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Tropical Breezes at The Truman Annex in Key West

Photo gallery for Tropical Breezes at The Truman Annex in Key West

SY294-05
SY294-04
SY294-06
SY294-13
SY294-10

Reviews

9.0 out of 10
Wonderful
2 bedrooms1 bathroomSleeps 4680 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Parking available

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 2

2 Twin Beds

1 bathroom

Bathroom 1

Bathtub or shower · Toilet

Spaces

Kitchen
Balcony

About this property

Tropical Breezes at The Truman Annex in Key West

Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The condos are located 2 blocks from Duval Street and all the Old Town Key West attractions. The properties are also ¼ mile from Fort Zachary Taylor State Park. The property is outfitted with washer/dryer, pots/pans, towels, linens, have central air conditioning, off street parking, and pool access. This Shipyard home is a single level condominium on the 2nd floor with balconies. This property also has an awning for coverage from the sun.
Please note: This property is monthly rental - the minimum rental period is 28 nights
Our prices include all fees. No hidden fees.

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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
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 deadbolt lock

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. USCGC Ingham Maritime Museum and Mel Fisher Maritime Museum are also worth visiting. Discover the area's water adventures with jet skiing, scuba diving, and fishing nearby, or enjoy the great outdoors with ecotours.
Map
Key West, FL

What's nearby

  • Florida Keys National Marine Sanctuary - 5 min walk - 0.4 km
  • Duval Street - 6 min walk - 0.5 km
  • Ernest Hemingway Home and Museum - 6 min walk - 0.5 km
  • Fort Zachary Taylor Historic State Park - 8 min walk - 0.7 km
  • Mallory Square - 11 min walk - 1.0 km

Getting around

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

Restaurants

  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Willie T's - ‬6 min walk
  • ‪Mangoes Restaurant - ‬7 min walk
  • ‪Blue Heaven - ‬8 min walk
  • ‪Rams Head Southernmost - ‬7 min walk

Frequently asked questions

Is Tropical Breezes 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 Tropical Breezes at The Truman Annex in Key West?

As of Apr 4, 2026, prices found for a 1-night stay for 2 adults at Tropical Breezes at The Truman Annex in Key West on Apr 25, 2026 start from $176, 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 Tropical Breezes at The Truman Annex in Key West?

Check-in begins at 4:00 PM.

What time is check-out at Tropical Breezes at The Truman Annex in Key West?

Check-out is at 10:00 AM.

Where is Tropical Breezes 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. Florida Keys Beaches and Fort Zachary Taylor Historic State Park are also within 15 minutes.

Reviews

9.0

Wonderful

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 17 out of 26 reviews
Rating 8 - Good. 6 out of 26 reviews
Rating 6 - Okay. 2 out of 26 reviews
Rating 4 - Poor. 0 out of 26 reviews
Rating 2 - Terrible. 1 out of 26 reviews

9.2/10

Cleanliness

9.0/10

Check-in

9.2/10

Communication

10/10

Location

9.4/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Jami P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The condo was great for our stay. The beds were comfortable and the kitchen was well equipped.
Stayed 7 nights in Nov 2025
Verified

8/10 Good

Bill V.

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

Great place

Perfect location. Quiet but close to everything. Clean, safe. Would stay again.
Stayed 7 nights in Feb 2023
Verified

10/10 Excellent

angella p.

Amazing

Amazing. Enjoy so much!!!
Stayed 7 nights in Apr 2018
Verified

10/10 Excellent

Lili C.

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

Clean, quiet, comfortable & convenient

The apartment is conveniently located in the Truman Annex area of Key West. Apt looks just like pics. Furniture & decoration is a little dated but overall it was very clean and comfortable and had all the basics to make for an easy family vacation. Keyless entry made it easy to check in and when we had a slight issue with missing pool gate keys the realty office is a quick 5min walk away. Quiet area but only a few minutes to all the restaurants and shops of Duval etc.
Stayed 14 nights in Dec 2024
From a partner site

10/10 Excellent

Laurie S.

Key West Gem

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: Condo was a great location, near all the places in Key West! Also close enough to bike to the State Park which has a nice beach. One recommendation would be to have a key pad so we didn’t have to take a cab to the office to get the key upon arrival and to turn it in upon departure.
Verified

8/10 Good

Elizabeth J.

Liked: Communication, location, listing accuracy
Disliked: Cleanliness

Quick get away

Upon our arrival we were met with a yet to be cleaned unit. The management did respond quickly and dispatched a cleaning crew right away. Ongoing construction in the unit below our rental was completely annoying.
Stayed 7 nights in Mar 2025
Verified

10/10 Excellent

Lori B.

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

April 2025

The condo was set up perfect. Very nice set up with a back deck and a front deck. Beach chairs we were able to use. So many extras. Washer, Dryer, Dishwasher. The kitchen was well equipped. Pretty much had everything we needed for the meals we cooked in the condo.The roof was being replaced while we were there which was very noisy. I wished the management had extended the courtesy of notifying us the roof was being replaced during our vacation. It was never mentioned.
Stayed 7 nights in Apr 2025
From a partner site

10/10 Excellent

Bm

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 nice and easy process
From a partner site

8/10 Good

Keith F.

Keith & Diane’s stay

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: Condo was clean. Loved the balconies and the conveniences of the washer and dryer in the unit. Location of the Truman Annex is perfect for our stays..able to walk everywhere we wanted to go. Stairway up to 2nd floor is very difficult to navigate while carrying luggage &/or groceries. Process of checking in & out with Compass Realty could’ve been smoother...we had no idea the procedure for obtaining a parking pass had changed. About a month prior to leaving home, we had voiced our concern to an agent about the need for assistance with our bags when we arrive, (either a person or baggage cart), and were told assistance could be arranged. Upon check in, there happened to be an agent in the office who informed me those arrangements couldn’t be done, nor are they able to. Despite the fact we have loved staying at the Truman Annex Shipyard for a number of years, we’re no longer able to stay in 2nd floor units, and hope that perhaps a first floor condo will be available in the future.
From a partner site

6/10 Okay

Charles L.

A little too far away...

Rating Details: The property manager was more than helpful. The vacation rental was spotless. I was very unhappy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: Truman Annex has some great units and features. Tropical Breezes is a nice unit but a little dated. It’s real problem is that it is located about as far away from everything at the Annex as you can be. It also overlooked a local neighborhood which was somewhat noisy.
Stayed 7 nights in Aug 2021
From a partner site

10/10 Excellent

Margie A.

May in Key West

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: Really enjoyed this condo on the 2nd floor.This unit was well stocked with everything you need & very well taken care of. It was in a great location to everything & only a short walk to the pool. Rented bikes for the week which is a fantastic way to see Key West. The only downside was if you don't get to the pool early you can't get a chair. Pool is not big enough to accommodate lots of people. Other than that we loved it here.
From a partner site

10/10 Excellent

Christy C.

Loved this condo!

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: Enjoyed our stay at Tropical Breezes so much! Location, location, location! It was very quiet, got wonderful sleep, beds were super comfy. Enjoyed my tea and coffee on the balcony each morning, biked all over the island, soaked up lots of sun and fun, watched sunsets most nights from Truman waterfront park. This was our first time to Key West (myself and two daughters) and I can't wait to come back! Upon arrival, coffee maker and blowdryer didn't work, they promptly delivered a new one of each. I would definitely stay here again and highly recommend.
From a partner site

10/10 Excellent

Jack M.

First of hopefully many Key West experiences in 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: Great location at a fair and reasonable price-The management team was gracious and responded promptly to any questions we had as first time guests-We will definitely be back
From a partner site

10/10 Excellent

Timothy W.

Easy walk to town

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: Clean, well appointed property with an easy walk to town and points of interest. On the small side, but perfect for two college buddies having a reunion. Management provided prompt service when our coffee maker broke. Overall I’d highly recommend.
From a partner site

10/10 Excellent

Greg R.

Fantastic Week!

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 have been coming to KW for over 20 years and this is our first time staying in the Truman annex thru your company. We loved our condo and your company did a fantastic job. We will be using your services again. Thanks for a great week!
From a partner site

2/10 Terrible

Kristen R.

Don't Trust Compass to HOLD your reservation!

Rating Details: The property manager was somewhat unhelpful. The vacation rental was clean. I was very unhappy 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 booked a year in advance and found out a week before our arrival that Compass had moved us from a 2 bath to a 1 bath unit. The new unit was nothing like what I booked as far as furnishings, bed configuration, and it had 1 television vs 3 in the unit I also backed up to a busy street, and had no outdoor dining space. The unit I booked overlooked the pool and had a nice outdoor dining table for 4.This was a miserable 1 month stay. Never again will I use Compass.
From a partner site

6/10 Okay

Brenda W.

Disappointed

Rating Details: The property manager was more than helpful. The vacation rental was somewhat dirty. I was more than happy with the location. I was satisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: This was our 5th stay in the Shipyards (2nd time in this unit) and you really can’t beat the location. We enjoyed spending time at the pool, walking to nearby beaches, dining on seafood, sipping cocktails and watching sunsets. This unit is rather dark and grungy and in need of some love and attention. It was not thoroughly cleaned before our arrival (multiple issues including broken glass in the cupboard, unusable frypan, and the previous renters coffee grounds still in the pot). Compass was responsive (offered another cleaning or credit and quickly dropped off missing lightbulbs) but it was a poor start to our 2 weeks in paradise. We made the best of it and will likely return to the Truman Annex next year but will look for a lower unit and hopefully more updated and cleaner. We also found renting through Compass very inconvenient as they now close their office on Saturdays and you can no longer leave your luggage there while you wait until the 4pm check in.
From a partner site

10/10 Excellent

Paul M.

SY294 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: Great property, great location. We had a problem with the air condition at 7 p.m. compass realty has an overnight help number and they responded within in a hour and had it fixed in two hours. Great service.
Verified

8/10 Good

Bob C.

Liked: Cleanliness, check-in, communication, location
Disliked: Listing accuracy

Verbo is a rip off

We love Key West. Been here many times. ALWAYS call the local real estate offices. Don’t pay the Verbo adders
Stayed 7 nights in May 2022
Verified

8/10 Good

Matt S.

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

Great stay at the adorable Truman Annex

Perfect location to walk everywhere. Nice to have a condo with more room and pool rather than a hotel room with a family of 4 for the week. Wish we had a second bathroom, but the place was great. Would definitely book in Truman Annex again and recommend. Walls are thin so we could hear the people downstairs and they could hear us (man downstairs was unkind about that, but hopefully enjoyed his vacation nonetheless since we were not at the condo for most of the day every day).
Stayed 7 nights in Apr 2022
Verified

8/10 Good

Mike S.

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

Relaxing Stay in Key West

Nice location for taking in everything Old Town Key West has to offer.
Stayed 8 nights in Dec 2021
Verified

10/10 Excellent

Colton L.

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

Great experience

The property is very clean and well-kept. Checking in and out were very easy. The location is great for all entertainment. I would certainly stay again!
Stayed 7 nights in Oct 2021
Verified

10/10 Excellent

Shaun M.

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

Amazing location

Beautiful grounds, close to everything. Would stay again. Rent a bike a got to the Fort Taylor beach or walk over to Duvall. AC was cold to beat the heat. Wish my stay had been longer.
Stayed 7 nights in Jul 2021
Verified

10/10 Excellent

PETE M.

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

Well worth it!

The neighborhood, the place itself, everything was perfect! My wife and two kids had a great time exploring all Key West had to offer. The room was a perfect spot to return to each night. The pool was a nice addition as well.
Stayed 7 nights in Jun 2021
Verified

10/10 Excellent

Terry B.

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

Just Awesome

Renting from compass realty is a must whenever staying in Key West. The condo was well cleaned and up to date. They do their best to try and get you in early if you happen to arrive early. Their locations of property put you right where you wanna be.
Stayed 7 nights in May 2021

About the host

Hosted by Compass Realty Vacation Rentals & Property Management

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