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Entire condo

Island Breezes at the Truman Annex in Key West

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

A heated pool - Island Breezes at the Truman Annex in Key West (Key West)
Property grounds - Island Breezes at the Truman Annex in Key West (Key West)
Living area - Island Breezes at the Truman Annex in Key West (Key West)
Living area - Island Breezes at the Truman Annex in Key West (Key West)
Property grounds - Island Breezes at the Truman Annex in Key West (Key West)
Nestled in the award-winning Truman Annex, this charming condominium offers views of the Truman Waterfront Park and Florida Keys Eco Discovery Center. Take a dip in the community pool or explore nearby Fort Zachary Taylor State Park and Beach.

Reviews

9.6 out of 10
Exceptional

Entire condo

2 bedrooms1 bathroomSleeps 4

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

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.

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.

Property amenities

Pool/Spa

  • Communal pool
  • Heated pool

Internet

  • Available in the condo: Free WiFi

Parking and transportation

  • Onsite parking includes off-street options

Kitchen

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

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Bathtub or shower
  • Towels provided

Living spaces

  • Separate dining area

Outdoor areas

  • Balcony

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center
  • Near the marina
  • Near the sea
  • On the waterfront

Things to do

  • Heated pool
  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling 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)
  • Fire extinguisher
  • Deadbolt lock

General

  • Gated community
  • Unit size: 1 square foot

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  • Spa
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The price is ￥46,026
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Policies

Check-in

Check-in time starts at 4:00 PM

Contactless check-in 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

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 fire extinguisher and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
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

About the neighborhood

Located on the waterfront, this condo is in Old Town Key West, a neighborhood in Key West. Southernmost Point and Ernest Hemingway Home and Museum are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. 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. Visit our Key West travel guide
View more Condo Rentals in Key West
Map
FL, Key West

What's nearby

  • Florida Keys Eco - Discovery Center
    Florida Keys Eco - Discovery Center
    3 min walk - 0.3 km
  • Duval Street
    Duval Street
    6 min walk - 0.5 km
  • Ernest Hemingway Home and Museum
    Ernest Hemingway Home and Museum
    8 min walk - 0.7 km
  • Fort Zachary Taylor Historic State Park
    Fort Zachary Taylor Historic State Park
    8 min walk - 0.7 km
  • Florida Keys National Marine Sanctuary
    5 min walk - 0.4 km

Getting around

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

Restaurants

  • Green Parrot Bar
    4 min walk
  • Blue Heaven
    8 min walk
  • Mangoes Restaurant
    7 min walk
  • Moondog Cafe & Bakery
    8 min walk
  • Rams Head Southernmost
    7 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.

Is Island Breezes 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 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?

Check-out 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.

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Island Breezes at the Truman Annex in Key West Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travelers 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. 20 out of 24 reviews
Rating 8 - Good. 3 out of 24 reviews
Rating 6 - Okay. 1 out of 24 reviews
Rating 4 - Poor. 0 out of 24 reviews
Rating 2 - Terrible. 0 out of 24 reviews

9.8

Cleanliness

9.4

Location

Reviews

From a partner site

10/10 Excellent

Jim C.

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
From a partner site

10/10 Excellent

Timothy F.

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

Timothy F.

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

10/10 Excellent

Timothy S.

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
Verified

10/10 Excellent

Andrew B.

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
From a partner site

10/10 Excellent

Lora C.

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
Verified

10/10 Excellent

robert s.

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

Great

No problem
Stayed 10 nights in May 2025
From a partner site

10/10 Excellent

Laura W.

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.
From a partner site

10/10 Excellent

Deborah H.

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.
From a partner site

10/10 Excellent

Joyce K.

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

6/10 Okay

karen b.

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
Verified

8/10 Good

Douglas P.

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
From a partner site

10/10 Excellent

Shawn B.

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

10/10 Excellent

Donald C D.

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

Review

Good experience
Stayed 7 nights in Jun 2022
Verified

8/10 Good

Morna C.

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

Jason B.

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

Nancy H.

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

10/10 Excellent

Justin L.

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

10/10 Excellent

Angie H.

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

10/10 Excellent

Rebekah M.

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

10/10 Excellent

Chuck E.

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

8/10 Good

Brenda A.

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

10/10 Excellent

Lili C.

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