Row Wrapper 2

BAHAMA DREAMING ~ Live Local!

4.9412
(34 Reviews)

Capacity

3 Bedrooms
2 Bath
Sleeps 8

Search Availability

About

BEGIN YOUR ISLAND ESCAPE...
Come get lost in the magic of this captivating island retreat offering modern amenities within this old-world, historic setting. Savor sweet moments with your loved ones while enjoying a simple agenda, lounging indoors or tooling around town by foot to all the highly sought-after Key West attractions.
***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE

DETAILS & AMENITIES...
Step off your private porch into your peaceful escape boasting rich, hardwood flooring, inviting you inside. A homey living room featuring beautiful wooden beams is outfitted with cozy furnishings around a flat screen TV for your movie or game nights together. A cheerful and fully equipped kitchen lies steps away to whip up your home cooked meals at the casual indoor bistro table for 2 or out with the whole gang on the covered porch dining table for 6.

SLEEPING ARRANGEMENTS...
Settle into a good night’s rest in the guest room with two twins, which can convert to a king upon request. A comfortable queen guestroom is just down the hall. Follow the stairs to the 2nd floor king suite with an en suite bathroom with a shower/tub combination. Each guest room comes with a flat screen TV for your daily dose of media. A sofa sleeper resides in the living room with convenience to an adjacent bathroom with a shower.

OUTDOOR LIVING...
Catch some rays out on your back deck in one of the loungers as you soak up your serene surroundings with lush vegetation swaying in the breeze. Grill up your fresh catch of the day after your refreshing swim in the private pool(comes heated in the cooler months) as you plan out your evening on the town. Located in an incredibly diverse and upbeat hotspot, this home is just a stone’s throw to all the favorite bars, restaurants, the local's favorite grocery spot and and all the sights to see!

PARKING...
Enjoy the perk of a parking space for a small to medium sized vehicle.

PETS…
Dogs are considered at this home.

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 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.

THERE’S NO PLACE LIKE KEY WEST...

Features

Amenities

  • Parking
  • Free Wifi
  • Coffee Maker
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Heated Pool
  • Private Pool
  • Central Air
  • Washer & Dryer
  • Gas Grill

Rental Type and Location

  • House
  • Old Town

Pet Friendly

  • Yes

Duration

  • Nightly

Availability

Key
#Night Available#Night Unavailable#Arrive Only#Depart Only
February 2025
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October 2025
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January 2026
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Map

Reviews

Roomy House in Great location

February 2025
, New Lenox, IL US

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

House was close to Duval Street, but far enough away to avoid noise. Nice pool for kids to swim in.

Bahanma Dreaming visit

October 2024
, Adamsville, TN Unknown

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

The location was fantastic! Did not like the YouTube TV. Two baths for 3 bedrooms makes it tough. Overall though, positive.

Manager's Response

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

Great location and property

October 2024
, Burlington, MA United States

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

We were two couples traveling for a 5-day getaway. The house was in a fantastic location one block off of Duval and next door to a grocery store and a few breakfast places and other restaurants to make getting food very convenient.
We had some issues with sugar ants in the kitchen when some food we purchased was inundated with them but the property manager responded VERY quickly and had the pest control company out there right away to treat. It's Florida, so if you're from anywhere not tropical know that bugs are a thing down there.
The property manager (Shana) was extremely responsive to any inquiries.
The house was clean, had plenty of towels and kitchen items to make the stay comfortable, and the covered porch in the backyard was definitely our favorite and allowed us to be outside even in rainstorms.
We'd absolutely stay here again when returning to Key West.

Manager's Response

We are so happy to read you had such a good stay with us! We would love to welcome you back!

Fabulous Key West Getaway

September 2024
, Charlotte, NC US

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

We had an awesome time at this quaint Ket West home. The home had lots of character. It was very clean and maintained. Location was perfect...near Duval nightlife, local grocery and great cafes and restaurants. The outside pool area was nice to come home after a hot day of walking the streets. I would love to return as soon as possible. The management company was in touch most days and were very prompt replying to texts. We were there with Hurricane Helene looming and let us know to call if we needed anything. Definitely recommend!!!

Manager's Response

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

Great house!

September 2024
, Boca Raton, FL US

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

We had a great time at this lovely three bedroom cottage. Roomy and well appointed. Pool was excellent - shady and private. Close to Duval and all the K-W attractions, bars, music and restaurants.

Manager's Response

We are so happy to read you had such a good stay with us! We would love to welcome you back!

Family Business Trip

August 2024
, Lebanon, OH US

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

They home was cozy and very convenient to Duvall St. It was clean and well supplied with essentials. We enjoyed our stay.

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!

Great Location

July 2024
, Naples , FL United States

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

We had a great time at Bahama Dreaming. The location was great! Would stay at this location again. Will definitely use Truman and Company in the future. Their communication was fantastic!

Manager's Response

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

2nd try....great place

July 2024
, Roswell, GA US

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

This was an absolute perfect place for us. Coupled with week long scooter rental at Pirate Scooters, and small pool, made for a perfect trip

Manager's Response

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

Family Trip

June 2024
, Panama City, Florida, FL United States

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

This is the 3rd house we've rented from Truman & Company and were very pleased with it. Great Location, could walk to everything. Plenty of room for 7 of us.
Very quiet, only the roosters woke us up in the morning LOL.

Manager's Response

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

Dreamy Stay

April 2024
, ludlow, VT United States

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

This was a perfect vacation spot for our family of 5. With two rooms for the kids & a seperate bathroom and a primary suite upstairs w/ a bath and closet everyone was content and there was no arguing over sharing beds. The outdoor covered porch with large table was our favorite spot to gather after a morning at the beach. property was extremely clean and there were plenty of linens and towels - Location was great - close to duval but far enough away for privacy and no noise at night. property management service was outstanding with quick response time and accomodated us with every need. would recommend them again

Manager's Response

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

Great location

March 2024
, Grand Rapids, MI US

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

Has been updated since last stay and now is more pleasant looking. Counters in the kitchen are in pretty bad shape but functional. Pool is wonderful to have and maintenance is good. Too much shade for our liking. Brick missing by front door causing stubbed toes. Overall still a great place to stay.

Manager's Response

Kathleen thank you for reviewing your stay, we are glad you overall enjoyed your stay. I have shared the brick issue with my team who will fix is right away. Thank you for being our guest!

FAMILY TRIP

March 2024
, South Yarmouth, MA US

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

This was the perfect size for our family of six. Very spacious, walking distance to Duval Street and other attractions. It is not a quiet spot. Dumpsters get emptied way before sun rise. And there is a grocery store on the opposite corner that obviously receives truck loads of goods. Book direct, no need to go through VRBO; think it would save money. Property manager is very attentive and available.

Manager's Response

We are so happy to read you had such a good stay with us! We would love to welcome you back!

Review of Bahama Dreaming

February 2024
, Erlanger, KY US

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

Great space and location. A short walk to Duvall, grocery, and some quick eats. Perfect for our group.

Manager's Response

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

Wonderful home in the heart of Key West

February 2024
, Haverstraw, NY United States

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

We stayed here for four nights with 4 adults (2 couples) and had a wonderful time. The home was beautiful, clean, well-decorated, and up to date. It is very nice to have an entire private home to yourselves and not have to share amenities or space with others. The highlight of the property is certainly the palm-lined backyard with the pool, hammock, and covered dining area on the deck - like your own private oasis! Location really cannot be beat - it is so close to downtown restaurants and night life while also being walking distance to Ft. Zachary Taylor State Park, southernmost point, and other sites. Televisions were logged into YouTube TV which was an added bonus. Property managers were kind and easily contacted. They allowed us to check in about 3 hours early (as soon as the house was ready after being cleaned). Check out time was earlier than expected at 10am. There is luggage storage available (for a fee of ~$15 per bag) at a gift shop 2 blocks away.

The only downside I can feasibly point out is that while the house itself is private and well-located, there are small parking areas on either side of the house and there is a grocery store loading area directly across the street -- this did not bother us much, however there seemed to always be some sort of activity in these areas, often at early hours of the morning (e.g. 5am dumpster emptying in the adjacent parking lot, 6am deliveries via tractor trailer at the grocery store). For the most part it really was not an issue, but it was not always quiet. As a side note -- any visitor to Key West should know that roosters are a part of the city, and their crowing will also add to the early morning noise, but that is not something I would complain about since I think that is part of the charm!

Manager's Response

Thank you for taking the time to review your stay. We are thrilled you enjoyed your stay with us and hope to welcome you again next time you visit paradise!

Paradise

December 2023
, boca raton, FL US

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

What a wonderful house in a perfect location! Loved this place and the serene backyard with heated pool. I would definitely stay here again.

Manager's Response

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

Great trip

October 2023
, Du Quoin, IL United States

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

Everything was great. It was the cleanest place we’ve ever stayed. Property manager responded within minutes every time we needed something. We will be back.

Manager's Response

Thank you for taking the time to review your stay Jordan. We are thrilled you enjoyed your stay with us and hope to welcome you again next time you visit paradise!

Great Getaway

September 2023
, Lakeland, GA United States

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

The home was in the perfect location, and was still private. Had all the amenities and was very enjoyable no matter which room you stay in. Management was extremely polite and very attentive. I plan to stay here again and recommend others do too.

Manager's Response

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

Lobster Fest in Key West

August 2023
, ellenton, FL US

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

Great little house steps from Duval Street. This historic home was a great find. Very clean and very cool on a hot summer trip to the Keys. The pool was shaded nicely so it felt secluded and help keep the pool temp down. The property manager was responsive and extremely helpful!

Manager's Response

We are so happy to read you had such a good stay with us Laura! We would love to welcome you back!

Perfect Key West escape

July 2023
, Providence Forge, VA US

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

This home was perfect for our family of 7. Plenty of room to stretch out. We were so pleased with the pool and porch area that we found ourselves hanging out there every day. The location was perfect, one block off the center of Duval, with easy walking to shops and restaurants. Also, we were just 4 houses away from the market making it easy to get food and beverages. We appreciated the washer/dryer, as we didn't need to pack so much. We would absolutely rent this house again!


Manager's Response

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

Stop scrolling and Book

June 2023
, Brentwood, TN US

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

Immaculately clean, charming, walking distance to downtown this place has it all. My family of 6 stayed here comfortably. Duval street is practically right out the door but the serene backyard with pool and lush tropical landscaping you feel like you are miles away in your own secluded paradise. Concierge and property manager were extremely efficient and were just a text away.

Manager's Response

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

Key west

May 2023
, Saint Petersburg, FL United States

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

We had a super time ! House was cute and location was super ! Very glad they are dog friendly ! Excellent attention by our Truman Co rep! Excellent experience !

Manager's Response

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

Key west

May 2023
, St Petersburg, FL United States

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

We had a super time ! House was cute and location was super ! Very glad they are dog friendly ! Excellent attention by our Truman Co rep! Excellent experience !

Manager's Response

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

Awesome stay

April 2023
, Fountain, FL US

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

The house was cozy, well stocked, conveniently located in the middle of everything yet private and secluded at the same time. The property management company was great to work with. We loved everything about staying here!!

Manager's Response

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

AMAZING!!!

February 2023
, Providence, RI United States

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

This place was a wonderful place to stay! Loved being so close to all the attractions. The house was so relaxing and well stocked. The poll was great to come home and sit in to relax.

Manager's Response

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

Close to Duval

November 2022
, Yellville, AR US

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

House is one block behind Willie T’s. So close to the middle of Duval which was great. This is so far the best VRBO house we have rented in key west.

Manager's Response

Thank you for taking the time to post a review of our property Melissa. We are so happy to hear that you enjoyed your time in Key West. 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.

Secluded spot close to everything!

November 2022
, Homewood, IL United States

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

We loved Bahama Dreaming for it's location 1 block off Duval, but it also felt like it was miles away when you walked into the back deck. Everything was perfect and we'd definitely stay again.

Manager's Response

We are so happy to read you had such a good stay with us Nathan! We would love to welcome you back!

Perfect Location

October 2022
, East Aurora, NY United States

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

House is perfectly located across the street from Fausto's Grocery Store and just around the corner from Duval. Property manager was very attentive and helpful through the entire stay. House was very clean and back porch was perfect spot to hang out when at the house. Would highly recommend!!

Manager's Response

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

Peaceful & relaxing!

September 2022
, Lake Worth, FL US

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

They were so accommodating. We were in town for a memorial and I was a great place for us all to relax in a peaceful place. Thank you!

Manager's Response

Thank you for your wonderful review Monica. We are happy to have been able to provide you with the right home to help you go through a difficult time. We hope to welcome you in better circumstances in the future. Thank you for trusting us!

Family/Birthday Celebration

August 2022
, Valrico, FL United States

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

Brian, the property manager, was incredibly responsive and communicated at every turn. We did have one minor issue with an air conditioner leaking upstairs due to a clogged drain line. I let him know and he had a technician out ASAP and handled it for us quickly. Would absolutely love to reserve this property again!

Manager's Response

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

Awesome Keys Trip!!!

July 2022
, Jacksonville, FL US

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

This house is perfect! It’s an easy walk to Duval Street, a grocery store, and everything else you need. The pool is a great way to cool off on a hot summer day! To top it off, the management is fantastic and a pleasure to deal with. Highly recommend!!!!

Manager's Response

Thank you for your incredible review Patrick! 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

May 2022
, York, ME United States

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

Excellent!

Manager's Response

Thank you for your review Adeline, we are glad you had an excellent stay and hope to host you again next time you visit Key West!

Key West

May 2022
, York, ME US

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

Excellent!

Manager's Response

Thank you for your review Adeline, we are glad you had an excellent stay and hope to host you again next time you visit Key West!

Amazing House and Perfect Location

April 2022
, Wilmington, DE US

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

We rented this house for a family vacation. We had 6 adults and 2 toddlers. The house was spacious and had the perfect layout so everyone was comfortable. The pool was an incredible added bonus and we spent a lot of time enjoying the entire outside setup. The location was also perfect. The house was in a relatively quiet area and all we had to do was walk one block to enjoy Duval Street. Mallory Square was also easily accessible. Finally, Brian (property manager) was proactive in ensuring my stay was smooth and was very responsive to my questions. I would definitely rent this hour again and recommend to anyone.

Manager's Response

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

Great stay in Key West

April 2022
, Johns island, SC US

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

Excellent

Manager's Response

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