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Island Breezes at the Truman Annex in Key West

Condo near Duval Street in Key West

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

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

Reviews

9.6 out of 10
Exceptional

Entire condo

2 bedrooms1 bathroomSleeps 4

Popular amenities

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

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

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About the area

Key West

Seaside stay .Within a 10-minute walk of this Old Town Key West condo, you'll find Duval Street and Ernest Hemingway Home and Museum. Also, Mallory Square is within half a mile (1 km) and Florida Keys Beaches is within 2 miles (3 km).
View more Condo rentals in Key WestOpens in a new window

What's nearby

  • Florida Keys Eco - Discovery Center - 3 min walk - 0.3 km
  • 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

Getting around

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

Restaurants

  • ‪Blue Heaven - ‬8 min walk
  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Margaritaville - ‬7 min walk
  • ‪Moondog Cafe & Bakery - ‬8 min walk
  • ‪Mangoes Restaurant - ‬7 min walk

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.

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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

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

  • No pets 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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. 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. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a fire extinguisher, a smoke detector, and a deadbolt lock in each accommodation.

Property is also known as

Breezes The Truman Annex
Island Breezes in the Truman Annex
Island Breezes @ the Truman Annex Key West
Island Breezes @ the Truman Annex Private vacation home
20% Off Summer Special Island Breezes @ the Truman Annex
Island Breezes @ the Truman Annex Private vacation home Key West
2698-193305

Frequently asked questions

How close is Island Breezes at the Truman Annex in Key West to the airport?

This condo is 4.1 mi (19-min drive) away from the Key West Intl. Airport (EYW) airport, the closest popular airport to the property.

Does Island Breezes at the Truman Annex in Key West have an airport shuttle?

Airport shuttle services are not available at this condo.

How close is Island Breezes at the Truman Annex in Key West to the beach?

This condo is a short 14-minute walk from Florida Keys Beaches and 0.8 mi (8-min drive) from South Beach. Don't forget your sunscreen!

Does Island Breezes at the Truman Annex in Key West offer free breakfast?

This condo does not offer free breakfast.

Is there a casino at Island Breezes at the Truman Annex in Key West?

No, there is no casino at this condo.

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

Check-in begins at 4:00 PM.

Is there free parking at Island Breezes at the Truman Annex in Key West?

Free parking is not available at this condo.

Does Island Breezes at the Truman Annex in Key West have a pool?

Yes, there's a heated pool.

Does Island Breezes at the Truman Annex in Key West have a spa?

There are no spa services available at this condo.

How close is Island Breezes at the Truman Annex in Key West to downtown Key West?

This condo is 0.2 mi away from Key West.

Island Breezes at the Truman Annex in Key West Reviews

Reviews

9.6

Exceptional

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

9.8/10

Cleanliness

Reviews

Verified review

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 review

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
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.
Verified review

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

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

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

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

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 review

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
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 review

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 review

10/10 Excellent

Donald C D.

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

Review

Good experience
Stayed 7 nights in Jun 2022
Verified review

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 review

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 review

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 review

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 review

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 review

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 review

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