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A Gulfstream Drift at The Truman Annex in Key West

Condo near Duval Street in Key West

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

A balcony with two lounge chairs, a view of the ocean, and a white building in the background.
A pathway lined with palm trees and tropical plants, leading to a marina with sailboats.
A multi-story hotel with balconies, palm trees, and a white fence.
A spacious living room with a large window, a dining area, and a separate kitchen.
A rectangular pool with blue lounge chairs and palm trees around it.

Reviews

9.8 out of 10
Exceptional

Entire condo

3 bedrooms3 bathroomsSleeps 72050 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

Explore the area

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

Room options

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Exterior

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9.0 out of 10, Wonderful, 1,845 reviews
$192 nightly
The price is $216
Aug 2 - Aug 3
Total with taxes and fees
Hilton Key West Resort & Marina

About the neighborhood

Key West

Seaside stay .Within a 10-minute walk of this Old Town Key West condo, you'll find Duval Street and Florida Keys Beaches. Also, Mallory Square is within half a mile (1 km) and Southernmost Point is within 2 miles (3 km).
View more Condo Rentals in Key WestOpens in a new window

What's nearby

  • Harry S. Truman Little White House - 1 min walk - 0.0 miles
  • Key West Naval Station - 3 min walk - 0.2 miles
  • Duval Street - 5 min walk - 0.3 miles
  • Mallory Square - 5 min walk - 0.3 miles
  • Ernest Hemingway Home and Museum - 12 min walk - 0.7 miles

Getting around

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

Restaurants

  • ‪The Bull & Whistle Bar - ‬5 min walk
  • ‪Key Lime Pie Factory - ‬5 min walk
  • ‪Captain Tony's Saloon - ‬5 min walk
  • ‪Fogarty's and Flying Monkey's - ‬5 min walk
  • ‪Cuban Coffee Queen - ‬4 min walk

About this property

Entire place

You'll have the entire condo to yourself and will only share it with other guests in your party.

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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Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Communal pool
  • Heated pool

Internet

  • Available in the condo: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 3 private bathrooms
  • Bathtub
  • Bathtub or shower
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Living room
  • Separate dining area

Entertainment

  • TV with cable/satellite channels

Outdoor areas

  • Balcony

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Elevator
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center
  • Near the marina
  • Near the ocean
  • On the waterfront

Things to do

  • Heated pool
  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • Unit size: 2,050 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

No events allowed

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
Onsite 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 there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a fire extinguisher, a smoke detector, and a deadbolt lock in each accommodation.

Property is also known as

2698-193298

Frequently asked questions

How close is A Gulfstream Drift at The Truman Annex in Key West to the airport?

This condo is 4.1 mi (14-min drive) away from the Key West Intl. Airport (EYW) airport, the closest popular airport to the property.

Does A Gulfstream Drift at The Truman Annex in Key West have an airport shuttle?

Airport shuttle services are not available at this condo.

How close is A Gulfstream Drift at The Truman Annex in Key West to the beach?

This condo is a short 9-minute walk from Florida Keys Beaches and 1.1 mi (9-min drive) from South Beach. Don't forget your sunscreen!

Does A Gulfstream Drift at The Truman Annex in Key West offer free breakfast?

This condo does not offer free breakfast.

Is there a casino at A Gulfstream Drift at The Truman Annex in Key West?

No, there is no casino at this condo.

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

Check-in begins at 4:00 PM.

Is there free parking at A Gulfstream Drift at The Truman Annex in Key West?

Free parking is not available at this condo.

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

Yes, there's a heated pool.

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

There are no spa services available at this condo.

How close is A Gulfstream Drift at The Truman Annex in Key West to downtown Key West?

This condo is 0.3 mi away from Key West.

A Gulfstream Drift at The Truman Annex in Key West Reviews

Reviews

9.8

Exceptional

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

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
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
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
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
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
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
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

Verified traveler

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

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