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Tropical Breezes at The Truman Annex in Key West

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Pool - Tropical Breezes at The Truman Annex in Key West (Key West)
TV - Tropical Breezes at The Truman Annex in Key West (Key West)
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Property grounds - Tropical Breezes at The Truman Annex in Key West (Key West)
Exterior - Tropical Breezes at The Truman Annex in Key West (Key West)
In the heart of Key West's old town, Shipyard Condominiums offers a comfortable retreat with central air conditioning and off-street parking. With pool access, washer/dryer, and fully equipped kitchens with pots/pans, linens/towels provided for your convenience.

Reviews

9.0 out of 10
Wonderful

Entire condo

2 bedrooms1 bathroomSleeps 463 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Parking available

Add dates for prices

About this property

Entire place

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

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 29 nights/30 days, except for February, which is 28 nights!!!

Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Communal pool

Internet

  • Available in the condo: Free WiFi

Parking and transport

  • Parking on site

Kitchen

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

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Bathtub or shower
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • TV with cable/satellite channels

Outdoor areas

  • Balcony

Laundry

  • Laundry facilities
  • Washer/dryer

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Single level property
  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city centre
  • Near the sea

Things to do

  • Ecotours nearby
  • Fishing nearby
  • Jet skiing nearby
  • Scuba diving 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)
  • Deadbolt lock

General

  • Gated community
  • Unit size: 680 square feet

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Property grounds
Craig & Cindy Key West Truman Annex Shipyard Condo with balcony at Mile Marker 0
  • Pool
  • Kitchen
  • Washing machine
  • Dryer
10.0 out of 10, Exceptional, 17 reviews
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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
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

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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 deadlock
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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

Property is also known as

Tropical Breezes in the Truman Annex
Tropical Breezes @ the Truman Annex Key West
Tropical Breezes @ the Truman Annex Private vacation home
20% Off Summer Special Tropical Breezes @ the Truman Annex
2698-193344

About the area

Located near the beach, this condo is in Old Town Key West, a neighbourhood in Key West. 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. Visit our Key West travel guide
View more Condo rentals in Key West
Map
Key West, FL

What's nearby

  • Duval Street featuring signage
    Duval Street
    6 min walk - 0.5 km
  • Ernest Hemingway Home and Museum featuring heritage elements and a house
    Ernest Hemingway Home and Museum
    6 min walk - 0.5 km
  • Fort Zachary Taylor Historic State Park showing military items, heritage elements and interior views
    Fort Zachary Taylor Historic State Park
    8 min walk - 0.7 km
  • Mallory Square which includes a square or plaza, outdoor art and signage
    Mallory Square
    11 min walk - 1.0 km
  • Florida Keys National Marine Sanctuary
    5 min walk - 0.4 km

Getting around

  • Key West, FL (EYW-Key West Intl.)
    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 is parking at Tropical Breezes at The Truman Annex in Key West?

On-site 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?

Checkout 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. Fort Zachary Taylor Historic State Park and Mallory Square are also within 15 minutes.

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Tropical Breezes at The Truman Annex in Key West Reviews

Reviews

Wonderful

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens 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

Cleanliness

9.8

Location

Reviews

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

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

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
This review comes from a trusted partner site and has not been verified.

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

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

10/10 Excellent

angella p.

Amazing

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

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
This review comes from a trusted partner site and has not been verified.

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.
This review comes from a trusted partner site and has not been verified.

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.
This review comes from a trusted partner site and has not been verified.

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
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Margie A., Goodlettsville,TN

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.
This review comes from a trusted partner site and has not been verified.

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
This review comes from a trusted partner site and has not been verified.

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.
This review comes from a trusted partner site and has not been verified.

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.
This review comes from a trusted partner site and has not been verified.

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.
This review comes from a trusted partner site and has not been verified.

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!
This review comes from a trusted partner site and has not been verified.

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.
This review comes from a trusted partner site and has not been verified.

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.

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

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

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

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

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

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

10/10 Excellent

Terry B., canton

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