very welcoming. Whitney, the property manager, was incredible. We are definitely returning in the future.
Manager response on 2024-03-30 - Response from Best of Key West Rentals
Brian we are thrilled you enjoyed your stay on Porter Court so much! We look forward to welcoming your next time you plan to spend time in paradise!

Perfect in Every Way!

Reviewed by Eileen O. on 2024-03-15
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Our month long stay at Saltwater REmedy was absolutely perfect! It is a lovely condo, kitchen is well equipped, quiet neighborhood, and a convenient location. The owner was very responsive and the Property Manager, Whitney, was outstanding! Before we left, we asked to book it for February of 2025 but it was already booked!
Manager response on 2024-03-15 - Response from Best of Key West Rentals
Eileen thank you so much for this fantastic review, we are so glad you enjoyed A Saltwater Remedy so much you wished to come back next year. We would be happy to offer you a selection of equally beautiful homes available February 2025, please contact us when you get a chance. Thank you for being our guest!

Truely tranquil

Reviewed by Unknown on 2024-02-06
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Relaxing
Manager response on 2024-03-15 - Response from Best of Key West Rentals
Thank you for this short and sweet review Anne, we really enjoyed hosting you and hope to welcome you again next time you visit our beautiful island!

A SALTWATER REMEDY~2 BR/2.5 Ba Truman Annex/Porter Court Townhome/Shared Pool

Unit Code: AS

A SALTWATER REMEDY ~ Tranquility!

A SALTWATER REMEDY ~ Updated 2 BR/2.5 Ba Townhome Located in the Exclusive Porter Court of Truman Annex w/quiet Shared Pool!
PERFECT CAREFREE RETREAT... Located in the small private community of Porter Court within Truman Annex and set around a graceful pool and hot tub. This is a smaller community within the gated Truman Annex community that provides a little extra privacy and peace and quiet. This delightful 2 bedroom 2.5 bath townhome is mere steps from all the excitement and beauty that is Key West. This highly coveted community is within walking distance of the famous Duval Street, Mallory Square, world-famous sunsets and countless restaurants and galleries. This prime location places you close to all the fun and attractions but is a quiet and peaceful refuge for your island bliss. ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS AND AMENITIES... Enter through the front gate where you are greeted by a cozy porch that entices you to sit and enjoy cool island breezes while you plan your island adventures. Enter through the front door to the open kitchen and living areas that have been lovingly updated and maintained. Fashion your foodie favorites in the fully-equipped kitchen which includes an electric stove, microwave, large French door refrigerator, coffee maker, toaster oven, and kitchen breakfast bar area (seats 2). The cabinets house every tool and appliance you will need to whip up scrumptious meals. Gather around the dining table for 6, then settle down on the plush sectional couch (also converts to sleeper sofa) and enjoy your favorite programs on the large wall-mounted TV. A powder room is located in the living area. SLEEPING ARRANGEMENTS... Travel up the stairs to two en-suite guest rooms when you're ready to rest and refresh for the next day's adventures. The first bedroom features two twin beds that can convert to a king upon request, a desk/work area, large double closets, a smart TV and large windows that allow plenty of cheerful sunshine inside. The bathroom offers a shower/tub combination. The second bedroom also features a king bed, double closets with built-in storage, smart TV, and a charming balcony with seating for two that has a view of the community pool and gardens. The en suite bathroom offers a tiled rain shower. A laundry closet is located upstairs and features a full-size stacked washer and dryer. OUTDOOR LIVING... French doors open to a lovely private deck area with deluxe outdoor furnishings and lush foliage. Fire up the grill and dine al fresco under the sultry tropical stars. Swimming in the heated community pool and spa is a great way to wash off the day and it's just steps from the home. There is a cabana with restrooms in the pool area and ample lounging chairs for your sunbathing pleasure. PARKING.... This home does offer parking for one vehicle, but oversized trucks and extra large SUVs are not permitted and will have to park outside of this community. The maximum length of the vehicle is 18 feet. PETS... This is not a pet-friendly home. MULTI MONTH RESERVATIONS... For monthly reservations, the following fees will be added PER MONTH: Mid-stay clean Pool/hot tub heating fee (if applicable) Pet fee (if applicable) CONCIERGE SERVICES... Enjoy our concierge service to assist you with planning activities for your trip. They can also have your fridge stocked with all the necessities in advance of your arrival! BOOKING DATES... This home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. CANCELLATION... Bookings canceled at least 90 days before the start of stay will receive a 100% refund. Cancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).
December 2025
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
January 2026
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
February 2026
SuMoTuWeThFrSa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
Age 18 and under.
DatesPrice
12/15/2025 - 12/31/2025$411 /nt
01/01/2026 - 01/31/2026$600 /nt
02/01/2026 - 02/28/2026$713 /nt
03/01/2026 - 03/31/2026$645 /nt
04/01/2026 - 04/30/2026$465 /nt
05/01/2026 - 09/30/2026$250 /nt
10/01/2026 - 10/31/2026$286 /nt
11/01/2026 - 11/30/2026$304 /nt
12/01/2026 - 12/15/2026$465 /nt
5.0000
(5 Review)

Excellent property

March 2025
, East Amherst, NY United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This is a wonderful property in a wonderful location. The property management team led by Whitney is exceptional.

Manager's Response

Thank you for this great review Brian! We are thrilled you enjoyed the property and hope to host you again in the future!

Wonderful experience

March 2024
, East Amherst, NY United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The property was in excellent condition, very clean and well appointed. Most of the Porter Court residents are owners and they were very welcoming. Whitney, the property manager, was incredible. We are definitely returning in the future.

Manager's Response

Brian we are thrilled you enjoyed your stay on Porter Court so much! We look forward to welcoming your next time you plan to spend time in paradise!

Wonderful experience

March 2024
, East Amherst, NY United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The property was in excellent condition, very clean and well appointed. Most of the Porter Court residents are owners and they were very welcoming. Whitney, the property manager, was incredible. We are definitely returning in the future.

Manager's Response

Brian we are thrilled you enjoyed your stay on Porter Court so much! We look forward to welcoming your next time you plan to spend time in paradise!

Perfect in Every Way!

January 2024
, New Hope, PA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Our month long stay at Saltwater REmedy was absolutely perfect! It is a lovely condo, kitchen is well equipped, quiet neighborhood, and a convenient location. The owner was very responsive and the Property Manager, Whitney, was outstanding! Before we left, we asked to book it for February of 2025 but it was already booked!

Manager's Response

Eileen thank you so much for this fantastic review, we are so glad you enjoyed A Saltwater Remedy so much you wished to come back next year. We would be happy to offer you a selection of equally beautiful homes available February 2025, please contact us when you get a chance. Thank you for being our guest!

Truely tranquil

January 2024
, Columbus, OH United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Relaxing

Manager's Response

Thank you for this short and sweet review Anne, we really enjoyed hosting you and hope to welcome you again next time you visit our beautiful island!

Leave a Review
2 Bed
2.5 Baths
Sleeps 6

Search Availability

BEACHY KEEN ~ Quaint Delight!

BEACHY KEEN ~ 1 Bedroom, 1 Bath Historic and Charming Cottage w/ Upstairs Sleeping Loft in Fantastic Key West Location!

Location

1010 whitehead
33040 key west , FL
United States
24° 32' 59.964" N, 81° 48' 0.864" W
See map: Google Maps
Florida US

BEACHY KEEN ~ Quaint Delight!

Request More Information

Great rental property

Reviewed by Unknown on 2025-03-02
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The property was great. And the rental folks amazing.
Manager response on 2025-08-04 - Response from Best of Key West Rentals
Your kind words mean the world to us Susan! Hosting you was an honor, and we can’t wait for the chance to welcome you back to our little slice of paradise.

The best little beach house in Key West!

Reviewed by Vincent D. on 2024-08-13
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The Beachy Keen rental was exactly as described and the pictures accurate. The location was quiet and quaint but still close to all the action. The home was spotless and perfect for my wife and I. The rental staff were professional and friendly and check in/out was easy and smooth. All the amenities you need are provided. We hope to stay here again soon.
Manager response on 2024-08-14 - Response from Best of Key West Rentals
Thank you for your fantastic review Vincent. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

Just Wonderful

Reviewed by Helen C. on 2024-04-01
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We absolutely loved our cottage. It was spotless and in a good location.
Manager response on 2024-04-11 - Response from Best of Key West Rentals
Thank you for this great review Helen! We are thrilled you enjoyed the property and hope to host you again in the future!

KW vacation 2024

Reviewed by Unknown on 2024-03-01
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This house is absolutely perfect. Location is everything. The front porch is amazing if you love to people watch. The house is completely stocked with everything you need. Hope to come back next year.
Manager response on 2024-03-01 - Response from Best of Key West Rentals
Thank you for this great review Andrea! We are thrilled you enjoyed the property and hope to host you again in the future!

A mixed Review

Reviewed by Unknown on 2024-02-15
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Positive.... except they rented it for next year to another person without letting us know. we had no idea that we had to reserve for the next year right after we moved in. that wasn't fair.
Manager response on 2024-02-15 - Response from Best of Key West Rentals
Judith we are glad you enjoyed the property so much you wanted to rent it for next year. We sent an email that explained you have the first week of your stay to commit to the following year. We had not heard back from you, so we contacted you directly about whether you would like the home before allowing others to book. You asked about weekly rentals and after sending you a selection to choose from, we waited to hear back from you. Once the deadline passed, a reservation came in for Beachy Keen . We are sorry you felt you didn't have enough time to make a decision but we tried to help. Please contact us if you have not found an alternative, we still have many beautiful homes available for next year. We'd love to welcome you again!

Kw2023

Reviewed by Donald P. on 2024-01-15
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Really enjoyed our stay at Beachy Keen. The location was convenient for walking to all restaurants, shops and attractions in the Old Town neighborhoods. Beachy Keen itself was clean and cozy and pet friendly.
We were always able to find non-resident street parking within a couple blocks of the cottage.
Manager response on 2024-01-16 - Response from Best of Key West Rentals
Thank you for your fantastic review Donald. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

A delightful stay

Reviewed by Unknown on 2023-11-17
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Beachy Keen is perfectly located to enjoy downtown Key West without being too noisy.

The house was recently remodeled and is in fantastic shape. Everything was as-described and it was very clean.

The highlight of our stay was probably our property manager, Dan. He was super responsive and helpful. He was a better host than most owners on AirBnb or VRBO are.

We already booked our next stay in 2024.

Manager response on 2023-11-17 - Response from Best of Key West Rentals
Thank you for your incredible review David! We are so thrilled to hear how much you loved this Key West retreat ! Dan and the entire team at Best of Key West Rentals are looking forward to hosting you again next year. Thank you for being our guest!

BEACHY KEEN ~ Charming 1 BR, 1 Ba Home w/ Loft in Great Location!

Unit Code: BK

BEACHY KEEN ~ Quaint Delight!

BEACHY KEEN ~ 1 Bedroom, 1 Bath Historic and Charming Cottage w/ Upstairs Sleeping Loft in Fantastic Key West Location!
CLASSIC KEY WEST CHARMER... Welcome to this historic one bedroom one bath abode that features an additional sleeping loft for guests! This quaint delight is just a short stroll from world-class restaurants, famous bars, shopping, museums and historical points of interest, such as the Lighthouse and Hemingway House. This is an ideal location for living your authentic island life, close to all the exciting action yet tucked into a quiet and colorful neighborhood. ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS AND AMENITIES… Walk through your private white picket gate and enter this adorable cottage that features a bright and updated living room and kitchen area. Tropical sunshine is abundant through large windows and vaulted ceilings that give this charmer a spacious feel. Cool off and relax on the couch and cushioned chair while you enjoy your movies on the wall-mounted TV. The living area opens to the spacious and modern dine-in kitchen. Sharpen your creative culinary skills in this fully equipped kitchen that offers stainless appliances and stone countertops. The bathroom is adjacent to the kitchen and has been fully renovated. Wash your cares away in the walk-in glass door rain shower. A stacked washer and dryer occupy the bathroom closet for your convenience. SLEEPING ARRANGEMENTS… The queen bedroom will invite you to rest and recharge after your day in paradise. Snuggle up with your favorite book or enjoy your wall-mounted tv in the plush bedding that promises sweet slumber. Unpack your shorts and sandals in the hanging/storage closet and clothing dresser. There is also a loft that is accessed by a wall ladder. It offers an additional queen bed for guests. OUTDOOR LIVING… The darling front porch is a wonderful spot for morning coffee and quiet reflection. A very private backyard patio can be accessed through the French doors in the kitchen, a perfect space for grilling up your fresh catch, rinsing off in the outdoor shower and an intimate conversation while star gazing. PARKING... This home does not have designated parking but there is on street parking in the surrounding neighborhood.  Please refrain from parking in spots marked “residential”. Guests may also park at the Old Town Parking Garage which allows daily and monthly rates. PETS... This home allows for pets under 35 lb and a pet fee is required. Please either inquire prior to booking, or make sure to check the box that you are bringing a pet when booking, AND include size, breed, and age of the pet in Comments/Special Requests. MULTI MONTH RESERVATIONS... For monthly reservations, the following fees will be added PER MONTH: Mid-stay clean Pool/hot tub heating fee (if applicable) Pet fee (if applicable) BOOKING DATES... This home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. CONCIERGE SERVICES... Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival! CANCELLATION... Bookings canceled at least 90 days before the start of stay will receive a 100% refund. Cancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s). AUTHENTIC ISLAND LIVING…
December 2025
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
January 2026
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
February 2026
SuMoTuWeThFrSa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
Age 18 and under.
DatesPrice
12/15/2025 - 12/31/2025$109 /nt
01/01/2026 - 01/31/2026$304 /nt
02/01/2026 - 02/28/2026$338 /nt
03/01/2026 - 03/31/2026$250 /nt
04/01/2026 - 04/30/2026$233 /nt
05/01/2026 - 07/31/2026$188 /nt
08/01/2026 - 09/30/2026$150 /nt
10/01/2026 - 10/31/2026$179 /nt
11/01/2026 - 11/30/2026$197 /nt
12/01/2026 - 12/15/2026$215 /nt
4.6667
(9 Review)

Great rental property

February 2025
, Annapolis, MD United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The property was great. And the rental folks amazing.

Manager's Response

Your kind words mean the world to us Susan! Hosting you was an honor, and we can’t wait for the chance to welcome you back to our little slice of paradise.

The best little beach house in Key West!

June 2024
, Bowersville, GA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The Beachy Keen rental was exactly as described and the pictures accurate. The location was quiet and quaint but still close to all the action. The home was spotless and perfect for my wife and I. The rental staff were professional and friendly and check in/out was easy and smooth. All the amenities you need are provided. We hope to stay here again soon.

Manager's Response

Thank you for your fantastic review Vincent. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

Just Wonderful

March 2024
, Weymouth, MA US

Overall
5
Services from rental manager
4
Cleanliness
5
Location
5
Property condition
5

We absolutely loved our cottage. It was spotless and in a good location.

Manager's Response

Thank you for this great review Helen! We are thrilled you enjoyed the property and hope to host you again in the future!

KW vacation 2024

February 2024
, Princeville, IL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This house is absolutely perfect. Location is everything. The front porch is amazing if you love to people watch. The house is completely stocked with everything you need. Hope to come back next year.

Manager's Response

Thank you for this great review Andrea! We are thrilled you enjoyed the property and hope to host you again in the future!

A mixed Review

January 2024
, WABAN, MA United States

Overall
4
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
3

Positive.... except they rented it for next year to another person without letting us know. we had no idea that we had to reserve for the next year right after we moved in. that wasn't fair.

Manager's Response

Judith we are glad you enjoyed the property so much you wanted to rent it for next year. We sent an email that explained you have the first week of your stay to commit to the following year.

We had not heard back from you, so we contacted you directly about whether you would like the home before allowing others to book. You asked about weekly rentals and after sending you a selection to choose from, we waited to hear back from you. Once the deadline passed, a reservation came in for Beachy Keen . We are sorry you felt you didn't have enough time to make a decision but we tried to help. Please contact us if you have not found an alternative, we still have many beautiful homes available for next year. We'd love to welcome you again!

A mixed Review

January 2024
, Waban, MA United States

Overall
4
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
3

Positive.... except they rented it for next year to another person without letting us know. we had no idea that we had to reserve for the next year right after we moved in. that wasn't fair.

Manager's Response

Judith we are glad you enjoyed the property so much you wanted to rent it for next year. We sent an email that explained you have the first week of your stay to commit to the following year.

We had not heard back from you, so we contacted you directly about whether you would like the home before allowing others to book. You asked about weekly rentals and after sending you a selection to choose from, we waited to hear back from you. Once the deadline passed, a reservation came in for Beachy Keen . We are sorry you felt you didn't have enough time to make a decision but we tried to help. Please contact us if you have not found an alternative, we still have many beautiful homes available for next year. We'd love to welcome you again!

A mixed Review

January 2024
, Waban, MA United States

Overall
4
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
3

Positive.... except they rented it for next year to another person without letting us know. we had no idea that we had to reserve for the next year right after we moved in. that wasn't fair.

Manager's Response

Judith we are glad you enjoyed the property so much you wanted to rent it for next year. We sent an email that explained you have the first week of your stay to commit to the following year.

We had not heard back from you, so we contacted you directly about whether you would like the home before allowing others to book. You asked about weekly rentals and after sending you a selection to choose from, we waited to hear back from you. Once the deadline passed, a reservation came in for Beachy Keen . We are sorry you felt you didn't have enough time to make a decision but we tried to help. Please contact us if you have not found an alternative, we still have many beautiful homes available for next year. We'd love to welcome you again!

Kw2023

December 2023
, Navarre, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Really enjoyed our stay at Beachy Keen. The location was convenient for walking to all restaurants, shops and attractions in the Old Town neighborhoods. Beachy Keen itself was clean and cozy and pet friendly.
We were always able to find non-resident street parking within a couple blocks of the cottage.

Manager's Response

Thank you for your fantastic review Donald. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

A delightful stay

October 2023
, Pahrump, NV United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Beachy Keen is perfectly located to enjoy downtown Key West without being too noisy.

The house was recently remodeled and is in fantastic shape. Everything was as-described and it was very clean.

The highlight of our stay was probably our property manager, Dan. He was super responsive and helpful. He was a better host than most owners on AirBnb or VRBO are.

We already booked our next stay in 2024.

Manager's Response

Thank you for your incredible review David! We are so thrilled to hear how much you loved this Key West retreat ! Dan and the entire team at Best of Key West Rentals are looking forward to hosting you again next year. Thank you for being our guest!

Leave a Review
1 Bed
1 Bath
Sleeps 4

Search Availability

LA CASA ROSADA ~ Pretty in Pink!

LA CASA ROSADA ~ Adorable & Perfectly Located 2 BR, 2.5 Ba Bahama Village Home w/ Private Hot Tub and Steps to Everything!

Location

1103 Thomas
33040 Key West , FL
United States
24° 32' 55.428" N, 81° 48' 2.088" W
See map: Google Maps
Florida US

LA CASA ROSADA ~ Pretty in Pink!

Request More Information

Lovely spot

Reviewed by Unknown on 2024-11-17
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The house is nice, very clean, and in great condition in an excellent location.
Manager response on 2024-11-18 - Response from Best of Key West Rentals
Thank you for your wonderful review Lori. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!

Excellent Company with Beautiful Properties

Reviewed by Lisa R. on 2024-10-06
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Amazing Best company I have have ever rented from in 20yrs of traveling. Beautiful places with everything you need to enjoy your vacation. Just bring your swing suit and clothes!
Manager response on 2024-10-07 - Response from Best of Key West Rentals
Thank you for your fantastic review Lisa. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

LA CASA ROSADA ~ Perfectly Located 2 BR, 2.5 Ba Home w/ Private Hot Tub!

Unit Code: LR

LA CASA ROSADA ~ Pretty in Pink!

LA CASA ROSADA ~ Adorable & Perfectly Located 2 BR, 2.5 Ba Bahama Village Home w/ Private Hot Tub and Steps to Everything!
YOUR ISLAND TREASURE AWAITS... This cozy 2 bedroom 2.5 bath island sanctuary is nestled in the charming area of Bahama Village, a community known for its colorful Bahamian-style architecture and panoramic water views from the 19th century Key West Lighthouse. Enjoy close proximity to many popular open-air restaurants serving island-inspired fare, coconut-laden cocktails and live music. This home provides every creature comfort you'll need and is a short distance from lively Duval Street and sun-drenched beaches. ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS AND AMENITIES... As you enter this adorable pink retreat, the cozy living area greets you and invites you to kick off your sandals and stay a while. A comfy sleeper couch and cushioned seating envelops you while you enjoy diversion on the large wall-mounted tv and cool off from your day's adventures in paradise. Continue down the hallway where you'll find a laundry closet and a powder room for your comfort and convenience, then enter the dine-in kitchen (table for 4) and enjoy meal prep in this clean and fully equipped and stocked kitchen. This property is equipped with a Ring Doorbell located next to the front door of the home. SLEEPING ARRANGEMENTS... Travel upstairs where you'll find two bedrooms, each with their own private shower bathroom. The primary features a king bed and the second bedroom offers a queen. Both are equipped with wall-mounted tvs and storage closets for your belongings. OUTDOOR LIVING... You will love the quaint side yard hangout that offers a private hot tub, sunbathing loungers, an outside shower and 4 bicycles. A small porch gives entry to the kitchen area. PETS... Pets are considered and a pet fee is required. Please leave the size and breed in the comments when inquiring. MULTI MONTH RESERVATIONS... For monthly reservations, the following fees will be added PER MONTH: Mid-stay clean Pool/hot tub heating fee (if applicable) Pet fee (if applicable) PARKING... Enjoy the convenience of an off street graveled parking space for 1 vehicle. BOOKING DATES... This home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. CONCIERGE SERVICES... Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival! CANCELLATION... Bookings canceled at least 90 days before the start of stay will receive a 100% refund. Cancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s). SUN-FILLED PLEASURES AWAIT YOU....
December 2025
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
January 2026
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
February 2026
SuMoTuWeThFrSa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
Age 18 and under.
DatesPrice
12/15/2025 - 12/31/2025$226 /nt
01/01/2026 - 01/31/2026$400 /nt
02/01/2026 - 02/28/2026$450 /nt
03/01/2026 - 03/31/2026$380 /nt
04/01/2026 - 04/30/2026$233 /nt
05/01/2026 - 07/31/2026$179 /nt
08/01/2026 - 09/30/2026$161 /nt
10/01/2026 - 10/31/2026$215 /nt
11/01/2026 - 11/30/2026$233 /nt
12/01/2026 - 12/15/2026$250 /nt
5.0000
(6 Review)

Lovely spot

November 2024
, Sugarloaf Key, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The house is nice, very clean, and in great condition in an excellent location.

Manager's Response

Thank you for your wonderful review Lori. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!

Excellent Company with Beautiful Properties

October 2024
, United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Amazing Best company I have have ever rented from in 20yrs of traveling. Beautiful places with everything you need to enjoy your vacation. Just bring your swing suit and clothes!

Manager's Response

Thank you for your fantastic review Lisa. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

Perfection!

February 2024

Overall
5

We already loved Key West but this home was so inviting, it made our stay so enjoyable! The location is perfect.The only time we got in the car was to get visitors from the airport! We were able to walk everywhere from Mallory to the Southernmost Point, to Ft Zach State Park and the entire waterfront area. The bikes made for some fun afternoons as well! The home was well equipped and very comfortable. Great workspace for remote work as well.The side garden area was fantastic for morning coffee, a read in the shade and cool evening hot tubs! The neighborhood pool is only 2 blocks away and was a great spot for a cooling off. We would absolutely love to stay here again.

Manager's Response

Thank you for your wonderful review Coleen. We really enjoyed hosting you and hope to see you back in Key West again soon!

Best Location!

May 2023
, New Jersey

Overall
5

The Pink House on Thomas Street is definitely worth the stay! It is centrally located from all major spots. 20 minute walk to Fort Zachary Beach and 5 minutes to Southernmost Point!The house itself is stylish and well maintained.The hot tub at the house was amazing after a long day of shopping and fun on Duval Street.The community pool is steps away from the house and there is great dining options right down the street. Next time my family is back in Key West, we will be staying at the Pink House!

Manager's Response

Thank you for your wonderful review Michael. It was a pleasure hosting you and we can't wait to welcome you again next time you visit paradise!

True Island Vibe

April 2023
, Pennsylvania

Overall
5

Loved staying at La Casa Rosada! It is in the perfect location, great neighborhood and super close to everything! The house is decorated so nicely and has every accommodation available!Bikes, hot tub, relaxing fire pit! Truly achieved that relaxing, island vibe that I was seeking!With two full main bathrooms, perfect place for two couples to share! Hot tub was amazing! We will definitely be heading back again soon!!

Manager's Response

Thank you for this wonderful review Courtney, we are so glad you enjoyed the property so much you are planning on coming back! We look forward to welcoming you again next time you are in Key West.

Close to the beach

March 2023
, Virginia

Overall
5

This house is the perfect getaway! The owners have provided everything you need to enjoy your time in Key West. We were able to drop off our luggage and quickly take off on the bikes and explore. The location is perfect as well. A quick bike ride to a local beach was almost a daily event. We would then return and relax in the private yard. The home itself has all the best amenities - with a true Key West vibe.It's all the extras that make this place special!We will be back!

Manager's Response

Thank you for your wonderful review Lillie. It was a pleasure hosting you and we look forward to welcoming you again next time you visit paradise!

Leave a Review
2 Bed
2.5 Baths
Sleeps 6

Search Availability

THE SWEET LIFE ~ Treat Yourself!

THE SWEET LIFE ~ Pet Friendly, Adorable and Perfectly Located 2 BR/1 Ba Condo Just Steps to Everything w/ Community Pool!

Location

204-2 Southard St.
33040 Key West , FL
United States
24° 33' 8.496" N, 81° 48' 17.2584" W
See map: Google Maps
Florida US

THE SWEET LIFE ~ Treat Yourself!

Request More Information

Awesome Retreat!

Reviewed by Carol M. on 2025-11-07
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Great location that felt like home away from home!
Manager response on 2025-11-12 - Response from Best of Key West Rentals
Carol, we’re so glad you had a great time with us, it was truly a pleasure having you! We’d be delighted to welcome you back the next time your travels bring you to paradise.

Just super in every way.

Reviewed by Louise C. on 2025-09-29
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
From booking, to staying, to memories made, just a wonderful property. A very pretty property..beautifully presented and spotlessly clean. The bed was so comfortable and lovely quality bedding. The Sweet Life provided everything we needed. We loved the location too... really quiet and peaceful with a well kept private terrace and great pool area but also within a few minutes walk to bars, restaurants and the park. We hired bikes and cycled to the beach too...
Best of Key West were always there to help if we had any questions. Will be back for sure X
Manager response on 2025-09-30 - Response from Best of Key West Rentals
Louise,your kind words mean the world to us! Hosting you was an honor, and we can’t wait for the chance to welcome you back to our little slice of paradise.

Liven it up at The Sweet Life

Reviewed by Kimberlee K. on 2025-03-15
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We spent the month of February in 2024 and 2025 in this location. We are booked for 2026 also. The location is perfect to get to anywhere in Key West on foot, there’s also a shuttle called the Duval Loop which will take you anywhere free on the island. The property is appointed with everything you need. The condo was very clean. Any questions we had the property manager was very attentive. We can’t wait to get back to Paradise in 2026.
Manager response on 2025-04-22 - Response from Best of Key West Rentals
Thank you so much for your kind words Kimberlee and for being such a loyal guest! We're thrilled to hear that you’ve enjoyed both of your February stays and already have 2026 on the calendar, that means the world to us. It’s great to know the location, amenities, and cleanliness met your expectations, and that our team was able to assist you when needed. We can’t wait to welcome you back to your slice of Paradise in 2026!

Very nice condo.

Reviewed by Matthew V. on 2025-02-13
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Very nice place, as described. Quiet, Very convenient location.
Manager response on 2025-04-22 - Response from Best of Key West Rentals
Matthew, thank you for your feedback! We’re so glad to hear you enjoyed the quiet atmosphere and convenient location. It’s great to know everything met your expectations. We hope to welcome you back again soon!

Our place was great! Near everything we wanted to see.

Reviewed by Linda C. on 2024-10-22
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Place was as shown on pictures, clean and great location.
Manager response on 2025-04-22 - Response from Best of Key West Rentals
Linda we are so glads you enjoyed the location of the condo so much. We hope to welcome you again soon!

Best Rental

Reviewed by Susan N. on 2024-09-05
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This is the best rental I've ever had! Just the right size for 2 sisters looking for a little getaway. Great location within walking distance of almost everything on the lower half of the island. The beds were comfy, the kitchen well-equipped, and a nice living area to watch movies in at the end of a busy, sunny day. Everything was nice and clean and in good order. The unit had a washer/dryer and beach towels and plenty of linens were furnished. We are looking forward to renting again in the future.
Manager response on 2025-04-22 - Response from Best of Key West Rentals
Wow! Susa, thank you so much for the glowing review! We're absolutely thrilled to hear this was the best rental you’ve ever had. It sounds like you and your sister made the most of your getaway, and we’re so glad the space, amenities, and location suited you perfectly. We truly appreciate your kind words and can’t wait to welcome you back for another stay in the future!

Last Vacation to Key West

Reviewed by Cecile F. on 2024-04-29
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We rented the Condo at Shipyard because of the walkability factor. It was cozy and sufficient for a 1 week stay. It was clean and nicely decorated. We came to Key West to purchase a house, which we did, so we are now on our way to becoming Freshwater Conch's. I texted with Melanie and communication with her was great. So nice! I did use the pool at Shipyard which was nice. This is a two bedroom with queen beds and one bath so great for a family for a relaxing vacay! Thanks Melanie... It will be great to meet you!
Manager response on 2024-07-18 - Response from Best of Key West Rentals
Thank you for your fantastic review Cecile. It was a pleasure hosting you and we look forward to sharing this beautiful island now that you were promoted to the local's club! Welcome Home!

March birthday trip

Reviewed by Christian C. on 2024-03-25
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The rental was very clean, organized, and had a fully equipped kitchen. The deck and porch are were very clean and well maintained. The pool is clean and close to the unit. The beach and park are just a short walk from the rental. The check out instructions were clear and easy to follow. Parking was close to the unit and all of the codes were given prior to arrival, which made it very easy. The host was easily accessible through a text and a quick response to each inquiry.
Manager response on 2024-07-18 - Response from Best of Key West Rentals
Thank you for this great review Christian! We are thrilled you enjoyed the property and hope to host you again in the future!

Wonderful Accomodations in a Prime Location

Reviewed by Thomas T. on 2024-03-14
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
What a wonderful experience we had here at The Sweet Life. This was our first stay at the Shipyard and certainly won't be our last. Thank you to our wonderful host, Melanie for all your help in making our stay so enjoyable.
Manager response on 2024-07-18 - Response from Best of Key West Rentals
Thank you for your fantastic review. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

Best Month In Paradise

Reviewed by Kimberlee K. on 2024-03-11
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Great location. Car not needed within walking distance to everything. Property was clean and appointed with things needed to make your stay comfortable. The property manager took care of any questions that we had.
Manager response on 2024-07-18 - Response from Best of Key West Rentals
Thank you for your review. We are so thrilled to hear how much you loved this home and hope to see you again!

Truman VRBO

Reviewed by Unknown on 2023-11-14
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Great location
Manager response on 2023-12-13 - Response from Best of Key West Rentals
We are so happy you found this property and its location ideal for your get away in Key West Denise. We hope you'll stay with us again next time you visit!

Excellent

Reviewed by Jim M. on 2023-07-18
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Location was 2 short blocks from Duval at Southard. Gated condo community with lush landscaping. Fenced deck and rear courtyard area. Shared front porch with settee. Inside, all the amenities of home. Melanie was wonderful. Love Marcella who caretakes the outside. Will absolutely stay here again.
Manager response on 2023-12-13 - Response from Best of Key West Rentals
Thank you for this wonderful review Jim, we are so glad you enjoyed the property so much you are planning on coming back! We look forward to welcoming you again next time you are in Key West.

THE SWEET LIFE ~ Charming First Floor 2 BR/1 Ba Condo w/ Community Pool!

Unit Code: SWE

THE SWEET LIFE ~ Treat Yourself!

THE SWEET LIFE ~ Pet Friendly, Adorable and Perfectly Located 2 BR/1 Ba Condo Just Steps to Everything w/ Community Pool!
CUTE CONDO IN STEPS FROM IT ALL… This 2 bedroom, 1 bath ground level flat is located in The Shipyard, a neighborhood of the coveted Truman Annex in the heart of Old Town Key West! You will be in walking distance from Fort Zachary’s gorgeous beach and picnic area, Duval Street, Mallory Square and more! Throw your cares to the wind as you unwind in this charming, tree-shrouded neighborhood with walking paths and lanes. This cozy downstairs unit has everything you'll need for your stay in paradise! ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS AND AMENITIES... Enter through the white picket fence and you are greeted by a lovely front porch with sitting area where you can sip coffee and plan your island adventures for the day. The flowing floor plan offers a spacious and lovely living and dining area that offer rest and relaxation after a day in the sultry sun and balmy breezes of the island. Whip up your favorite recipes in the fully equipped and stocked kitchen that overlooks the living area. A dining table for 4 sits next to the kitchen where you can enjoy cozy meals with your loved ones. A comfy couch, plush cushioned chairs and smart tv in the living area provide the perfect resting spot for bingeing on your latest shows and movies. A stacked laundry closet sits just off the living area for your convenience. Open the French Doors to your sweet backyard oasis. SLEEPING ARRANGEMENTS… The first queen bedroom is on the left as you enter the home. It offers a spacious hanging closet, smart tv, and a clothing dresser for your belongings. The primary bedroom also has a queen bed, smart tv, large hanging closet and clothing dresser, and is adjacent to the full bathroom, where you can wash off the day in the shower/tub combination. OUTDOOR LIVING… The Shipyard offers a beautiful community pool lined with lounge chairs perfect for soaking up the sun. Open the French door in the living area to the delightful private deck, a shaded retreat outfitted for unwinding and refreshment. PARKING... This home does offer parking for one vehicle (vehicle cannot exceed 18 ft), but oversized trucks and extra large SUVs are not permitted and will have to park outside of this community. PETS... This is a pet friendly home with a required pet fee. Please include the size and breed when inquiring. MULTI MONTH RESERVATIONS... For monthly reservations, the following fees will be added PER MONTH: Mid-stay clean Pet Fee (if applicable) BOOKING DATES... This home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. CANCELLATION... Bookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund. CONCIERGE SERVICES... Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival! YOUR SWEET RETREAT...
December 2025
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
January 2026
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
February 2026
SuMoTuWeThFrSa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
Age 18 and under.
DatesPrice
12/15/2025 - 12/15/2025$117 /nt
12/16/2025 - 12/16/2025$111 /nt
12/17/2025 - 12/17/2025$132 /nt
12/18/2025 - 12/18/2025$137 /nt
12/19/2025 - 12/19/2025$164 /nt
12/20/2025 - 12/20/2025$167 /nt
12/21/2025 - 12/21/2025$117 /nt
12/22/2025 - 12/22/2025$196 /nt
12/23/2025 - 12/23/2025$200 /nt
12/24/2025 - 12/24/2025$236 /nt
12/25/2025 - 12/25/2025$269 /nt
12/26/2025 - 12/26/2025$298 /nt
12/27/2025 - 12/27/2025$314 /nt
12/28/2025 - 12/28/2025$402 /nt
12/29/2025 - 12/29/2025$429 /nt
12/30/2025 - 12/30/2025$241 /nt
12/31/2025 - 12/31/2025$442 /nt
01/01/2026 - 01/31/2026$250 /nt
02/01/2026 - 02/28/2026$358 /nt
03/01/2026 - 03/31/2026$304 /nt
04/01/2026 - 04/30/2026$286 /nt
05/01/2026 - 07/31/2026$161 /nt
08/01/2026 - 08/01/2026$362 /nt
08/02/2026 - 08/02/2026$293 /nt
08/03/2026 - 08/03/2026$219 /nt
08/04/2026 - 08/04/2026$216 /nt
08/05/2026 - 08/05/2026$222 /nt
08/06/2026 - 08/06/2026$266 /nt
08/07/2026 - 08/07/2026$299 /nt
08/08/2026 - 08/08/2026$305 /nt
08/09/2026 - 08/09/2026$239 /nt
08/10/2026 - 08/10/2026$215 /nt
08/11/2026 - 08/11/2026$207 /nt
08/12/2026 - 08/12/2026$215 /nt
08/13/2026 - 08/13/2026$263 /nt
08/14/2026 - 08/14/2026$298 /nt
08/15/2026 - 08/15/2026$297 /nt
08/16/2026 - 08/16/2026$222 /nt
08/17/2026 - 08/17/2026$198 /nt
08/18/2026 - 08/18/2026$188 /nt
08/19/2026 - 08/19/2026$191 /nt
08/20/2026 - 08/20/2026$240 /nt
08/21/2026 - 08/22/2026$277 /nt
08/23/2026 - 08/23/2026$206 /nt
08/24/2026 - 08/24/2026$184 /nt
08/25/2026 - 08/25/2026$176 /nt
08/26/2026 - 08/26/2026$178 /nt
08/27/2026 - 08/27/2026$227 /nt
08/28/2026 - 08/28/2026$266 /nt
08/29/2026 - 08/29/2026$303 /nt
08/30/2026 - 08/30/2026$199 /nt
08/31/2026 - 08/31/2026$174 /nt
09/01/2026 - 09/01/2026$207 /nt
09/02/2026 - 09/02/2026$209 /nt
09/03/2026 - 09/03/2026$257 /nt
09/04/2026 - 09/04/2026$327 /nt
09/05/2026 - 09/05/2026$331 /nt
09/06/2026 - 09/06/2026$268 /nt
09/07/2026 - 09/07/2026$245 /nt
09/08/2026 - 09/08/2026$173 /nt
09/09/2026 - 09/09/2026$177 /nt
09/10/2026 - 09/10/2026$244 /nt
09/11/2026 - 09/11/2026$284 /nt
09/12/2026 - 09/12/2026$287 /nt
09/13/2026 - 09/13/2026$218 /nt
09/14/2026 - 09/14/2026$188 /nt
09/15/2026 - 09/15/2026$175 /nt
09/16/2026 - 09/16/2026$186 /nt
09/17/2026 - 09/17/2026$234 /nt
09/18/2026 - 09/18/2026$275 /nt
09/19/2026 - 09/19/2026$282 /nt
09/20/2026 - 09/20/2026$215 /nt
09/21/2026 - 09/21/2026$192 /nt
09/22/2026 - 09/22/2026$185 /nt
09/23/2026 - 09/23/2026$203 /nt
09/24/2026 - 09/24/2026$253 /nt
09/25/2026 - 09/25/2026$298 /nt
09/26/2026 - 09/26/2026$305 /nt
09/27/2026 - 09/27/2026$238 /nt
09/28/2026 - 09/28/2026$210 /nt
09/29/2026 - 09/29/2026$190 /nt
09/30/2026 - 09/30/2026$215 /nt
10/01/2026 - 10/01/2026$262 /nt
10/02/2026 - 10/02/2026$308 /nt
10/03/2026 - 10/03/2026$316 /nt
10/04/2026 - 10/04/2026$246 /nt
10/05/2026 - 10/05/2026$216 /nt
10/06/2026 - 10/06/2026$202 /nt
10/07/2026 - 10/07/2026$217 /nt
10/08/2026 - 10/08/2026$271 /nt
10/09/2026 - 10/09/2026$329 /nt
10/10/2026 - 10/10/2026$340 /nt
10/11/2026 - 10/11/2026$268 /nt
10/12/2026 - 10/12/2026$235 /nt
10/13/2026 - 10/13/2026$208 /nt
10/14/2026 - 10/14/2026$217 /nt
10/15/2026 - 10/15/2026$272 /nt
10/16/2026 - 10/16/2026$377 /nt
10/17/2026 - 10/17/2026$383 /nt
10/18/2026 - 10/18/2026$316 /nt
10/19/2026 - 10/19/2026$288 /nt
10/20/2026 - 10/20/2026$280 /nt
10/21/2026 - 10/21/2026$294 /nt
10/22/2026 - 10/22/2026$349 /nt
10/23/2026 - 10/23/2026$394 /nt
10/24/2026 - 10/24/2026$402 /nt
10/25/2026 - 10/25/2026$356 /nt
10/26/2026 - 10/26/2026$248 /nt
10/27/2026 - 10/27/2026$241 /nt
10/28/2026 - 10/28/2026$256 /nt
10/29/2026 - 10/29/2026$306 /nt
10/30/2026 - 10/30/2026$745 /nt
10/31/2026 - 10/31/2026$746 /nt
11/01/2026 - 11/01/2026$682 /nt
11/02/2026 - 11/02/2026$649 /nt
11/03/2026 - 11/03/2026$647 /nt
11/04/2026 - 11/04/2026$659 /nt
11/05/2026 - 11/05/2026$704 /nt
11/06/2026 - 11/06/2026$739 /nt
11/07/2026 - 11/07/2026$746 /nt
11/08/2026 - 11/08/2026$683 /nt
11/09/2026 - 11/09/2026$643 /nt
11/10/2026 - 11/10/2026$328 /nt
11/11/2026 - 11/11/2026$320 /nt
11/12/2026 - 11/12/2026$307 /nt
11/13/2026 - 11/13/2026$331 /nt
11/14/2026 - 11/14/2026$341 /nt
11/15/2026 - 11/15/2026$274 /nt
11/16/2026 - 11/16/2026$240 /nt
11/17/2026 - 11/17/2026$235 /nt
11/18/2026 - 11/18/2026$250 /nt
11/19/2026 - 11/19/2026$290 /nt
11/20/2026 - 11/20/2026$307 /nt
11/21/2026 - 11/21/2026$326 /nt
11/22/2026 - 11/22/2026$266 /nt
11/23/2026 - 11/23/2026$308 /nt
11/24/2026 - 11/24/2026$304 /nt
11/25/2026 - 11/25/2026$317 /nt
11/26/2026 - 11/26/2026$349 /nt
11/27/2026 - 11/27/2026$374 /nt
11/28/2026 - 11/28/2026$389 /nt
11/29/2026 - 11/29/2026$257 /nt
11/30/2026 - 11/30/2026$224 /nt
12/01/2026 - 12/01/2026$216 /nt
12/02/2026 - 12/02/2026$227 /nt
12/03/2026 - 12/03/2026$257 /nt
12/04/2026 - 12/04/2026$289 /nt
12/05/2026 - 12/05/2026$306 /nt
12/06/2026 - 12/06/2026$258 /nt
12/07/2026 - 12/07/2026$233 /nt
12/08/2026 - 12/08/2026$227 /nt
12/09/2026 - 12/09/2026$235 /nt
12/10/2026 - 12/10/2026$271 /nt
12/11/2026 - 12/11/2026$310 /nt
12/12/2026 - 12/12/2026$330 /nt
12/13/2026 - 12/14/2026$288 /nt
12/15/2026 - 12/15/2026$275 /nt
4.9167
(12 Review)

Awesome Retreat!

October 2025
, Cocoa, FL United States

Overall
5
Property condition
5
Location
5
Cleanliness
5
Services from rental manager
5

Great location that felt like home away from home!

Manager's Response

Carol, we’re so glad you had a great time with us, it was truly a pleasure having you! We’d be delighted to welcome you back the next time your travels bring you to paradise.

Just super in every way.

September 2025
, United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

From booking, to staying, to memories made, just a wonderful property. A very pretty property..beautifully presented and spotlessly clean. The bed was so comfortable and lovely quality bedding. The Sweet Life provided everything we needed. We loved the location too... really quiet and peaceful with a well kept private terrace and great pool area but also within a few minutes walk to bars, restaurants and the park. We hired bikes and cycled to the beach too...
Best of Key West were always there to help if we had any questions. Will be back for sure X

Manager's Response

Louise,your kind words mean the world to us! Hosting you was an honor, and we can’t wait for the chance to welcome you back to our little slice of paradise.

Liven it up at The Sweet Life

February 2025
, Newport, KY Unknown

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We spent the month of February in 2024 and 2025 in this location. We are booked for 2026 also. The location is perfect to get to anywhere in Key West on foot, there’s also a shuttle called the Duval Loop which will take you anywhere free on the island. The property is appointed with everything you need. The condo was very clean. Any questions we had the property manager was very attentive. We can’t wait to get back to Paradise in 2026.

Manager's Response

Thank you so much for your kind words Kimberlee and for being such a loyal guest! We're thrilled to hear that you’ve enjoyed both of your February stays and already have 2026 on the calendar, that means the world to us. It’s great to know the location, amenities, and cleanliness met your expectations, and that our team was able to assist you when needed. We can’t wait to welcome you back to your slice of Paradise in 2026!

Very nice condo.

November 2024
, Fitchburg, WI US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Very nice place, as described. Quiet, Very convenient location.

Manager's Response

Matthew, thank you for your feedback! We’re so glad to hear you enjoyed the quiet atmosphere and convenient location. It’s great to know everything met your expectations. We hope to welcome you back again soon!

Our place was great! Near everything we wanted to see.

October 2024
, Batavia, IL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Place was as shown on pictures, clean and great location.

Manager's Response

Linda we are so glads you enjoyed the location of the condo so much. We hope to welcome you again soon!

Best Rental

August 2024
, Chattanooga, TN US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This is the best rental I've ever had! Just the right size for 2 sisters looking for a little getaway. Great location within walking distance of almost everything on the lower half of the island. The beds were comfy, the kitchen well-equipped, and a nice living area to watch movies in at the end of a busy, sunny day. Everything was nice and clean and in good order. The unit had a washer/dryer and beach towels and plenty of linens were furnished. We are looking forward to renting again in the future.

Manager's Response

Wow! Susa, thank you so much for the glowing review! We're absolutely thrilled to hear this was the best rental you’ve ever had. It sounds like you and your sister made the most of your getaway, and we’re so glad the space, amenities, and location suited you perfectly. We truly appreciate your kind words and can’t wait to welcome you back for another stay in the future!

Last Vacation to Key West

April 2024
, Pompano Beach, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We rented the Condo at Shipyard because of the walkability factor. It was cozy and sufficient for a 1 week stay. It was clean and nicely decorated. We came to Key West to purchase a house, which we did, so we are now on our way to becoming Freshwater Conch's. I texted with Melanie and communication with her was great. So nice! I did use the pool at Shipyard which was nice. This is a two bedroom with queen beds and one bath so great for a family for a relaxing vacay! Thanks Melanie... It will be great to meet you!

Manager's Response

Thank you for your fantastic review Cecile. It was a pleasure hosting you and we look forward to sharing this beautiful island now that you were promoted to the local's club! Welcome Home!

March birthday trip

March 2024
, Moundsville, WV US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The rental was very clean, organized, and had a fully equipped kitchen. The deck and porch are were very clean and well maintained. The pool is clean and close to the unit. The beach and park are just a short walk from the rental. The check out instructions were clear and easy to follow. Parking was close to the unit and all of the codes were given prior to arrival, which made it very easy. The host was easily accessible through a text and a quick response to each inquiry.

Manager's Response

Thank you for this great review Christian! We are thrilled you enjoyed the property and hope to host you again in the future!

Wonderful Accomodations in a Prime Location

February 2024
, Algona, IA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

What a wonderful experience we had here at The Sweet Life. This was our first stay at the Shipyard and certainly won't be our last. Thank you to our wonderful host, Melanie for all your help in making our stay so enjoyable.

Manager's Response

Thank you for your fantastic review. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

Best Month In Paradise

February 2024
, Newport, KY Unknown

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Great location. Car not needed within walking distance to everything. Property was clean and appointed with things needed to make your stay comfortable. The property manager took care of any questions that we had.

Manager's Response

Thank you for your review. We are so thrilled to hear how much you loved this home and hope to see you again!

Truman VRBO

November 2023
, Vero, FL US

Overall
4
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
4

Great location

Manager's Response

We are so happy you found this property and its location ideal for your get away in Key West Denise. We hope you'll stay with us again next time you visit!

Excellent

July 2023
, Palm Bay, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

Location was 2 short blocks from Duval at Southard. Gated condo community with lush landscaping. Fenced deck and rear courtyard area. Shared front porch with settee. Inside, all the amenities of home. Melanie was wonderful. Love Marcella who caretakes the outside. Will absolutely stay here again.

Manager's Response

Thank you for this wonderful review Jim, we are so glad you enjoyed the property so much you are planning on coming back! We look forward to welcoming you again next time you are in Key West.

Leave a Review
2 Bed
1 Bath
Sleeps 4

Search Availability

ANCHORS AWAY ~ Blissful!

ANCHORS AWAY ~ Cheerful 1 Bedroom, 1 Bath with Private Hot Tub Condo in The Meadows!

Location

707 Florida St.
33040 Key West , FL
United States
24° 33' 35.01" N, 81° 47' 28.104" W
See map: Google Maps
Florida US

ANCHORS AWAY ~ Blissful!

Request More Information

Thank you

Reviewed by Angelae W. on 2024-05-18
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Very Nice place...Dan the property manager was awesome.
Manager response on 2024-05-20 - Response from Best of Key West Rentals
Thank you Michael for this short and sweet review, it was such a pleasure hosting you this year! We hope to welcome you again in Key West soon!

ANCHORS AWAY ~ Cheerful 1 BR, 1 Ba Condo with Private Hot Tub in The Meadows!

Unit Code: AA

ANCHORS AWAY ~ Blissful!

ANCHORS AWAY ~ Cheerful 1 Bedroom, 1 Bath with Private Hot Tub Condo in The Meadows!
CLASSIC AND COZY... Exhale your worries away as you approach this delightful condo, one of four that are situated inside the Mahogany House, surrounded by the shade of Spanish lime trees and classic balustrades that confirm you've finally arrived in Key West. Located on a quiet corner of The Meadows community, you are within biking and walking distance to all of Old Town as well as the Garrison Bight waterfront for exciting boating adventures. ***GUESTS MUST BE 25 YEARS OF AGE OR OLDER DETAILS AND AMENITIES… Enter through your private entrance into this open and inviting pied a terre. Sink down into the comfortable furnishings of the living area and enjoy your favorite movie on the large wall-mounted TV or fall asleep reading your favorite novel as the sultry sunshine warms you through the large French doors that lead to your backyard oasis. The living area opens to the spacious and well-appointed kitchen, equipped with butcher block counters, stainless appliances and all of the culinary tools you need to create a fabulous meal. A table for 4 in the spacious kitchen invites you and your loved ones to dine in cozy comfort. Wash the day off in the renovated bathroom with a double sink vanity and glass-door shower. A separate laundry room with built-in cabinetry offers additional storage space for your essentials. A separate 108 square foot cottage lies in the backyard for your al fresco enjoyment (it is not air-conditioned), and has a sofa. SLEEPING ARRANGEMENTS… The charming king bedroom will soothe your senses, inviting you to rest after your day of fun and frivolity. Two large windows allow abundant tropical sunshine to brighten your mood and wake you for another day in paradise. A large wall-mounted TV tempts you to nestle down in your plush bedding for bingeworthy tv viewing. A sofa sleeper resides in the living area so you can invite friends or family to join you. OUTDOOR LIVING… Carry your iced and crafted cocktail out to your private backyard hideaway with ample outdoor seating and lush landscaping. This outdoor gem comes complete with an outdoor fire table, hot tub and open-air shower. Let the swaying palms and cooling breezes carry you away from the real world. You'll want to stay a while at this small but mighty jewel! PARKING... This home does not have designated parking but there is on street parking in the surrounding neighborhood. Please refrain from parking in spots marked “residential”. Guests may also park at the Old Town Parking Garage which allows daily and monthly rates. PETS... Dogs are considered at 45 lb. or less and a maximum of 2 per the HOA of the property. A pet fee is required. Please make sure to check the box that you are bringing a pet when booking, and include size, breed, and age of the pet in Comments/Special Requests. MULTI MONTH RESERVATIONS... For monthly reservations, the following fees will be added PER MONTH: Mid-stay clean Pool/hot tub heating fee (if applicable) Pet fee (if applicable) BOOKING DATES... This home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. CONCIERGE SERVICES... Enjoy our concierge service to assist you with planning activities for your trip. They can also have your fridge stocked with all the necessities in advance of your arrival! CANCELLATION... Bookings canceled at least 90 days before the start of stay will receive a 100% refund. Cancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s). YOU DESERVE TO BE HERE...
December 2025
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
January 2026
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
February 2026
SuMoTuWeThFrSa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
Age 18 and under.
DatesPrice
12/15/2025 - 12/31/2025$170 /nt
01/01/2026 - 01/31/2026$215 /nt
02/01/2026 - 02/28/2026$226 /nt
03/01/2026 - 03/31/2026$204 /nt
04/01/2026 - 04/30/2026$179 /nt
05/01/2026 - 07/31/2026$136 /nt
08/01/2026 - 09/30/2026$125 /nt
10/01/2026 - 10/31/2026$136 /nt
11/01/2026 - 11/30/2026$179 /nt
12/01/2026 - 12/15/2026$188 /nt
5.0000
(3 Review)

Thank you

April 2024
, United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Very Nice place...Dan the property manager was awesome.

Manager's Response

Thank you Michael for this short and sweet review, it was such a pleasure hosting you this year! We hope to welcome you again in Key West soon!

Thank you

April 2024
, United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Very Nice place...Dan the property manager was awesome.

Manager's Response

Thank you Michael for this short and sweet review, it was such a pleasure hosting you this year! We hope to welcome you again in Key West soon!

Thank you

April 2024
, United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Very Nice place...Dan the property manager was awesome.

Manager's Response

Thank you Michael for this short and sweet review, it was such a pleasure hosting you this year! We hope to welcome you again in Key West soon!

Leave a Review
1 Bed
1 Bath
Sleeps 4

Search Availability

WALKING ON SUNSHINE ~ Feels Good!

WALKING ON SUNSHINE ~ Centrally Located 3 BR, 3 Ba Home w/ Private Heated Pool & Parking!

Location

1609 Flagler Ave.
33040 Key West , FL
United States
24° 33' 13.284" N, 81° 46' 56.8704" W
See map: Google Maps
Florida US

WALKING ON SUNSHINE ~ Feels Good!

Request More Information

Wonderful Rental

Reviewed by ron n. on 2025-05-16
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We had a wonderful time from the moment we arrived through the last day of our stay. The rental was bright, airy, spacious and very clean. For us the location was perfect. Away from the hustle and bustle of Duval, with just a short $10 Uber ride to and from. The twenty-somethings were more than fine with that.
The pool was exceptional, large enough to swim laps. We never had an "iguana pool issue" as the dog kept them at bay throughout. And our dog was constantly entertained by the geckos out front. Our property manager, Shana, was competent and most friendly. This is unquestionably a 5-star rental!!! My only criticism, albeit minor, is that the pool entrance did not have a railing. Needing a hip replacement rendered entry somewhat problematic.
Manager response on 2025-05-16 - Response from Best of Key West Rentals
Thank you so much for your wonderful review Ron! We're thrilled to hear that your stay was enjoyable from beginning to end. It’s great to know the home’s layout, cleanliness, and peaceful location worked perfectly for your group — and that the proximity to Duval Street offered the best of both worlds. We’re especially happy to hear your dog had such a great time, both as iguana-deterrent and gecko enthusiast! I’ll be sure to pass along your kind words to Shana — she’ll be delighted to hear she made a positive impression. Thank you also for your feedback regarding the pool entrance. We truly value suggestions like yours, and we’ll explore options to make access more comfortable for all guests moving forward. We’d love to welcome you back anytime, thank you for being our guest!

Gracious Key West Escape

Reviewed by Teresa R. on 2025-01-02
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Love the home and experience.

A few things were fixed while we were there.

Excellent parking and lovely decor.

Unfortunately the garden and pool lights never worked and impacted our overall outside experience.
Manager response on 2025-01-03 - Response from Best of Key West Rentals
Thank you for this great review Teresa! We are thrilled you enjoyed the property despite some of the outdoor lighting acting up. They are still under warranty so the manufacturer is replacing them, we really wish they would have been fast enough to complete the job during your stay. We hope to get a chance to host you again in the future! Thank you for being our guest!

Family trip to paradise

Reviewed by Nick O. on 2024-08-07
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
An exciting experience to live the key west lifestyle. The home exceeded our expectations... a great layout, including a pool that is larger than most. I was able to work in the home office on the 2nd floor while the family chilled out back, enjoyed mango's onsite, rode bikes around the island, and brought fish home from a deep sea adventure. Easy walking distance to grocery, breakfast, and a wonderful food truck. Overall, a clean, maintained property.
Manager response on 2024-08-08 - Response from Best of Key West Rentals
Thank you for your fantastic review Nick. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

Overall wonderful property!

Reviewed by David M. on 2024-03-06
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This is a beautiful overall property with a great property manager! The outdoor space is just as described-lush, private, beautiful lighting and pool with great grill, lounge chairs and eating area. There is a good bit of construction noise but there is a lot of construction in KW. Airplanes fly close by much of the day but we got to where we enjoyed that. The kitchen is well-appointed, bright and open with great extra appliances like Keurig, coffee maker, tea pot, blender. It has a beautiful décor and open floor plan. Added fun extras like bright beach towels, playing cards, candles, books, etc. make it very welcoming. On-site parking is a bonus but because this home is only 1/3 mile from Higgs Beach (sunrise, sunset, pickleball), a mile from Southernmost Point and 2 miles to Duvall waterfront, we only drove to pick up airport friends and groceries. Everywhere else we walked or rode bikes. It’s the BEST WAY to enjoy the wonderfully friendly, fun island.
The backyard is 5 stars! The property manager is 5 stars! The only reason we give 4 overall stars instead of 5 is because of a few issues (some rotten windows and front decking for example) that are not expected for this type of lovely property. All of the bedrooms face Flagler Ave, which is a busy street with constant lights at night so blackout curtains would greatly enhance stay.

We embraced the popular happy hours and did everything outside! Some of our faves: Two Friends, Salty Frog and Conch Republic. Santiago Bodega has wonderful food and service. Make a happy hour reservation. Antonia’s has an amazing dinner (sat at bar), Sloppy Joe’s is a must (go see our friend Larry of Sloppy Seconds). Make a reservation at Better Than Sex for dessert and Latitudes for brunch. Check out El Siboney for the Cuban, Blue Heaven for a Bacon Avocado Benedict, SaraBeth’s for Key Lime French Toast, and the sandwich stand or Brady's 2 blocks away. Check out the farmers markets on Sun & Th.
Manager response on 2024-03-07 - Response from Best of Key West Rentals
Thank you for your feedback on your recent stay David. We are so glad that you enjoyed your time spent at this home. We appreciate your feedback that we will rely back to the owners for consideration. Thank you again and please reach out to us for your next Key West vacation!

WALKING ON SUNSHINE ~ Exquisite 3 BR, 3 Ba Home w/ Heated Pool & Parking!

Unit Code: WA

WALKING ON SUNSHINE ~ Feels Good!

WALKING ON SUNSHINE ~ Centrally Located 3 BR, 3 Ba Home w/ Private Heated Pool & Parking!
A FEAST FOR THE EYES… This exquisite 3 bedroom, 3 bath abode will delight your artistic senses with its gorgeous interior and lush outside spaces. Owned by a renowned London-based designer, this worldly and sophisticated showpiece home displays amazing attention to detail and has been fully renovated and restored for your pleasure. This is a fantastic Midtown location, near the Casa Marina and Atlantic beaches and just a short distance to the island's attractions. ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS AND AMENITIES... This home features a beautifully designed interior that includes high ceilings, hardwood floors and an open floor plan. Step inside to the living area where East meets West with a whimsical modern flair. The large tv and beautiful furnishings invite you to relax and enjoy the artistry that surrounds you. A dining table for 6 inhabits the living area and there is also a kitchen bar with seating for 3. The immaculate kitchen is fully equipped with modern appliances and is stocked with everything you'll need. Sliding doors to the backyard oasis merge inside and outside spaces, giving you the authentic Key West living experience. Each bedroom has its own bathroom and there is a full-sized laundry room upstairs as well. SLEEPING ARRANGEMENTS... A queen bedroom resides downstairs that opens to the front porch. There is a TV and adjoining bathroom that offers a glass-door shower and has double entry doors to the pool area and downstairs. A storage closet is located in the bathroom. Travel upstairs to the other bedrooms. The primary suite offers a lovely office area that overlooks the backyard oasis. The king bedroom lulls you in with its promise of relaxation and the enjoyment of its unique design. A large tv and two closets ensure your comfort in this grand space. The bathroom features a shower/tub combination. The third bedroom houses two twin beds (can be converted to a king upon request), with a tv and small dresser. The third bathroom is adjacent to the twin bedroom and offers a shower/tub combination. OUTDOOR LIVING... There is a front porch as you enter the home and an upper balcony that looks out over the backyard and heated pool. Enjoy your morning coffee and views from these lovely spaces, then venture out to your sparkling pool with teak deck. Your outdoor refuge is surrounded by tropical foliage, al fresco seating for dining under the stars, lounge chairs for sunbathing and a gas grill. You and your loved ones will enjoy many hours in this backyard slice of heaven. PARKING... There is off street parking on the double driveway. PETS... Dogs under 35 lbs are considered and a pet fee is required. Please leave the size / breed in the comments when inquiring. MULTI MONTH RESERVATIONS... For monthly reservations, the following fees will be added PER MONTH: Mid-stay clean Pool/hot tub heating fee (if applicable) Pet fee (if applicable) BOOKING DATES... This home is offered only as a monthly rental (28 night min.). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. CANCELLATION... Bookings canceled at least 90 days before the start of stay will receive a 100% refund. Cancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s). CONCIERGE SERVICES... Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!
December 2025
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
January 2026
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
February 2026
SuMoTuWeThFrSa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
Age 18 and under.
DatesPrice
12/15/2025 - 12/31/2025$215 /nt
01/01/2026 - 01/31/2026$465 /nt
02/01/2026 - 02/28/2026$675 /nt
03/01/2026 - 03/31/2026$536 /nt
04/01/2026 - 04/30/2026$411 /nt
05/01/2026 - 07/31/2026$304 /nt
08/01/2026 - 09/30/2026$286 /nt
10/01/2026 - 10/31/2026$304 /nt
11/01/2026 - 11/30/2026$322 /nt
12/01/2026 - 12/15/2026$411 /nt
4.8333
(6 Review)

Wonderful Rental

April 2025
, augusta, ME US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We had a wonderful time from the moment we arrived through the last day of our stay. The rental was bright, airy, spacious and very clean. For us the location was perfect. Away from the hustle and bustle of Duval, with just a short $10 Uber ride to and from. The twenty-somethings were more than fine with that.
The pool was exceptional, large enough to swim laps. We never had an "iguana pool issue" as the dog kept them at bay throughout. And our dog was constantly entertained by the geckos out front. Our property manager, Shana, was competent and most friendly. This is unquestionably a 5-star rental!!! My only criticism, albeit minor, is that the pool entrance did not have a railing. Needing a hip replacement rendered entry somewhat problematic.

Manager's Response

Thank you so much for your wonderful review Ron! We're thrilled to hear that your stay was enjoyable from beginning to end. It’s great to know the home’s layout, cleanliness, and peaceful location worked perfectly for your group — and that the proximity to Duval Street offered the best of both worlds.

We’re especially happy to hear your dog had such a great time, both as iguana-deterrent and gecko enthusiast! I’ll be sure to pass along your kind words to Shana — she’ll be delighted to hear she made a positive impression.

Thank you also for your feedback regarding the pool entrance. We truly value suggestions like yours, and we’ll explore options to make access more comfortable for all guests moving forward.

We’d love to welcome you back anytime, thank you for being our guest!

Gracious Key West Escape

December 2024
, Alexandria, VA US

Overall
4
Services from rental manager
4
Cleanliness
5
Location
4
Property condition
4

Love the home and experience.

A few things were fixed while we were there.

Excellent parking and lovely decor.

Unfortunately the garden and pool lights never worked and impacted our overall outside experience.

Manager's Response

Thank you for this great review Teresa! We are thrilled you enjoyed the property despite some of the outdoor lighting acting up. They are still under warranty so the manufacturer is replacing them, we really wish they would have been fast enough to complete the job during your stay. We hope to get a chance to host you again in the future! Thank you for being our guest!

Family trip to paradise

July 2024
, RESTON, VA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
4
Property condition
5

An exciting experience to live the key west lifestyle. The home exceeded our expectations... a great layout, including a pool that is larger than most. I was able to work in the home office on the 2nd floor while the family chilled out back, enjoyed mango's onsite, rode bikes around the island, and brought fish home from a deep sea adventure. Easy walking distance to grocery, breakfast, and a wonderful food truck. Overall, a clean, maintained property.

Manager's Response

Thank you for your fantastic review Nick. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

Overall wonderful property!

February 2024
, Mount Pleasant , SC United States

Overall
5
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
4

This is a beautiful overall property with a great property manager! The outdoor space is just as described-lush, private, beautiful lighting and pool with great grill, lounge chairs and eating area. There is a good bit of construction noise but there is a lot of construction in KW. Airplanes fly close by much of the day but we got to where we enjoyed that. The kitchen is well-appointed, bright and open with great extra appliances like Keurig, coffee maker, tea pot, blender. It has a beautiful décor and open floor plan. Added fun extras like bright beach towels, playing cards, candles, books, etc. make it very welcoming. On-site parking is a bonus but because this home is only 1/3 mile from Higgs Beach (sunrise, sunset, pickleball), a mile from Southernmost Point and 2 miles to Duvall waterfront, we only drove to pick up airport friends and groceries. Everywhere else we walked or rode bikes. It’s the BEST WAY to enjoy the wonderfully friendly, fun island.
The backyard is 5 stars! The property manager is 5 stars! The only reason we give 4 overall stars instead of 5 is because of a few issues (some rotten windows and front decking for example) that are not expected for this type of lovely property. All of the bedrooms face Flagler Ave, which is a busy street with constant lights at night so blackout curtains would greatly enhance stay.

We embraced the popular happy hours and did everything outside! Some of our faves: Two Friends, Salty Frog and Conch Republic. Santiago Bodega has wonderful food and service. Make a happy hour reservation. Antonia’s has an amazing dinner (sat at bar), Sloppy Joe’s is a must (go see our friend Larry of Sloppy Seconds). Make a reservation at Better Than Sex for dessert and Latitudes for brunch. Check out El Siboney for the Cuban, Blue Heaven for a Bacon Avocado Benedict, SaraBeth’s for Key Lime French Toast, and the sandwich stand or Brady's 2 blocks away. Check out the farmers markets on Sun & Th.

Manager's Response

Thank you for your feedback on your recent stay David. We are so glad that you enjoyed your time spent at this home. We appreciate your feedback that we will rely back to the owners for consideration. Thank you again and please reach out to us for your next Key West vacation!

Overall wonderful property!

February 2024
, Mount Pleasant , SC United States

Overall
5
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
4

This is a beautiful overall property with a great property manager! The outdoor space is just as described-lush, private, beautiful lighting and pool with great grill, lounge chairs and eating area. There is a good bit of construction noise but there is a lot of construction in KW. Airplanes fly close by much of the day but we got to where we enjoyed that. The kitchen is well-appointed, bright and open with great extra appliances like Keurig, coffee maker, tea pot, blender. It has a beautiful décor and open floor plan. Added fun extras like bright beach towels, playing cards, candles, books, etc. make it very welcoming. On-site parking is a bonus but because this home is only 1/3 mile from Higgs Beach (sunrise, sunset, pickleball), a mile from Southernmost Point and 2 miles to Duvall waterfront, we only drove to pick up airport friends and groceries. Everywhere else we walked or rode bikes. It’s the BEST WAY to enjoy the wonderfully friendly, fun island.
The backyard is 5 stars! The property manager is 5 stars! The only reason we give 4 overall stars instead of 5 is because of a few issues (some rotten windows and front decking for example) that are not expected for this type of lovely property. All of the bedrooms face Flagler Ave, which is a busy street with constant lights at night so blackout curtains would greatly enhance stay.

We embraced the popular happy hours and did everything outside! Some of our faves: Two Friends, Salty Frog and Conch Republic. Santiago Bodega has wonderful food and service. Make a happy hour reservation. Antonia’s has an amazing dinner (sat at bar), Sloppy Joe’s is a must (go see our friend Larry of Sloppy Seconds). Make a reservation at Better Than Sex for dessert and Latitudes for brunch. Check out El Siboney for the Cuban, Blue Heaven for a Bacon Avocado Benedict, SaraBeth’s for Key Lime French Toast, and the sandwich stand or Brady's 2 blocks away. Check out the farmers markets on Sun & Th.

Manager's Response

Thank you for your feedback on your recent stay David. We are so glad that you enjoyed your time spent at this home. We appreciate your feedback that we will rely back to the owners for consideration. Thank you again and please reach out to us for your next Key West vacation!

Great House!

July 2023

Overall
5

I traveled with my parents and two children, the kids and I stayed the entire 4 weeks while my parents, husband and brother stopped in during the four weeks we were there. I work full time remote and the office set up was perfect. I could work during the day and still listen the kids playing in the pool. Being in Key West while working made it a great way to truly experience the key west culture and lifestyle. Each evening after work, we made sure to get out and about. The layout of the house was great as it felt like each room was separate from the other and that you had your own private space. The location was perfect for our family, since we had children with us, we didn’t want to be at the heart of Duval street, but we were still so close to everything- a short scooter ride away. The pool was one of the bigger ones I noticed and was perfect for the entire family, having a deeper end for jumping in. The iguanas were all over the place! Coming from Kentucky, this was a really cool thing to watch. The down side is they poop a lot on the deck, but every morning we would take the hose and wash it off. We did end up moving the chairs under the upper deck to keep the poop off them. We also travelled with dogs; the owner and property management company were really flexible with us on our request. My family and I loved our time here and I would highly recommend others take the time to live the key west life

Manager's Response

Sonya, we are so happy you found this property and its location ideal for your get away in Key West. We love to hear how you felt like a local, experiencing all the lifestyle and sharing it with your family. We hope you'll stay with us again next time you get a chance! Thank you for being our guest!

Leave a Review
3 Bed
3 Baths
Sleeps 6

Search Availability

BRIGHT SUNSHINY DAY ~ Dreamy!

BRIGHT SUNSHINY DAY ~ Upscale and Perfectly Located 3 Bedroom, 4 Bathroom Home w/ Pool, Spa and Exercise Room!

Location

1112 Southard St.
33040 Key West , FL
United States
24° 33' 33.5952" N, 81° 47' 40.6356" W
See map: Google Maps
Florida US

BRIGHT SUNSHINY DAY ~ Dreamy!

Request More Information

Beautiful Place

Reviewed by Nikolaus M. on 2025-11-24
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The house and property were excellent. Beautiful pool, great kitchen, and the location was PERFECT! We’d gladly stay here again if it’s available next year.
Manager response on 2025-11-28 - Response from Best of Key West Rentals
Thanks so much for the lovely feedback! We’re happy to hear you enjoyed the property and would love to host you again in the future.

Enjoyed Staying at Bright Sunshiny Day

Reviewed by Unknown on 2024-10-31
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This house is wonderful! It is spacious, clean and is in one the best neighborhoods in KW. We truly enjoyed staying here and would do it again. Would recommend to anyone.
Manager response on 2024-11-03 - Response from Best of Key West Rentals
Thank you for your wonderful review Paula. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!

A True Gem

Reviewed by Robert S. on 2024-08-01
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The house was perfect for our needs. Plenty of room for my wife and our two children. Upscale house and furnishings. One of a kind backyard and pool. Extremely spacious for Key West. Quiet and serene locations but perfectly situated and near everything that Key West offers in the way of restaurants, bars, and nightlife. The management team was also very knowledgeable and responsive. Would happily book again.
Manager response on 2024-08-01 - Response from Best of Key West Rentals
Robert thank you for your incredible review! We are so thrilled to hear how much you loved this Key West retreat and we are looking forward to hosting you again next time you visit the island. Thank you for being our guest!

Bright Sunshiny Day

Reviewed by Unknown on 2024-06-24
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
I recently stayed at this vacation rental home and had a fantastic time. The property was clean, well-maintained, and had all the amenities we needed for a comfortable stay. The location was excellent, convenient to local restaurants, and easy to get to Duval. Truman and Co. were highly responsive and accommodating via text or call.
I'm looking forward to our next stay.
Manager response on 2024-06-24 - Response from Best of Key West Rentals
Thank you for this wonderful review Donna, we are so glad you enjoyed the property so much you are planning on coming back! We look forward to welcoming you again next time you are in Key West.

Great home base for enjoying Key West

Reviewed by Dennis E. on 2024-05-02
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This beautiful centrally located home is walkable to the marina, Duval Street, southernmost area allowing a variety of activities without using a vehicle. The home is beautiful and relaxing. The well stocked kitchen has everything we have needed to cook. The backyard privacy, with the foliage, landscaping and pool, make a quiet retreat for pure enjoyment and escape.
Manager response on 2024-05-02 - Response from Best of Key West Rentals
Thank you for your fantastic review Dennis. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

Bright Sunshiny Day

Reviewed by John O. on 2023-09-05
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
BSD is an incredibly beautiful home situated in one of Key Wests best neighborhoods. Everything in the home is high end, new, and well taken care of. The layout of the house is exceptional with one bed and 2 baths down with the main kitchen and den. 2 beds and 2 baths are upstairs with a sitting room and kitchenette in between. The pool and pool area are amazing and so very private. I could not have asked for a better home to have rented for a month.
Manager response on 2023-09-26 - Response from Best of Key West Rentals
We are so happy to read you had such a good stay with us John! Please reach out to us soon to plan your next Key West vacation!

BRIGHT SUNSHINY DAY ~ Renovated 3 BR, 4 Ba Home w/ Pool, Spa & Exercise Room!

Unit Code: BS

BRIGHT SUNSHINY DAY ~ Dreamy!

BRIGHT SUNSHINY DAY ~ Upscale and Perfectly Located 3 Bedroom, 4 Bathroom Home w/ Pool, Spa and Exercise Room!
OLD TOWN CLASSIC... This beautifully redesigned Conch house is in the heart of Key West. Located in the outstanding location of Southard and Ashe Streets, this upscale abode is just minutes from Duval's many restaurants and bars. You are within walking and biking distance to museums, shopping, and Fort Zachary Taylor beach. Come inside this bright and sunny retreat that boasts fully renovated baths and kitchen, wood floors, high ceilings, and Dade County Pine walls. ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS AND AMENITIES… Step into a generous and bright living area that begs you to stay a while. Tropical sunshine floods this space with promises of paradise perfection as you sink into your plush couch in relaxation. Enjoy your favorite shows on the large tv or nap before venturing out on our magical island. Adjacent to the living area is a dine-in kitchen with custom cabinetry and top-end appliances. Craft the perfect meal in this modern and fully stocked cooking space that overlooks the gazebo and small rear garden. Wash your stress away in the exercise studio on the bottom floor that includes an elliptical, peloton bike, free weights and full bath with steam shower for your enjoyment. Travel upstairs where you are greeted by a cozy living area that includes a wet bar with refrigerator drawers and a desk. SLEEPING ARRANGEMENTS… There is a bright and sunny main level queen bedroom with an ensuite shower bathroom which also opens through glass doors to the gazebo and garden. A hanging closet and clothing dresser will hold all of your vacation gear. Upstairs offers two spacious ensuite bedrooms. The king bedroom offers a shower/soaking tub combination, tv, clothing dresser and a wall of glass that opens to a private balcony, painting the room with natural light. The second queen bedroom includes a tv, hanging closet, clothing dresser and glass-door shower bathroom. OUTDOOR LIVING… Enjoy your morning cup of java on the front porch of this lovely tree-lined street, perfect for people watching. In the rear of the home there is a gazebo and lush tropical garden with a sitting space that offers ample seating and a small dining table for eating al fresco. Fire up the grill for your fresh catch or juicy steaks under the sultry stars. The property is surrounded by gorgeous landscaped gardens and a solar heated pool & spa. 4 bikes are available so you can stroll downtown until your heart's content. PARKING... This home has 1 parking spot available for a golf cart however there is plenty of on street parking in the neighborhood. Please refrain from parking in spots marked “residential”. Guests may also park at the Old Town Parking Garage which allows daily / monthly rates. PETS... Small dogs are considered and a pet fee is required. Please inquire prior to booking or make sure to check the box that you are bringing a pet when booking, AND include size, breed, and age of the pet in the comment. MULTI MONTH RESERVATIONS... For monthly reservations, the following fees will be added PER MONTH: Mid-stay clean Pool/hot tub heating fee (if applicable) Pet fee (if applicable) CONCIERGE SERVICES... Enjoy this service to assist you with planning activities for your trip. They can also have your fridge stocked with all the necessities in advance of your arrival! BOOKING DATES... This home is only available as a monthly rental (28 night min.). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. CANCELLATION... Bookings canceled at least 90 days before the start of stay will receive a 100% refund. Cancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).
December 2025
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
January 2026
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
February 2026
SuMoTuWeThFrSa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
Age 18 and under.
DatesPrice
12/15/2025 - 12/31/2025$564 /nt
01/01/2026 - 01/31/2026$804 /nt
02/01/2026 - 02/28/2026$844 /nt
03/01/2026 - 03/31/2026$764 /nt
04/01/2026 - 04/30/2026$572 /nt
05/01/2026 - 07/31/2026$465 /nt
08/01/2026 - 08/31/2026$358 /nt
09/01/2026 - 09/30/2026$447 /nt
10/01/2026 - 10/31/2026$483 /nt
11/01/2026 - 11/30/2026$536 /nt
12/01/2026 - 12/15/2026$625 /nt
5.0000
(7 Review)

Beautiful Place

October 2025
, Lexington, SC United States

Overall
5
Property condition
5
Location
5
Cleanliness
5
Services from rental manager
5

The house and property were excellent. Beautiful pool, great kitchen, and the location was PERFECT! We’d gladly stay here again if it’s available next year.

Manager's Response

Thanks so much for the lovely feedback! We’re happy to hear you enjoyed the property and would love to host you again in the future.

Enjoyed Staying at Bright Sunshiny Day

October 2024
, Asheboro, NC United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This house is wonderful! It is spacious, clean and is in one the best neighborhoods in KW. We truly enjoyed staying here and would do it again. Would recommend to anyone.

Manager's Response

Thank you for your wonderful review Paula. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!

A True Gem

July 2024
, Tallahassee, FL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The house was perfect for our needs. Plenty of room for my wife and our two children. Upscale house and furnishings. One of a kind backyard and pool. Extremely spacious for Key West. Quiet and serene locations but perfectly situated and near everything that Key West offers in the way of restaurants, bars, and nightlife. The management team was also very knowledgeable and responsive. Would happily book again.

Manager's Response

Robert thank you for your incredible review! We are so thrilled to hear how much you loved this Key West retreat and we are looking forward to hosting you again next time you visit the island. Thank you for being our guest!

Bright Sunshiny Day

May 2024
, Jersey City, NJ United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

I recently stayed at this vacation rental home and had a fantastic time. The property was clean, well-maintained, and had all the amenities we needed for a comfortable stay. The location was excellent, convenient to local restaurants, and easy to get to Duval. Truman and Co. were highly responsive and accommodating via text or call.
I'm looking forward to our next stay.

Manager's Response

Thank you for this wonderful review Donna, we are so glad you enjoyed the property so much you are planning on coming back! We look forward to welcoming you again next time you are in Key West.

Bright Sunshiny Day

May 2024
, Jersey City, NJ United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

I recently stayed at this vacation rental home and had a fantastic time. The property was clean, well-maintained, and had all the amenities we needed for a comfortable stay. The location was excellent, convenient to local restaurants, and easy to get to Duval. Truman and Co. were highly responsive and accommodating via text or call.
I'm looking forward to our next stay.

Manager's Response

Thank you for this wonderful review Donna, we are so glad you enjoyed the property so much you are planning on coming back! We look forward to welcoming you again next time you are in Key West.

Great home base for enjoying Key West

April 2024
, erie, CO United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This beautiful centrally located home is walkable to the marina, Duval Street, southernmost area allowing a variety of activities without using a vehicle. The home is beautiful and relaxing. The well stocked kitchen has everything we have needed to cook. The backyard privacy, with the foliage, landscaping and pool, make a quiet retreat for pure enjoyment and escape.

Manager's Response

Thank you for your fantastic review Dennis. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

Bright Sunshiny Day

July 2023
, Mount Pleasant, SC United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

BSD is an incredibly beautiful home situated in one of Key Wests best neighborhoods. Everything in the home is high end, new, and well taken care of. The layout of the house is exceptional with one bed and 2 baths down with the main kitchen and den. 2 beds and 2 baths are upstairs with a sitting room and kitchenette in between. The pool and pool area are amazing and so very private. I could not have asked for a better home to have rented for a month.

Manager's Response

We are so happy to read you had such a good stay with us John! Please reach out to us soon to plan your next Key West vacation!

Leave a Review
3 Bed
4 Baths
Sleeps 6

Search Availability

THE GOOD LIFE ~ Delightful!

THE GOOD LIFE ~ Pet Friendly, Adorable 2nd Floor 1 Bedroom, 1 Bath Condo in Convenient Downtown Location in Truman Annex w/ Community Pool!

Location

204-3 Southard St.
33040 Key West , FL
United States
24° 33' 8.496" N, 81° 48' 17.2584" W
See map: Google Maps
Florida US

THE GOOD LIFE ~ Delightful!

Request More Information

Great value, beautiful location

Reviewed by Unknown on 2025-10-09
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Wonderful unit, close to Duval Street. Plenty of room for 2 people, quiet, clean and tidy. Well equipped for cooking in if you desire, but also close to plenty of nice restaurants and attractions. Property was as described. Some updates to the unit would make it even better!
Manager response on 2025-10-10 - Response from Best of Key West Rentals
Jonathan, thanks so much for the lovely feedback! We’re happy to hear you enjoyed the property and would love to host you again in the future.

Cozy, clean Truman Annex condo, just right !

Reviewed by Patricia C. on 2025-04-06
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We so enjoyed our stay in this clean, comfortable , bright, quiet home in the beautiful Truman Annex neighborhood of just close enough to the beach and downtown , and the folks we met at the community pool were warm and pleasant.
Manager response on 2025-07-24 - Response from Best of Key West Rentals
Thank you so much for your kind words! We're delighted to hear you enjoyed the comfort and cleanliness of the condo, as well as the peaceful charm of the Truman Annex neighborhood. It’s great to know the location was just right and that you had such a pleasant experience at the community pool. We’d love to welcome you back anytime for another relaxing Key West stay!

Perfect Place & Great Location

Reviewed by Unknown on 2025-02-24
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Perfect place for two. Quiet, spacious and great location.
Manager response on 2025-07-24 - Response from Best of Key West Rentals
Thank you for the kind words! We're so glad you found the space quiet, comfortable, and perfectly located. We'd love to host you again anytime!

Cozy retreat

Reviewed by mary c. on 2025-02-16
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We spent three weeks at the good life and thoroughly enjoyed it. Our favorite spot, the balcony, very private, and very comfortable. A great location for Key West Key West
Manager response on 2025-07-24 - Response from Best of Key West Rentals
Thank you for the lovely review! We're so glad you enjoyed your extended stay at The Good Life, especially the private and cozy balcony—it’s such a peaceful spot to unwind. We’re happy the location worked so well for your Key West getaway and would love to welcome you back anytime!

Super Great!

Reviewed by Cindy C. on 2024-12-10
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This unit is very comfortable and offers all the comforts of home. The deck is huge and allows privacy due to all of the beautiful landscaping at Truman Annex. The management team and staff honestly are over the top in their attention and response from the time I booked the property until I checked out. I was absolutely 110% satisfied and I am not usually easy to please.
Manager response on 2025-05-23 - Response from Best of Key West Rentals
Thank you for your wonderful review. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!

The Best Life

Reviewed by leGay C. on 2024-09-22
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This sweet bungalow was a vision of deliciousness the moment we stepped in...the color palette was quintessential Key West! Stayed a week and coming "home" after full days was wonderful.
Manager response on 2025-07-24 - Response from Best of Key West Rentals
Thank you for the lovely review! We're so happy to hear the bungalow felt like a welcoming retreat after your days of exploring. We love that the Key West color palette and cozy vibe made it feel like “home” for the week. We'd be thrilled to welcome you back for another stay in The (Best) Good Life anytime!

A Good Trip to The Good Life

Reviewed by Charles L. on 2024-09-19
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Staying in the Truman Annex is an easy way to experience Key West. Great location, quiet and well maintained property. The unit was excellent for the 2 of us on a week stay. This is slow season because of the brutal heat, potential for storms and lots of places are closed for the month. Plenty to do though, so if smaller crowds are your thing, this would be a great time.
Manager response on 2025-07-24 - Response from Best of Key West Rentals
Thank you for sharing your experience! We're so glad you enjoyed your stay at The Good Life and found the Truman Annex to be a quiet and convenient home base. You're right—while the off-season brings some heat and closures, it’s also the perfect time to enjoy a more relaxed pace and fewer crowds. We’d be happy to welcome you back anytime you’re ready for another Key West escape!

Key West vacation

Reviewed by Dale L. on 2024-07-04
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
we enjoyed our stay at the Shipyard annex, unit 204-3 was nice and had most of what we needed.
Manager response on 2024-07-18 - Response from Best of Key West Rentals
Thank you for your wonderful review Dale. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!

Th Good Life

Reviewed by Agnes A. on 2024-06-12
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This condo was perfect and just the right size for us. The location was perfect and close to everything. It was clean and they had everything we needed for our week stay! We will stay again if we come back to Key West!
Manager response on 2024-07-18 - Response from Best of Key West Rentals
Thank you for this great review Agnes! We are thrilled you enjoyed the property and hope to host you again in the future!

Great Stay

Reviewed by Peter Y. on 2024-05-12
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We've stayed in Truman Annex the last four years and it is a great location. This was perfect for the 2 of us. everything was as described and we loved it.

We did have an issue with the electronic lock on the last day, and while the electronic lock is great - don't have to worry about forgetting a key - when it doesn't work you are locked out with no recourse. Fortunately it was the morning of our departure and we were just getting ready to leave, so we can't comment on how long it might take for something like that to get resolved.
Manager response on 2024-07-18 - Response from Best of Key West Rentals
Thank you for this great review! We are thrilled you enjoyed the property! We resolve any issue within a few hours when possible. The lock resets after check out time and each guest gets their own code. In the event guests forget the code or are locked out, the property manager would be able to open the unit using our secured system. please feel free to ask any questions before, during and after your stay, we hope to host you again in the future and want you to feel confident our rental meets all your needs. Thank you for being our guest!

The Good Life

Reviewed by Christy K. on 2024-05-05
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The location of The Good Life is perfect! Close to all the places we like to go. The condo is very small but perfect for two. It was very clean. The bath and kitchen are updated and very nice. Kitchen was well appointed. The furnishings are not good. Sooo outdated and worn. The king bed was very comfortable but needs a headboard that is king size. Queen size doesn't cut it. The carpeting just needs to go away. It's awful. The balcony is lovely! Spacious and so private. Our property manager was great! So helpful and always returned our calls immediately.
Manager response on 2024-07-18 - Response from Best of Key West Rentals
Thank you for your incredible review Christy! We are so thrilled to hear how much you loved this Key West retreat and we are looking forward to hosting you again next time you visit the island. Thank you for being our guest!

Key West Getaway

Reviewed by Melissa M. on 2024-04-14
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We had an amazing trip! The condo was perfect. The pool was great. The Property Manager, Melanie, went above and beyond to help up! We back!!
Manager response on 2024-07-18 - Response from Best of Key West Rentals
Thank you for your fantastic review Melissa. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

Relaxing

Reviewed by James F. on 2024-02-20
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
A great location and clean area.
Manager response on 2024-07-18 - Response from Best of Key West Rentals
Thank you for your fantastic review James. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

Cozy Getaway

Reviewed by Laura P. on 2023-12-20
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Our cozy apartment was perfectly located within the Truman Annex . We were just a couple of blocks away from the crowds on Duvall, Mallory Square, and the Fort complex. It was so quiet and peaceful at the annex, and we felt very safe. We weren’t that far from the Harbor Walk and walked there as well for our snorkel trip. When we needed a ride to Smathers Beach or elsewhere, we hailed an Uber or taxi. The apartment was clean and well furnished. We enjoyed being able to make our own breakfast and coffee in the morning. Having a washer and dryer was helpful as well.
Manager response on 2024-07-18 - Response from Best of Key West Rentals
Thank you for your fantastic review Laura. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

The Good Life is true to its name.

Reviewed by Charles M. on 2023-07-05
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Great experience. The property manager was on top of any question we had. The unit was stocked better than we have ever had. Great location.
Manager response on 2023-12-13 - Response from Best of Key West Rentals
Thank you for sharing a review of your recent experience Charles. Our team here at Best of Key West Rentals is committed to providing high-quality guest service, and we’re thrilled to hear that we made a good impression on you. We hope you’ll visit us again soon.

Cozy Getaway

Reviewed by Michael W. on 2023-05-04
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The home was beautifully decorated, comfortable, and quite private for being in a complex. Great location for staying on foot/bike for the whole week. Property manager was very quick and attentive to my questions...highly recommended!
Manager response on 2023-12-05 - Response from Best of Key West Rentals
Thank you for this great review! We are thrilled you enjoyed the property and hope to host you again in the future!

THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo!

Unit Code: GL

THE GOOD LIFE ~ Delightful!

THE GOOD LIFE ~ Pet Friendly, Adorable 2nd Floor 1 Bedroom, 1 Bath Condo in Convenient Downtown Location in Truman Annex w/ Community Pool!
COZY VALUE IN TRUMAN ANNEX… This 2nd Floor one bedroom, one bath condo is located in The Shipyard, a neighborhood of the coveted Truman Annex in the heart of Old Town Key West! You will be in walking distance from Fort Zachary’s gorgeous beach and picnic area, Duval Street, Mallory Square and more! Throw your cares to the wind as you unwind in this charming, tree-shrouded neighborhood with walking paths and lanes. This small but sensational gem is an upstairs unit with all of the creature comforts you will need in paradise! ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE DETAILS AND AMENITIES... Easy breezy comfort greets you as you enter this charming home. Travel up the carpeted stairs to a bright and cheerful open living room and kitchen/dining space. Unwind on the plush furnishings as cheerful sunlight floods the living room and creates a happy and carefree environment. A smart TV offers a wide array of programming for your viewing indulgence. The dining/kitchen area is adjacent to the living room, with a dining table nearby. The kitchen is fully equipped with a dishwasher, stove, microwave, refrigerator and both a Keurig and drip coffee maker. The cabinets are stocked with every kitchen tool you will need to craft delicious meals. SLEEPING ARRANGEMENTS… Unwind from your day of island fun in the king bedroom. A wall-mounted smart tv is available for lazy days when it just feels right to linger in your cozy bedding and binge on your favorite shows. The storage closet houses a fold-up twin bed and extra bath linens for your enjoyment. The bathroom is next door with a glass-door shower and a washer/dryer closet is adjacent to it for your convenience. OUTDOOR LIVING… The Shipyard offers a beautiful community pool lined with lounge chairs perfect for soaking up the sun. Open the French door to the roomy private terrace, inviting sultry breezes and Key West sunshine inside. This wonderful extension to the living space has a table for 2 where you can have your morning coffee or enjoy a cocktail after a long day of exploring. There are also 2 more cushioned wicker chairs for lounging outdoors. PARKING... This home does offer parking for one vehicle (vehicle cannot exceed 18 ft), but oversized trucks and extra large SUVs are not permitted and will have to park outside of this community. PETS... This is a pet friendly home with a required pet fee. Please include the size and breed when inquiring. MULTI MONTH RESERVATIONS... For monthly reservations, the following fees will be added PER MONTH: Mid-stay clean Pet fee BOOKING DATES... This home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. CANCELLATION... Bookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund. CONCIERGE SERVICES... Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival! COME STAY A WHILE...
December 2025
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
January 2026
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
February 2026
SuMoTuWeThFrSa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
Age 18 and under.
DatesPrice
12/15/2025 - 12/15/2025$124 /nt
12/16/2025 - 12/16/2025$116 /nt
12/17/2025 - 12/17/2025$138 /nt
12/18/2025 - 12/18/2025$147 /nt
12/19/2025 - 12/19/2025$176 /nt
12/20/2025 - 12/20/2025$178 /nt
12/21/2025 - 12/21/2025$194 /nt
12/22/2025 - 12/22/2025$196 /nt
12/23/2025 - 12/23/2025$198 /nt
12/24/2025 - 12/24/2025$233 /nt
12/25/2025 - 12/25/2025$264 /nt
12/26/2025 - 12/26/2025$291 /nt
12/27/2025 - 12/27/2025$309 /nt
12/28/2025 - 12/28/2025$392 /nt
12/29/2025 - 12/29/2025$419 /nt
12/30/2025 - 12/30/2025$425 /nt
12/31/2025 - 12/31/2025$431 /nt
01/01/2026 - 01/02/2026$250 /nt
01/03/2026 - 01/31/2026$233 /nt
02/01/2026 - 02/28/2026$304 /nt
03/01/2026 - 04/30/2026$250 /nt
05/01/2026 - 07/31/2026$143 /nt
08/01/2026 - 08/01/2026$371 /nt
08/02/2026 - 08/02/2026$300 /nt
08/03/2026 - 08/03/2026$226 /nt
08/04/2026 - 08/04/2026$222 /nt
08/05/2026 - 08/05/2026$229 /nt
08/06/2026 - 08/06/2026$274 /nt
08/07/2026 - 08/07/2026$308 /nt
08/08/2026 - 08/08/2026$315 /nt
08/09/2026 - 08/09/2026$245 /nt
08/10/2026 - 08/10/2026$221 /nt
08/11/2026 - 08/11/2026$213 /nt
08/12/2026 - 08/12/2026$219 /nt
08/13/2026 - 08/13/2026$262 /nt
08/14/2026 - 08/14/2026$297 /nt
08/15/2026 - 08/15/2026$295 /nt
08/16/2026 - 08/16/2026$219 /nt
08/17/2026 - 08/17/2026$194 /nt
08/18/2026 - 08/18/2026$184 /nt
08/19/2026 - 08/19/2026$190 /nt
08/20/2026 - 08/20/2026$243 /nt
08/21/2026 - 08/21/2026$287 /nt
08/22/2026 - 08/22/2026$289 /nt
08/23/2026 - 08/23/2026$221 /nt
08/24/2026 - 08/24/2026$201 /nt
08/25/2026 - 08/25/2026$196 /nt
08/26/2026 - 08/26/2026$199 /nt
08/27/2026 - 08/27/2026$250 /nt
08/28/2026 - 08/28/2026$292 /nt
08/29/2026 - 08/29/2026$330 /nt
08/30/2026 - 08/30/2026$221 /nt
08/31/2026 - 08/31/2026$196 /nt
09/01/2026 - 09/01/2026$230 /nt
09/02/2026 - 09/02/2026$232 /nt
09/03/2026 - 09/03/2026$279 /nt
09/04/2026 - 09/04/2026$350 /nt
09/05/2026 - 09/05/2026$352 /nt
09/06/2026 - 09/06/2026$286 /nt
09/07/2026 - 09/07/2026$259 /nt
09/08/2026 - 09/08/2026$184 /nt
09/09/2026 - 09/09/2026$186 /nt
09/10/2026 - 09/10/2026$233 /nt
09/11/2026 - 09/11/2026$273 /nt
09/12/2026 - 09/12/2026$277 /nt
09/13/2026 - 09/13/2026$215 /nt
09/14/2026 - 09/14/2026$188 /nt
09/15/2026 - 09/15/2026$176 /nt
09/16/2026 - 09/16/2026$189 /nt
09/17/2026 - 09/17/2026$237 /nt
09/18/2026 - 09/18/2026$276 /nt
09/19/2026 - 09/19/2026$284 /nt
09/20/2026 - 09/20/2026$220 /nt
09/21/2026 - 09/21/2026$196 /nt
09/22/2026 - 09/22/2026$188 /nt
09/23/2026 - 09/23/2026$204 /nt
09/24/2026 - 09/24/2026$249 /nt
09/25/2026 - 09/25/2026$289 /nt
09/26/2026 - 09/26/2026$295 /nt
09/27/2026 - 09/27/2026$230 /nt
09/28/2026 - 09/28/2026$204 /nt
09/29/2026 - 09/29/2026$186 /nt
09/30/2026 - 09/30/2026$209 /nt
10/01/2026 - 10/01/2026$253 /nt
10/02/2026 - 10/02/2026$296 /nt
10/03/2026 - 10/03/2026$301 /nt
10/04/2026 - 10/04/2026$237 /nt
10/05/2026 - 10/05/2026$207 /nt
10/06/2026 - 10/06/2026$193 /nt
10/07/2026 - 10/07/2026$206 /nt
10/08/2026 - 10/08/2026$256 /nt
10/09/2026 - 10/09/2026$314 /nt
10/10/2026 - 10/10/2026$326 /nt
10/11/2026 - 10/11/2026$260 /nt
10/12/2026 - 10/12/2026$231 /nt
10/13/2026 - 10/13/2026$207 /nt
10/14/2026 - 10/14/2026$219 /nt
10/15/2026 - 10/15/2026$275 /nt
10/16/2026 - 10/16/2026$374 /nt
10/17/2026 - 10/17/2026$381 /nt
10/18/2026 - 10/18/2026$316 /nt
10/19/2026 - 10/19/2026$288 /nt
10/20/2026 - 10/20/2026$276 /nt
10/21/2026 - 10/21/2026$288 /nt
10/22/2026 - 10/22/2026$338 /nt
10/23/2026 - 10/23/2026$376 /nt
10/24/2026 - 10/24/2026$382 /nt
10/25/2026 - 10/25/2026$338 /nt
10/26/2026 - 10/26/2026$233 /nt
10/27/2026 - 10/27/2026$227 /nt
10/28/2026 - 10/28/2026$239 /nt
10/29/2026 - 10/29/2026$285 /nt
10/30/2026 - 10/30/2026$701 /nt
10/31/2026 - 10/31/2026$702 /nt
11/01/2026 - 11/01/2026$639 /nt
11/02/2026 - 11/02/2026$611 /nt
11/03/2026 - 11/03/2026$608 /nt
11/04/2026 - 11/04/2026$619 /nt
11/05/2026 - 11/05/2026$662 /nt
11/06/2026 - 11/06/2026$695 /nt
11/07/2026 - 11/07/2026$703 /nt
11/08/2026 - 11/08/2026$641 /nt
11/09/2026 - 11/09/2026$604 /nt
11/10/2026 - 11/10/2026$307 /nt
11/11/2026 - 11/11/2026$300 /nt
11/12/2026 - 11/12/2026$290 /nt
11/13/2026 - 11/13/2026$318 /nt
11/14/2026 - 11/14/2026$330 /nt
11/15/2026 - 11/15/2026$271 /nt
11/16/2026 - 11/16/2026$239 /nt
11/17/2026 - 11/17/2026$238 /nt
11/18/2026 - 11/18/2026$252 /nt
11/19/2026 - 11/19/2026$292 /nt
11/20/2026 - 11/20/2026$307 /nt
11/21/2026 - 11/21/2026$327 /nt
11/22/2026 - 11/22/2026$266 /nt
11/23/2026 - 11/23/2026$303 /nt
11/24/2026 - 11/24/2026$296 /nt
11/25/2026 - 11/25/2026$307 /nt
11/26/2026 - 11/26/2026$337 /nt
11/27/2026 - 11/27/2026$362 /nt
11/28/2026 - 11/28/2026$377 /nt
11/29/2026 - 11/29/2026$256 /nt
11/30/2026 - 11/30/2026$229 /nt
12/01/2026 - 12/01/2026$226 /nt
12/02/2026 - 12/02/2026$240 /nt
12/03/2026 - 12/03/2026$272 /nt
12/04/2026 - 12/04/2026$303 /nt
12/05/2026 - 12/05/2026$318 /nt
12/06/2026 - 12/06/2026$273 /nt
12/07/2026 - 12/07/2026$245 /nt
12/08/2026 - 12/08/2026$238 /nt
12/09/2026 - 12/09/2026$242 /nt
12/10/2026 - 12/10/2026$273 /nt
12/11/2026 - 12/11/2026$307 /nt
12/12/2026 - 12/12/2026$323 /nt
12/13/2026 - 12/13/2026$283 /nt
12/14/2026 - 12/14/2026$282 /nt
12/15/2026 - 12/15/2026$265 /nt
4.9444
(18 Review)

Great value, beautiful location

September 2025
, Panama City, FL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
3

Wonderful unit, close to Duval Street. Plenty of room for 2 people, quiet, clean and tidy. Well equipped for cooking in if you desire, but also close to plenty of nice restaurants and attractions. Property was as described. Some updates to the unit would make it even better!

Manager's Response

Jonathan, thanks so much for the lovely feedback! We’re happy to hear you enjoyed the property and would love to host you again in the future.

Cozy, clean Truman Annex condo, just right !

March 2025
, New Rochelle, NY US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We so enjoyed our stay in this clean, comfortable , bright, quiet home in the beautiful Truman Annex neighborhood of just close enough to the beach and downtown , and the folks we met at the community pool were warm and pleasant.

Manager's Response

Thank you so much for your kind words! We're delighted to hear you enjoyed the comfort and cleanliness of the condo, as well as the peaceful charm of the Truman Annex neighborhood. It’s great to know the location was just right and that you had such a pleasant experience at the community pool. We’d love to welcome you back anytime for another relaxing Key West stay!

Perfect Place & Great Location

January 2025
, Morgantown, WV United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Perfect place for two. Quiet, spacious and great location.

Manager's Response

Thank you for the kind words! We're so glad you found the space quiet, comfortable, and perfectly located. We'd love to host you again anytime!

Cozy retreat

January 2025
, Toledo, OH US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We spent three weeks at the good life and thoroughly enjoyed it. Our favorite spot, the balcony, very private, and very comfortable. A great location for Key West Key West

Cozy retreat

January 2025
, Port Clinton, OH United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We spent three weeks at the good life and thoroughly enjoyed it. Our favorite spot, the balcony, very private, and very comfortable. A great location for Key West Key West

Manager's Response

Thank you for the lovely review! We're so glad you enjoyed your extended stay at The Good Life, especially the private and cozy balcony—it’s such a peaceful spot to unwind. We’re happy the location worked so well for your Key West getaway and would love to welcome you back anytime!

Super Great!

November 2024
, Panama City Beach, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This unit is very comfortable and offers all the comforts of home. The deck is huge and allows privacy due to all of the beautiful landscaping at Truman Annex. The management team and staff honestly are over the top in their attention and response from the time I booked the property until I checked out. I was absolutely 110% satisfied and I am not usually easy to please.

Manager's Response

Thank you for your wonderful review. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!

A Good Trip to The Good Life

September 2024
, Fredericksburg, TX United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Staying in the Truman Annex is an easy way to experience Key West. Great location, quiet and well maintained property. The unit was excellent for the 2 of us on a week stay. This is slow season because of the brutal heat, potential for storms and lots of places are closed for the month. Plenty to do though, so if smaller crowds are your thing, this would be a great time.

Manager's Response

Thank you for sharing your experience! We're so glad you enjoyed your stay at The Good Life and found the Truman Annex to be a quiet and convenient home base. You're right—while the off-season brings some heat and closures, it’s also the perfect time to enjoy a more relaxed pace and fewer crowds. We’d be happy to welcome you back anytime you’re ready for another Key West escape!

The Best Life

August 2024
, MELBOURNE, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This sweet bungalow was a vision of deliciousness the moment we stepped in...the color palette was quintessential Key West! Stayed a week and coming "home" after full days was wonderful.

Manager's Response

Thank you for the lovely review! We're so happy to hear the bungalow felt like a welcoming retreat after your days of exploring. We love that the Key West color palette and cozy vibe made it feel like “home” for the week. We'd be thrilled to welcome you back for another stay in The (Best) Good Life anytime!

Key West vacation

June 2024
, Houma, LA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

we enjoyed our stay at the Shipyard annex, unit 204-3 was nice and had most of what we needed.

Manager's Response

Thank you for your wonderful review Dale. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!

Th Good Life

June 2024
, Montgomery, AL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This condo was perfect and just the right size for us. The location was perfect and close to everything. It was clean and they had everything we needed for our week stay! We will stay again if we come back to Key West!

Manager's Response

Thank you for this great review Agnes! We are thrilled you enjoyed the property and hope to host you again in the future!

Great Stay

May 2024
, Annapolis, MD United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We've stayed in Truman Annex the last four years and it is a great location. This was perfect for the 2 of us. everything was as described and we loved it.

We did have an issue with the electronic lock on the last day, and while the electronic lock is great - don't have to worry about forgetting a key - when it doesn't work you are locked out with no recourse. Fortunately it was the morning of our departure and we were just getting ready to leave, so we can't comment on how long it might take for something like that to get resolved.

Manager's Response

Thank you for this great review! We are thrilled you enjoyed the property! We resolve any issue within a few hours when possible. The lock resets after check out time and each guest gets their own code. In the event guests forget the code or are locked out, the property manager would be able to open the unit using our secured system. please feel free to ask any questions before, during and after your stay, we hope to host you again in the future and want you to feel confident our rental meets all your needs. Thank you for being our guest!

Great Stay

May 2024
, ANNAPOLIS, MD United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We've stayed in Truman Annex the last four years and it is a great location. This was perfect for the 2 of us. everything was as described and we loved it.

We did have an issue with the electronic lock on the last day, and while the electronic lock is great - don't have to worry about forgetting a key - when it doesn't work you are locked out with no recourse. Fortunately it was the morning of our departure and we were just getting ready to leave, so we can't comment on how long it might take for something like that to get resolved.

Manager's Response

Thank you for this great review! We are thrilled you enjoyed the property! We resolve any issue within a few hours when possible. The lock resets after check out time and each guest gets their own code. In the event guests forget the code or are locked out, the property manager would be able to open the unit using our secured system. please feel free to ask any questions before, during and after your stay, we hope to host you again in the future and want you to feel confident our rental meets all your needs. Thank you for being our guest!

The Good Life

April 2024
, Oden, MI US

Overall
4
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

The location of The Good Life is perfect! Close to all the places we like to go. The condo is very small but perfect for two. It was very clean. The bath and kitchen are updated and very nice. Kitchen was well appointed. The furnishings are not good. Sooo outdated and worn. The king bed was very comfortable but needs a headboard that is king size. Queen size doesn't cut it. The carpeting just needs to go away. It's awful. The balcony is lovely! Spacious and so private. Our property manager was great! So helpful and always returned our calls immediately.

Manager's Response

Thank you for your incredible review Christy! We are so thrilled to hear how much you loved this Key West retreat and we are looking forward to hosting you again next time you visit the island. Thank you for being our guest!

Key West Getaway

March 2024
, Cloverdale, VA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We had an amazing trip! The condo was perfect. The pool was great. The Property Manager, Melanie, went above and beyond to help up! We back!!

Manager's Response

Thank you for your fantastic review Melissa. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

Relaxing

January 2024
, Bloomington, IL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

A great location and clean area.

Manager's Response

Thank you for your fantastic review James. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

Cozy Getaway

November 2023
, Gresham, OR US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

Our cozy apartment was perfectly located within the Truman Annex . We were just a couple of blocks away from the crowds on Duvall, Mallory Square, and the Fort complex. It was so quiet and peaceful at the annex, and we felt very safe. We weren’t that far from the Harbor Walk and walked there as well for our snorkel trip. When we needed a ride to Smathers Beach or elsewhere, we hailed an Uber or taxi. The apartment was clean and well furnished. We enjoyed being able to make our own breakfast and coffee in the morning. Having a washer and dryer was helpful as well.

Manager's Response

Thank you for your fantastic review Laura. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!

The Good Life is true to its name.

June 2023
, Marietta, GA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Great experience. The property manager was on top of any question we had. The unit was stocked better than we have ever had. Great location.

Manager's Response

Thank you for sharing a review of your recent experience Charles. Our team here at Best of Key West Rentals is committed to providing high-quality guest service, and we’re thrilled to hear that we made a good impression on you. We hope you’ll visit us again soon.

Cozy Getaway

April 2023
, Albuquerque, NM US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The home was beautifully decorated, comfortable, and quite private for being in a complex. Great location for staying on foot/bike for the whole week. Property manager was very quick and attentive to my questions...highly recommended!

Manager's Response

Thank you for this great review! We are thrilled you enjoyed the property and hope to host you again in the future!

Leave a Review
1 Bed
1 Bath
Sleeps 2

Search Availability

Pages

Subscribe to Best of Key West Rentals RSS