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Entire condo

Island Breezes WEEKLY RENTAL!

Condo with patio, 6-minute walk to Duval Street

Photo gallery for Island Breezes WEEKLY RENTAL!

Pool - Island Breezes WEEKLY RENTAL! (Key West)
Living area - Island Breezes WEEKLY RENTAL! (Key West)
Property grounds - Island Breezes WEEKLY RENTAL! (Key West)
Property grounds - Island Breezes WEEKLY RENTAL! (Key West)
Living area - Island Breezes WEEKLY RENTAL! (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

  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space
  • 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.

Island Breezes WEEKLY RENTAL!

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

Internet

  • Available in the condo: Free WiFi

Parking and transport

  • Onsite parking includes off-street options

Food and drink

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

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Bathtub or shower
  • Towels provided

Outdoor areas

  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city centre

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 not reported (host has not indicated whether there is a smoke detector on the property)

General

  • Gated community
  • Unit size: 1 square foot

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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 not indicated whether there is a smoke detector on the property
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

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

About the area

Located in Key West, this condo is in the city centre. 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. Visit our Key West travel guide
View more Condo rentals in Key West
Map
Key West, Florida

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 Island Breezes WEEKLY RENTAL! pet-friendly?

No, pets are not allowed at this property.

How much is parking at Island Breezes WEEKLY RENTAL!?

On-site parking is available at the property.

What time is check-in at Island Breezes WEEKLY RENTAL!?

Check-in begins at 4:00 PM.

What time is check-out at Island Breezes WEEKLY RENTAL!?

Checkout is at 10:00 AM.

Where is Island Breezes WEEKLY RENTAL! 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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Island Breezes WEEKLY RENTAL! Reviews

Reviews

Exceptional

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. 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

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

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

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

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.

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

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

10/10 Excellent

robert s.

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

Great

No problem
Stayed 10 nights in May 2025
This review comes from a trusted partner site and has not been verified.

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

10/10 Excellent

Laura W., FORISTELL

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

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

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.

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

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

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.

10/10 Excellent

Donald C D.

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

Review

Good experience
Stayed 7 nights in Jun 2022

8/10 Good

Morna C.

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

No comment

No comment
Stayed 8 nights in May 2022
This review comes from a trusted partner site and has not been verified.

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

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

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!

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

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

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

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

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

10/10 Excellent

Lili C., Brooklyn, NY

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