Condo

A Sunset Poolside at the Truman Annex in Key West

Photo gallery for A Sunset Poolside at the Truman Annex in Key West

A living room with a sofa, armchair, and TV. There's a door leading to a balcony with plants.
A water park with a slide, a water fountain, and palm trees at sunset.
A gated community entrance with a sign for Shipyard Condominiums, surrounded by palm trees and a clear blue sky.
A spacious living area with a wooden deck, a dining table with chairs, a blue sofa, and a kitchen in the background.
A living room with a beige sofa, a blue armchair, and a ceiling fan.

Reviews

8.6 out of 10
Excellent

Highlights

  • Room to spread out
    Enjoy a spacious layout that gives everyone more room to relax.
  • Onsite parking available
    Convenient and secure onsite parking, a rare amenity in the area.
  • At the center of it all
    Stay in a top rated central location, steps from the best attractions, dining, and entertainment.
  • Discover nearby landmarks
    Walk to Duval Street

Popular amenities

  • Balcony or patio
  • Shared communal pool
  • Air conditioning
  • Washer and dryer
  • Off-street parking available
  • Refrigerator

Explore the area

View in a map
Key West, FL
  • Place, Duval Street
    ‪6 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪8 min walk‬
  • Place, Fort Zachary Taylor Historic State Park
    ‪8 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪11 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 2

2 Twin Beds

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Spaces

Deck or patio

Add dates for prices

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  • Pool
  • Kitchen
  • Washer
  • Dryer
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About the neighborhood

Key West

Located in Key West, this condo is in the city center. Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. Ready for a night out? Consider The Key West Theater and Sloppy Joe's Bar.
Map
Key West, FL

What's nearby

  • Key West Naval Station - 3 min walk - 0.3 km
  • Duval Street - 6 min walk - 0.5 km
  • Ernest Hemingway Home and Museum - 8 min walk - 0.7 km
  • Fort Zachary Taylor Historic State Park - 8 min walk - 0.7 km
  • Florida Keys Beaches - 11 min walk - 0.9 km

Getting around

  • Key West Intl. Airport (EYW) - 19 min drive

Restaurants

  • ‪Margaritaville - ‬7 min walk
  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Blue Heaven - ‬8 min walk
  • ‪Moondog Cafe & Bakery - ‬8 min walk
  • ‪Bourbon Street Pub - ‬8 min walk

Frequently asked questions

Is A Sunset Poolside at the Truman Annex in Key West pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at A Sunset Poolside at the Truman Annex in Key West?

As of Nov 15, 2026, prices found for a 1-night stay for 2 adults at A Sunset Poolside at the Truman Annex in Key West on Dec 9, 2026 start from $441, 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.

How much is parking?

Onsite parking is available at the property.

What time is check-in at A Sunset Poolside at the Truman Annex in Key West?

Check-in begins at 4:00 PM.

What time is check-out at A Sunset Poolside at the Truman Annex in Key West?

Check-out is at 10:00 AM.

Where is A Sunset Poolside at the Truman Annex in Key West located?

Located in Old Town Key West, this condo building is within a 10-minute walk of Truman Waterfront Park, Duval Street, and Ernest Hemingway Home and Museum. Mallory Square and Florida Keys Beaches are also within 15 minutes.

Reviews

8.6

Excellent

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
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Rating 10 - Excellent. 21 out of 37 reviews
Rating 8 - Good. 9 out of 37 reviews
Rating 6 - Okay. 5 out of 37 reviews
Rating 4 - Poor. 1 out of 37 reviews
Rating 2 - Terrible. 1 out of 37 reviews

9.4/10

Cleanliness

8.6/10

Check-in

9.8/10

Communication

10/10

Location

9.4/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

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

Winter Vacation

Great location. Had an issue with no water upon checking in, but was resolved quickly by maintenance and management. Would stay again!!
Stayed 7 nights in Dec 2022
Response from VrboOwner on Feb 1, 2023
Thank you for sharing a review of your recent experience Amy. Our team here at Compass Realty is committed to providing high-quality guest service, and we’re thrilled to hear that we made a good impression on you. We look forward to welcoming you again! Thank you for being our guest! I am glad the water issue was resolved so quickly!
Verified review

10/10 Excellent

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

May 2023

Great location, walking distance to everything. Condo well stocked.
Stayed 14 nights in Apr 2023
Response from VrboOwner on May 22, 2023
Thank you for sharing a review of your recent experience Steward. Our team here at Compass Realty is committed to providing high-quality guest service, and we’re thrilled to hear that we made a good impression on you. We look forward to welcoming you again ! Thank you for being our guest!
From a partner site

6/10 Okay

Vacation

Rating Details: The property manager was very helpful. The vacation rental was very clean. 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: Acceptable
Response from VrboOwner on Jul 19, 2023
Thanks for staying with Compass Realty!
From a partner site

10/10 Excellent

Tutcher Review of Unit 156

Rating Details: The property manager was very helpful. The vacation rental was very clean. I was more than 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 couple of minor issues but Compass Corrected them immediately, otherwise we had a great time.
Response from VrboOwner on Jul 18, 2023
William 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

10/10 Excellent

Very Good

Rating Details: The property manager was very helpful. The vacation rental was very clean. 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: The condo was conveniently located near the pool. Everything was clean and in working order. The Compass office nearby was a plus.I would suggest that the owner supply comfortable chairs on the front and back deck. A bit of gardening and cleanup in back area would be nice.
Verified review

10/10 Excellent

Liked: Cleanliness, communication, location, listing accuracy

Sweet spot

This is a great place for a couple with or without one or two children. It is not great for 2 or more friends as one room has twin beds. And there is only a small sofa and bar chairs for indoor seating. There is a nice pool with lots of chairs one minute away and Duval Street is nearby.
Stayed 7 nights in Mar 2022
Response from VrboOwner on Apr 18, 2022
Thank you for the great feedback!! We hope you'll come and stay again! -Compass Realty
From a partner site

10/10 Excellent

Review

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: Vacation Experience was excellent. Great location, condo laid out great for a two couple stay, always clean and well kept. We have stayed in this condo for many years and love it. Only downside is a frustrating Roku TV to get it to work, but this is not that important to us.
Verified review

6/10 Okay

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

Great location near the pool.

Enjoyed our stay. The unit is as advertised.Had a couple minor issues that were quickly resolved. There are a few deferred maintenance items that should be addressed like the broken microwave handle, broken cabinet doors, loose headboard on the queen bed (makes a loud noise), slow draining shower, needed paint. Having said that, I would gladly stay in this unit again. Property management team is fantastic.
Stayed 7 nights in Oct 2024
Response from VrboOwner on Nov 8, 2024
Thank you for bringing these concerns to our attention Jason. We regret that your experience did not meet your expectations and have shared your feedback with our team. We will address the issues you have pointed out. Just know for the future that a quick call to the office would have sent maintenance to fix all issues besides painting. Please reach out to us for your next stay so we can make sure to find you the perfect unit! Thank you for being our guest at Compass Realty!
From a partner site

6/10 Okay

A Sunset Poolside

Rating Details: The property manager was very helpful. The vacation rental was clean. I was very happy with the location. I was satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Overall good-1 bath door did not lock, the other bath shower did not drain properly and a shelf fell out in medicine cabinet. Did not break, but the shelf support did not hold. We did not stay inside the unit except at night to sleep because we enjoy everything about Key West outside. We also love the locality of Truman Annex and especially that this unit was just steps from the pool.
From a partner site

10/10 Excellent

Review

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: Vacation Experience was excellent. Great location, condo laid out great for a two couple stay, always clean and well kept. We have stayed in this condo for many years and love it. Only downside is a frustrating Roku TV to get it to work, but this is not that important to us.
Verified review

10/10 Excellent

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

NA

Love Truman Annex
Stayed 7 nights in Apr 2024
Response from VrboOwner on May 6, 2024
Thanks for staying with Compass Realty!
From a partner site

8/10 Good

gREAT rIDE

Rating Details: The property manager was very helpful. The vacation rental was very clean. I was more than happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: eVERYTHING WAS GREAT
From a partner site

8/10 Good

Key West February Stay

Rating Details: The property manager was very helpful. The vacation rental was very clean. 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: The unit we rented was small, but perfect for two couples. It was well supplied with everything we needed. The bathroom attached to the front bedroom did have an odor, possibly the plumbing. The shower in the second bathroom doesn’t drain right. The thermostat kept “jumping” to 85 degrees. We turned it down to 65 and, after a while, it would jump up again. It was a little cool the week we were there so it wasn’t too big a deal, but if had been a hot week, it would have been miserable.
From a partner site

10/10 Excellent

Very Comfortable!

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: Very clean and nice place. All on one level which was nice. Although we didn't use the pool, its right out the front door.
From a partner site

10/10 Excellent

Wonderful experience

Rating Details: The property manager was more than helpful. The vacation rental was very clean. 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 entire experience from finding the right place to stay during the KWLC that fit three people, to easy check in/walkability/clean/well appointed, all of that. Highly recommend.
From a partner site

10/10 Excellent

Poolside Paradise

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 Sunset Poolside condo was in the perfect location in Truman Annex. Well equipped compact space with a beautiful tropical view of the pool from the front porch and the lush gardens from the back patio. K-cup and drip coffee. Very close to Ft Zachary or the Truman Waterfront Park to see spectacular sunsets and cruise ships arriving or departing. Easy walk to Duval for all of our favorite restaurants. Had a little trouble finding the rental office and the unit at first. Should have paid more attention to the rental office’s directions instead of the driver that thought he knew where to go. Very clean and exactly as pictured. Pool right outside the unit was a great extension of the space. Will definitely be back!
From a partner site

6/10 Okay

Beautiful Truman Annex

Rating Details: The property manager was more than helpful. The vacation rental was very dirty. 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: Beautiful location and easy to navigate !
Stayed 8 nights in May 2021
From a partner site

10/10 Excellent

Best 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: Love this location - so close to everything! Good contact with the management co regarding arrival and departure. Condo was very clean. Kitchen is a bit small - one person at a time.
From a partner site

10/10 Excellent

Holiday recovery.

Rating Details: The property manager was adequately 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: Perfect get away after the holiday.
From a partner site

10/10 Excellent

7 nights of a much needed vacation

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: Compass Realty was wonderful to deal with. They responded to any questions quickly and provided all necessary information for the property.It was my husband, myself and another couple. The condo is not very large but we weren't spending much time there so it was perfect. The pool was right out the front door. It is very peaceful there. Unit was clean, kitchen seemed well equipped. We did not cook at all, too many good restaurants to go to and I was on vacation.
Stayed 7 nights in May 2021
From a partner site

2/10 Terrible

Needs attention.

Rating Details: The property manager was more than helpful. The vacation rental was clean. I was more than happy with the location. I was very dissatisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: We have rented 6 times in the Truman Annex, three times in the Shipyard. Up until now, very good experiences but would not rent this unit again. First of all, the photos of the unit are no longer accurate. Apparently there has been a change of ownership or a decision to remodel but the two sofas, lamps, etc. are no longer there. The unit now contains one large new but very uncomfortable sofa and one table lamp. A new large TV is mounted on the wall.The one sofa provides seating for two people. No other seating except for high kitchen stools or bringing in outside dining chairs. Fortunately, there were only two of us. Would be very uncomfortable for two couples or with children. As a previous reviewer noted, the dishwasher is only half size and comes out of the cabinet when opened. The smoke detector in the bedroom is missing. The unit needs attention -- some comfortable chairs, better lighting, better linens, some new kitchen supplies.
From a partner site

6/10 Okay

Sunset Poolside

Rating Details: The property manager was very helpful. The vacation rental was clean. 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: Our 4th time leasing this condo and was not up to expectations.
From a partner site

10/10 Excellent

Key West winter get away

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: Over all a wonderful condo with good location and clean! Freshly decorated. Truly enjoyable!
From a partner site

4/10 Poor

A Sunset Poolside was substandard

Rating Details: The property manager was more than helpful. The vacation rental was very clean. I was very happy with the location. I was very dissatisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: The attached picture is entirely false. Significant pieces of furniture had been removed and not replaced. We had to carry the patio chairs in and out to have sufficent seating. We had inadequate accommodation for our clothes in one bedroom, as a chest had been removed. The kitchen fittings were barely minimal, including a partly broken dishwasher. Vacuum cleaner also broken and one smoke alarm missing. If owners are required to meet certain standards, this one did not. If there are no standards, there should be.
From a partner site

8/10 Good

Good stay

Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great location next to the pool! General condition of the unit is starting to show its' age. Dishwasher isn't secured and the flooring is worn. Otherwise though, great e
Stayed 7 nights in Apr 2022
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