Island Breezes WEEKLY RENTAL at the Truman Annex in Key West

Photo gallery for Island Breezes WEEKLY RENTAL at the Truman Annex in Key West

A bright room with wicker furniture, a framed painting, and a view to the outside.
A water park with a slide, a water fountain, and palm trees at sunset.
A room with a sofa and chairs, a dining table, and a framed picture on the wall.
A landscaped garden with palm trees, shrubs, and a gravel path.
A covered porch with a white railing, overlooking a residential area with houses and palm trees.

Reviews

9.6 out of 10
Exceptional

Highlights

  • Onsite parking available
    Convenient and secure onsite parking, a rare amenity in the area.
  • Discover nearby landmarks
    Walk to Duval Street

Popular amenities

  • Balcony
  • Swimming pool
  • Air conditioning
  • Off-street parking available
  • Refrigerator
  • Washer

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

1 bathroom

Bathroom 1

Bathtub or shower

Spaces

Kitchen
Balcony
Separate dining area

Add dates for prices

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About the neighborhood

Key West

Located on the waterfront, this condo is in Old Town Key West, a neighborhood 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. Ready for a night out? Consider The Key West Theater and Sloppy Joe's Bar. 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.
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 - 8 min walk - 0.7 km
  • Fort Zachary Taylor Historic State Park - 8 min walk - 0.7 km
  • Mallory Square - 12 min walk - 1.1 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
  • ‪Mangoes Restaurant - ‬7 min walk

Frequently asked questions

Does Island Breezes WEEKLY RENTAL 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 WEEKLY RENTAL at the Truman Annex in Key West?

As of Oct 29, 2026, prices found for a 1-night stay for 2 adults at Island Breezes WEEKLY RENTAL at the Truman Annex in Key West on Apr 24, 2027 start from $559, 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 WEEKLY RENTAL at the Truman Annex in Key West pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Island Breezes WEEKLY RENTAL at the Truman Annex in Key West?

Check-in begins at 4:00 PM.

What time is check-out at Island Breezes WEEKLY RENTAL at the Truman Annex in Key West?

Check-out is at 10:00 AM.

Where is Island Breezes WEEKLY RENTAL 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

9.6

Exceptional

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. 21 out of 25 reviews
Rating 8 - Good. 3 out of 25 reviews
Rating 6 - Okay. 1 out of 25 reviews
Rating 4 - Poor. 0 out of 25 reviews
Rating 2 - Terrible. 0 out of 25 reviews

9.8/10

Cleanliness

9.2/10

Check-in

9.4/10

Communication

9.6/10

Location

9.6/10

Listing accuracy

Reviews

From a partner site

10/10 Excellent

Another 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 property was in a great location as usual! We rent from Compass every year and they never disappoint. The property is always clean and well stocked with essentials We will come back next year for sure!!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Good communication throughout, property was as described and to a high standard. Had everything we needed.
Stayed 14 nights in Oct 2025
Response from VrboOwner on Nov 17, 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 review

10/10 Excellent

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.
Stayed 7 nights in Dec 2022
Response from VrboOwner on Feb 9, 2023
Thanks for staying with Compass Realty!
From a partner site

10/10 Excellent

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.
Stayed 7 nights in Apr 2023
Response from VrboOwner on Jul 12, 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

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.
Verified review

10/10 Excellent

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

Great

No problem
Stayed 10 nights in May 2025
Response from VrboOwner on Jun 4, 2025
Thanks for staying with Compass Realty!
From a partner site

10/10 Excellent

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.
Response from VrboOwner on Jul 19, 2023
Thanks for staying with Compass Realty!
From a partner site

10/10 Excellent

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.
From a partner site

10/10 Excellent

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
Stayed 7 nights in Apr 2024
Response from VrboOwner on May 23, 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

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.
Verified review

6/10 Okay

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.
Stayed 14 nights in Feb 2023
Response from VrboOwner on Jul 12, 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

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.
Verified review

8/10 Good

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.
Stayed 8 nights in Nov 2022
Response from VrboOwner on Feb 1, 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

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.
Verified review

10/10 Excellent

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

Review

Good experience
Stayed 7 nights in Jun 2022
Verified review

8/10 Good

Liked: Cleanliness, location, listing accuracy
Disliked: Check-in

No comment

No comment
Stayed 8 nights in May 2022
From a partner site

10/10 Excellent

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.
From a partner site

10/10 Excellent

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

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!
Verified review

10/10 Excellent

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.
Stayed 8 nights in Jun 2021
Verified review

10/10 Excellent

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.
Stayed 7 nights in Jun 2021
Verified review

10/10 Excellent

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!
Stayed 13 nights in May 2021
Verified review

10/10 Excellent

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

Smooth and enjoyable

Everything went as we expected from past experiences renting in the Annex
Stayed 7 nights in Oct 2019
Verified review

8/10 Good

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.
Stayed 7 nights in Mar 2019
Verified review

10/10 Excellent

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...
Stayed 14 nights in Dec 2018
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