Verified
10/10 Excellent
Timothy S.
17 November 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Timothy S.
Stayed 14 nights in Oct 2025
Condo
Island Breezes at the Truman Annex in Key West
Photo gallery for Island Breezes at the Truman Annex in Key West
Reviews
9.69.6 out of 10
Exceptional
2 bedrooms1 bathroomSleeps 4
Popular amenities
- Heated pool
- Onsite parking available
- Kitchen
- Washing machine
- Air-conditioning
- Balcony
Explore the area
Key West, FL
- Duval StreetPlace, Duval Street6 min walk
- Ernest Hemingway Home and MuseumPlace, Ernest Hemingway Home and Museum6 min walk
- Fort Zachary Taylor Historic State ParkPlace, Fort Zachary Taylor Historic State Park8 min walk
- Key West, FL (EYW-Key West Intl.)Airport, Key West, FL (EYW-Key West Intl.)13 min drive
Rooms & beds
2 bedrooms (sleeps 4)
Bedroom 1
1 Queen Bed
Bedroom 2
2 Single Beds
1 bathroom
Bathroom 1
Bathtub or shower
Spaces
Kitchen
Balcony
Separate dining area
About this property
Island Breezes at the Truman Annex in Key West
WEEKLY RENTAL - This property has the ability to be rented weekly.
This charming second floor condominium features two bedrooms, and one full bath with views of the Truman Waterfront Park and the Florida Keys Eco Discovery Center.... | Located in the Shipyard within the award wining gated community of the Truman Annex, includes a community pool, off street parking and all of the amenities of home, including a laundry center. | The Truman Annex is conveniently located 2 blocks from Duval Street and Fort Zachary Taylor State Park and Beach and all of the Old Town Key West attractions.
Please note: This property can be rented for a minimum of 7 nights.
This charming second floor condominium features two bedrooms, and one full bath with views of the Truman Waterfront Park and the Florida Keys Eco Discovery Center.... | Located in the Shipyard within the award wining gated community of the Truman Annex, includes a community pool, off street parking and all of the amenities of home, including a laundry center. | The Truman Annex is conveniently located 2 blocks from Duval Street and Fort Zachary Taylor State Park and Beach and all of the Old Town Key West attractions.
Please note: This property can be rented for a minimum of 7 nights.
Add dates for prices
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House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets 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
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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
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 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. Jet skiing and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and cycling nearby.
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, FL (EYW-Key West Intl.) - 19 min drive
Restaurants
- Green Parrot Bar - 4 min walk
- Mangoes Restaurant - 7 min walk
- Blue Heaven - 8 min walk
- Rams Head Southernmost - 7 min walk
- Moondog Cafe & Bakery - 8 min walk
Frequently asked questions
Does Island Breezes 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 Island Breezes at the Truman Annex in Key West?
As of 14 April 2026, prices found for a 1-night stay for 2 adults at Island Breezes at the Truman Annex in Key West on 13 June 2026 start from NZ$777, 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 Island Breezes at the Truman Annex in Key West pet-friendly?
No, pets are not allowed at this property.
How much is parking at Island Breezes at the Truman Annex in Key West?
On-site parking is available at the property.
What time is check-in at Island Breezes at the Truman Annex in Key West?
Check-in begins at 4:00 PM.
What time is check-out at Island Breezes at the Truman Annex in Key West?
Checkout is at 10:00 AM.
Where is Island 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
9.6
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new windowRating 10 - Excellent. 20 out of 24 reviews
10 - Excellent
20
Rating 8 - Good. 3 out of 24 reviews
8 - Good
3
Rating 6 - Okay. 1 out of 24 reviews
6 - Okay
1
Rating 4 - Poor. 0 out of 24 reviews
4 - Poor
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Rating 2 - Terrible. 0 out of 24 reviews
2 - Terrible
0
9.8/10
Cleanliness
9.2/10
Check-in
9.4/10
Communication
9.6/10
Location
9.6/10
Listing accuracy
Reviews
Response from VrboOwner on 17 November 2025
Timothy 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!
Verified
10/10 Excellent
Andrew B.
17 December 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Place to Sleep
Truman Annex is a great location. Nice shared community pool. Blocks from the heart of Duval St. and a short walk to Fort Zachary Taylor beach.
Andrew B.
Stayed 7 nights in Dec 2022
Response from VrboOwner on 9 February 2023
Thanks for staying with Compass Realty!
Verified
10/10 Excellent
robert s.
19 May 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great
No problem
robert s.
Stayed 10 nights in May 2025
Response from VrboOwner on 4 June 2025
Thanks for staying with Compass Realty!
From a partner site
10/10 Excellent
Lora C.
25 April 2023
GREAT PLACE TO 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:
THE VACATION RENTAL WAS PERFECT. CLEAN, GREAT LOCATION, AND LOVE THE 2 BALCONIES.
Lora C.
Stayed 7 nights in Apr 2023
Response from VrboOwner on 12 July 2023
Lora 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
Laura W.
18 May 2022
Great 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:
We enjoyed our week's stay in Key West 12/10-12/17/21. The unit in Truman Annex was nice, clean, comfortable and safe.
Laura W.
From a partner site
10/10 Excellent
Deborah H.
31 January 2023
Island Breezes Stay
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:
Great location, good stay; 1 suggestion would be to put "black-out" curtains on main bedroom patio door windows to eliminate all the lights from the nearby tower and soccer field for better sleeping.
Deborah H.
Response from VrboOwner on 19 July 2023
Thanks for staying with Compass Realty!
From a partner site
10/10 Excellent
Jim C.
10 May 2024
Songwriters Festival Sanctuary
Rating Details:
The property manager was very 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:
Great experience. Quiet, well appointed, small condo in great area, close to all venues....walk to all spots. Great air conditioning, kuerig, stocked kitchen. Upper floor, relatively steep stairs only mentioned for elderly or small children. Great communication and instructions from Compass Realty
Jim C.
Stayed 7 nights in Apr 2024
Response from VrboOwner on 23 May 2024
Jim 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
Joyce K.
14 June 2022
Excellent Choice
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 was the perfect place for our family and an excellent location where we could walk everywhere. The unit was as advertised and as always we would have loved to stay longer. The Truman Annex is well maintained with lovely landscaping, quiet evenings, a great pool to enjoy and a safe environment. We were able to park our vehicle and walk everywhere which makes it a great spot to stay. The unit was clean and provided everything we needed throughout our stay. We enjoyed sitting on both of the porches throughout the day. The people in the office are friendly and helpful and answered all my questions. I highly recommend staying in the Truman Annex and Island Breezes.
Joyce K.
Verified
6/10 Okay
karen b.
28 February 2023
Liked: Check-in, communication, location, listing accuracy
Needs updating but GREAT location
I love the Shipyard at Truman Annex. You would think the owners would keep the units updated for what these units charge. The toilet seat needs to be replaced (it's all scratched and gross). The bath towels are thin and worn out and need to be replaced. The sofa in the living room is not comfortable. It has wood under the cushion which is not helping. Areas in the kitchen and throughout could use some painting. One night a lot of worm-like bugs came into the unit (I think thru walls and piping) which I contributed to the outside walkways being power washed that day because the bugs were gone the next day. But, it was annoying having to kill a lot of bugs that completely grossed me out. The positives are the queen bed was very comfortable and the location was great! I am a cleaning and germaphobic nut, so I did clean myself and kept the place as clean as possible during our 2 week stay.
karen b.
Stayed 14 nights in Feb 2023
Response from VrboOwner on 12 July 2023
Thanks for the review Karen! The toilet seat and towels have been replaced since this review. Please stay with us again at Compass Realty!
From a partner site
10/10 Excellent
Timothy F.
26 November 2024
Another great 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:
Once again, we had a great experience. The unit was clean and well maintained. I would highly recommend Compass Realty to friends.
Timothy F.
From a partner site
10/10 Excellent
Timothy F.
25 November 2024
Another great 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:
Once again, we had a great experience. The unit was clean and well maintained. I would highly recommend Compass Realty to friends.
Timothy F.
Verified
8/10 Good
Douglas P.
1 December 2022
Liked: Cleanliness, communication
Key West Thanksgiving
Very clean, comfortable beds. Check-in could have been better. Long way from front office to condo. Condo not in an optimal spot. Location is only drawback.
Douglas P.
Stayed 8 nights in Nov 2022
Response from VrboOwner on 1 February 2023
Thank you for sharing a review of your recent experience Douglas. Our team here at Compass Realty is committed to providing high-quality customer service. We look forward to welcoming you again! Thank you for being our guest!
From a partner site
10/10 Excellent
Shawn B.
18 November 2022
Island Breezes
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. We will definitely stay here again. I loved the decor as it was very uplifting and appropriate for Key West. A few other condos in the same location we not as nice.
Shawn B.
Verified
10/10 Excellent
Donald C D.
29 June 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Review
Good experience
Donald C D.
Stayed 7 nights in Jun 2022
Verified
8/10 Good
Morna C.
18 May 2022
Liked: Cleanliness, location, listing accuracy
Disliked: Check-in
No comment
No comment
Morna C.
Stayed 8 nights in May 2022
From a partner site
10/10 Excellent
18 May 2022
Great Property
Rating Details:
The property manager was more than 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 very much enjoyed our stay. Very comfortable and well supplied with everything needed. Everything is in good shape and fresh. We will be going back again.
From a partner site
10/10 Excellent
Jason B.
18 May 2022
Great 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:
The place had everything you need. Great location and pretty well kept grounds.
Jason B.
From a partner site
10/10 Excellent
Nancy H.
18 May 2022
We loved our stay at Island Breezes!
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 always enjoy staying at Truman Annex. After a full day of fun, it's so nice to come "home" to a beautiful and quiet setting. The other guests are friendly, the units are well furnished, and we're always sad when we have to leave!
Nancy H.
Verified
10/10 Excellent
Justin L.
19 July 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place, great location!
Loved staying here, the location is great. If you are traveling with two kids this place is perfect. There is a splash pad nearby, the beach is walkable, the Duval loop is close.
Justin L.
Stayed 8 nights in Jun 2021
Verified
10/10 Excellent
Angie H.
15 July 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Highly recommend
We were looking for a place to stay in the heart of Key West and all the attractions. We were so pleased to find this property as it had all the amenities we needed. Very smooth process and affordable.
Angie H.
Stayed 7 nights in Jun 2021
Verified
10/10 Excellent
Rebekah M.
8 June 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location!
Of all the three times we’ve stayed in Key West, this was my favorite! You are literally within walking distance to the water park/playground (great for my 2 year old), and the pier by the navy ship which I now consider the best sunset viewing spot. You could also walk or bike to the nearest beach. The place itself was very cute and cozy and the front and back balconies were very nice. Plenty of towels provided and loved that it had a washing machine and dryer in the unit! Would totally stay here again!
Rebekah M.
Stayed 13 nights in May 2021
Verified
10/10 Excellent
Chuck E.
29 October 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Smooth and enjoyable
Everything went as we expected from past experiences renting in the Annex
Chuck E.
Stayed 7 nights in Oct 2019
Verified
8/10 Good
Brenda A.
22 March 2019
The condo was well furbished and very comfortable.
The process of working with Campass Reality was confusing and difficult. I did not like to sign an additional contract with another company when renting through VBRO. There were lots of fines for not washing dishes or taking out trash when I had already paid a cleaning fee. There were changes in when to check out. The water in the kitchen was brownish and undrinkable. I had numerous calls from the Campass reality that were annoying and not needed. The location was excellent and it would have been nice to have a few beach chairs.
Brenda A.
Stayed 7 nights in Mar 2019
Verified
10/10 Excellent
Lili C.
8 January 2019
Clean & Comfy
Overall we had a lovely stay in Island Breezes. I was originally worried the apt would be a little run down from the pics with old wicker furniture and and old kitchen but in the end the apt was perfectly comfortable and was super clean. There is everything you need and plenty of fresh towels and pillows etc. A/C, TV and Wifi works well and check in and check out is super convenient with the realty office close to the apt. The back awning is broken so apt gets a little hot by the afternoon but luckily there's the front balcony that nice and shady (and the A/C works great to cool the apt down quickly). I would recommend this apt to anyone who wants a clean comfy place close to everything and with easy parking...
Lili C.
Stayed 14 nights in Dec 2018
About the host
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