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Condo

A Gulfstream Drift at The Truman Annex in Key West

Photo gallery for A Gulfstream Drift at The Truman Annex in Key West

Outdoor dining
Private kitchen
Private kitchen
Private kitchen
Private kitchen

Reviews

9.8 out of 10
Exceptional
3 bedrooms3 bathroomsSleeps 7190.5 sq m

Popular amenities

  • Heated pool
  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Balcony

Explore the area

View map
Key West, FL
  • Place, Harry S. Truman Little White House
    ‪1 min walk‬
  • Place, Duval Street
    ‪5 min walk‬
  • Place, Mallory Square
    ‪6 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪14 min drive‬

Rooms & beds

3 bedrooms (sleeps 7)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 Single Bed and 1 Queen Bed

3 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Bathtub or shower · Toilet

Bathroom 3

Bathtub · Toilet · Shower only

Spaces

Kitchen
Balcony
Separate dining area

About this property

A Gulfstream Drift at The Truman Annex in Key West

Imagine yourself watching the sunset over the ocean from the huge penthouse balcony. This tropical retreat in Paradise has 2000 square feet of living space providing plenty of room for comfort and entertaining. The three large bedrooms have ocean views with en suite bathrooms in the master and king guest bedrooms. The third bedroom has a queen & one twin bed. The property is fully furnished and professionally decorated in a tropical theme complete with central AC, kitchenware, linens, TV, radio, cable internet with wifi, and a work desk in each bedroom. Other amenities are an elevator, covered private parking, nearby community pool and local professional management. This Harbour Place condo is conveniently located in prestigious Truman Annex in the Heart of Old Town, about 3 blocks from fabulous activities, shops and restaurants on Duval Street and about 1/4 mile from Fort Zachary Taylor State Park. This is Key West living at its finest for a vacation you will treasure.
Please note: This property has a 28 night minimum stay

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock

About the area

Key West

Located on the waterfront, this condo is in Old Town Key West, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. USCGC Ingham Maritime Museum and Florida Keys Eco - Discovery Center are also worth visiting. Discover the area's water adventures with jet skiing, scuba diving and snorkelling nearby, or enjoy the great outdoors with cycling.
Map
Key West, FL

What's nearby

  • Harry S. Truman Little White House - 1 min walk - 0.0 km
  • Duval Street - 5 min walk - 0.4 km
  • Key West Aquarium - 5 min walk - 0.4 km
  • Mallory Square - 6 min walk - 0.6 km
  • Ernest Hemingway Home and Museum - 12 min walk - 1.1 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 14 min drive

Restaurants

  • ‪Key Lime Pie Factory - ‬5 min walk
  • ‪Captain Tony's Saloon - ‬5 min walk
  • ‪Fogarty's and Flying Monkey's - ‬5 min walk
  • ‪The Bull & Whistle Bar - ‬5 min walk
  • ‪Caroline's Cafe - ‬8 min walk

Frequently asked questions

Does A Gulfstream Drift at The Truman Annex in Key West have a pool?

Yes, this property has a pool. Pool types include heated pools.

How much does it cost to stay at A Gulfstream Drift at The Truman Annex in Key West?

As of 28 Apr 2026, prices found for a 1-night stay for 2 adults at A Gulfstream Drift at The Truman Annex in Key West on 1 May 2026 start from AU$673, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is A Gulfstream Drift at The Truman Annex in Key West pet-friendly?

No, pets are not allowed at this property.

How much is parking at A Gulfstream Drift at The Truman Annex in Key West?

On-site parking is available at the property.

What time is check-in at A Gulfstream Drift at The Truman Annex in Key West?

Check-in begins at 4:00 PM.

What time is check-out at A Gulfstream Drift at The Truman Annex in Key West?

Checkout is at 10:00 AM.

Where is A Gulfstream Drift at The Truman Annex in Key West located?

Located in Old Town Key West, this condo building is within a 5-minute walk of Harry S. Truman Little White House and Duval Street. Florida Keys Beaches and Mallory Square are also within 10 minutes.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 27 out of 30 reviews
Rating 8 - Good. 3 out of 30 reviews
Rating 6 - Okay. 0 out of 30 reviews
Rating 4 - Poor. 0 out of 30 reviews
Rating 2 - Terrible. 0 out of 30 reviews

9.8/10

Cleanliness

8.0/10

Amenities

10/10

Property conditions & facilities

9.4/10

Check-in

9.0/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Lonnye

Liked: Cleanliness, amenities, property conditions & facilities, communication
Great place in a great location!
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

tiffany j.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The condo was really clean and well equipped. The location super walkable to everything we wanted to do. Would stay again!
Stayed 7 nights in May 2025
Verified

10/10 Excellent

Stacey K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Trip

Terrific location, great views, convenient to everything, and the apartment was beautiful!! Would stay again for sure!!
Stayed 7 nights in May 2025
Response from VrboOwner on 13 June 2025
Thanks for staying with Compass Realty!
Verified

10/10 Excellent

Kenneth W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Key West

Outstanding location and scenery from terrace. Loved the accommodations and could walk to night life and restaurants.
Stayed 7 nights in Apr 2023
Response from VrboOwner on 18 July 2023
Thanks for staying with Compass Realty!
From a partner site

10/10 Excellent

Jack H.

Great location

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Beautiful sunsets, walking to Mallory Square and Duval Street the location could not be better. Beautiful condo with everything needed to make your stay memorable. 5 stars
Stayed 7 nights in Jul 2024
Response from VrboOwner on 18 July 2024
Thanks for staying with Compass Realty!
Verified

10/10 Excellent

John T.

Liked: Cleanliness, check-in, location, listing accuracy

Didn’t want to leave

Liked everything about this place, the location and view is 1st rate.The only complaint I heard from our group of 6, was that we had to buy toilet paper and paper towels. Thought for the price they should be included. Having to tear down the linen and place in the laundry is also too much.
Stayed 7 nights in May 2025
Response from VrboOwner on 13 June 2025
Thanks for staying with Compass Realty! Next time just know that stripping the linens is not required, but appreciated!
Verified

8/10 Good

Maureen G.

Liked: Cleanliness, check-in, location, listing accuracy
Disliked: Communication

Great location

Comfortable condo, fabulous views, and w Some things did not make it They’re not walking distance to everywhere we wanted to go. Unfortunately communications with the realtor were less than ideal and parking became an unexpected issue.
Stayed 10 nights in Jul 2024
Response from VrboOwner on 8 Aug 2024
Thank you for taking the time to review your stay with us Maureen. We are sorry to read your experience with the parking wasn't a good one. That is why we note it in the contract that each unit comes with 1 parking spot and you are issued 1 parking pass. We hope you will come visit us again. Thank you for being our guest. here at Compass Realty.
Verified

10/10 Excellent

Stephanie G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful location beautiful views

Family of 6 adults! This property was very spacious and clean. The porch was our favorite spot! We were able to watch the commissioning and departure of USS Billings naval ship as well as the cruise ships. . Short walking distance to Duval Street and then back to the quiet of the Truman Annex. We are already planning a return trip and hoping this condo is available. I would rank this as a perfect spot!!! The only suggestion would be to make the pool location easier identifiable for quest. We had a wonderful time and enjoyed every minute of our trip.
Stayed 7 nights in Aug 2019
From a partner site

10/10 Excellent

Linda G.

Adult Family Vacation

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This was a fabulous rental. Space was enough to allow each family their own BR and bath. Location was awesome.The views from the deck were unbelievable. We would highly recommend.Initially the coffee pot did not work correctly but one visit to the office and it was immediately replaced!
Stayed 7 nights in May 2024
Response from VrboOwner on 23 May 2024
Thank you for this wonderful review, we are so glad you enjoyed your stay with us here at Compass Realty and hope to host you again next time you visit the island!
From a partner site

8/10 Good

Victor D.

Keys trip Oct 2020

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was somewhat dissatisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The property is beautiful and in a great location. Unit is in dire need of updating both the kitchen and baths as well as the furniture. Beds were very uncomfortable to sleep in.
From a partner site

10/10 Excellent

Rebecca C.

Amazing Sunsets Every Night!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We spent a week in this unit and couldn't have been happier. Well stocked kitchen, large bedrooms and an amazing balcony. Plenty of beach towels and even several beach chairs. We would stay here again in the future.
From a partner site

10/10 Excellent

Kenneth W.

Great place

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Three couples we have stayed here last two years. Just booked again for next year. This unit is the best. Large and plenty of room. Everything you will need is here. Outstanding view and location.
From a partner site

10/10 Excellent

P V B.

Key West in November

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Excellent!
From a partner site

10/10 Excellent

Scott M.

Perfect place.

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great location in the Truman Annex. Perfect for 6 adults. Beautiful sunsets.
From a partner site

10/10 Excellent

Paul & Trudy B.

Key West 2022

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had a fabulous time in our 3br, 3br unit. The staff at Compass Realty were very responsive and helpful. Overall we had a ball.
From a partner site

10/10 Excellent

Donna K.

Key West Adventure

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The unit was amazing and well appointed. Would rent again. The management company was excellent.
Verified

10/10 Excellent

Darr M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Highly recommend

This is the 2nd year in a row that I’ve stayed at this property and it’s an awesome condo
Stayed 7 nights in Jun 2022
From a partner site

10/10 Excellent

Janine M.

Everything you could want.

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This condo had everything we could want for a fabulous week in Key West. Plenty of towels, soap, tp, kitchen appliances, etc. A perfect sunset view every night. And best of all, a quiet oasis only a short walk from Duvall St.
From a partner site

10/10 Excellent

Brittany V.

Wonderful time

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: A beautiful property for our family vacation! Plenty of space and an amazing view of the sunset every night!
From a partner site

10/10 Excellent

A guest from Gibralter, MI

Fantastic stay at Truman Annex

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: My family and I stayed at the Gulfstream Drift property.Absolutely beautiful unit! Well maintained and has a great view of the Gulf! We will be coming back and asking for the same unit if possible. This is a must to stay if your here for a week or more.
From a partner site

10/10 Excellent

Brenda B.

Wonderful stay

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This condo was beautifully decorated, clean and in a great location. The best part though was the view! Calming views any time of day and gorgeous sunsets. We concluded that the balcony was a great spot in which to make plans but then we found we loved to simply linger right there!
Verified

10/10 Excellent

Cheryl H.

Liked: Cleanliness, location, listing accuracy

Relaxing week - 6 friends!

The view was spectacular! Fully stocked kitchen and bar area! Plenty of towels, including beach towels, 5 beach chairs and 2 umbrellas. Plenty of room for 3 couples! Definitely on our return property list!!
Stayed 7 nights in Apr 2022
Verified

8/10 Good

Karen B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Another day in paradise

This property was as advertised….beautiful spacious condo with all the amenities. The view from the balcony was breath taking! The only negative was the community pool. It was not well maintained…the worse thing was the dog fecees on the walk on the edge of the pool. It remained there for several days…we did not use the pool after that.
Stayed 7 nights in Oct 2021
Verified

10/10 Excellent

Rob M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Truman Annex

My family (6 people 16+) LOVED this property. It is very spacious, has a great view of the water, and is convenient to downtown Key West.
Stayed 7 nights in Jul 2021
Verified

10/10 Excellent

Darr M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great property

This condo was spectacular. I would highly recommend this property. Great location and amazing view and location
Stayed 7 nights in Jul 2021

About the host

Hosted by Compass Realty Vacation Rentals & Property Management

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