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From $275 / night help
Estimated Price for guests,

Description from manager

Description from manager

Bedrooms 2 / Bathrooms 2 / Sleeps 4 / House
Bedrooms: 2  Bathrooms: 2   Sleeps: 4  Type: House

2 Unknown types

Leeward Isle Key West Retreat
TripAdvisor property ID 2354106

More Property Details

Book this 2 bedroom house in Key West today! A total of 4 people can sleep here comfortably.

Travelers are sharing their opinions on this property. It has an overall rating of 4.5/5 thanks to an average of 35 reviews.

The manager last updated the property’s calendar Feb 19, 2018.

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About the manager

About the manager

At Home In Key West, Inc.
Calendar last updated:
19 Feb 2018
Overall rating:

Languages spoken: English, Czech, Russian



This owner does not use online booking. Please contact them and they will be able to offer you a secure way to pay for your stay. Never pay for your vacation rental by wire transfer (such as Western Union or Moneygram) as this type of payment is untraceable.
Please contact the owner
Cancellation policy
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Proximity to TripAdvisor's Top Key-west Attractions



Phone / Internet

  • Internet access
  • Wireless Internet

Pool / Spa

  • Private outdoor pool (heated)
  • Shared outdoor pool (unheated)

Property Features

  • Parking


  • Fridge
  • Microwave
  • Stove
  • Toaster


  • Satellite TV


  • Balcony or terrace


  • Children
  • Pets
  • Smoking - Ask


  • 2 Unknown types


Reviews (35)

Very Good – based on 35 reviews Very Good
35 reviews

Very Good

“A little piece of paradise”

Reviewed 9 Aug 2015

This house is just beautiful and come equipped with everything you need for a wonderful vacation. The development is small a quiet and feels like an oasis. It is steps from all the action on Duval Street and in walking distance of most things in Key West. Perfect house in a perfect location.

“Nicely Updated and Well Maintained”

Reviewed 1 Aug 2014

My wife and I stayed here in July 14. Windward Park is a small (13 units) gated townhome community convenient to Duvall street, but away from the traffic and noise. Unit has been nicely updated and was very well maintained. Pool is right out front door and is a good size pool. We did not have a car (walked everywhere), but parking is available for 1 car. Unit had everything we needed, including WiFi and a washer and dryer. There are two bedrooms upstairs with a shared bath. Other full bath is on the main floor. We would definitely stay here again and would book through At Home Key West again.

“A home from home”

Reviewed 20 Jul 2014

A lovely property, even better than the photos. Beds were very comfortable and all equipment worked well. Nice to have the pool right outside but it was busy with children quite often so didn't get as many serene floats on the lilo as I would've liked. House gets the morning sun on the porch deck and then nice and shady for the day. Great to have a washer/dryer and lots of towels supplied. Lots of info on the area left by the owners which was useful. Located the quiet end of Duval St so a good 15 min walk up to Mallory Square and Harbourwalk.


Reviewed 3 Apr 2014

The complex is very nice. The community pool is very large for the area. You are walking distance from Duval Street and every other site. Rent a small car! You won't need it and the parking spaces are small! One bathroom is on the main floor, and the other other on the second floor. If you have two couples, one will have to go downstairs to shower, etc. Both bedrooms are upstairs. Very nice home. Bring your walking shoes! you will need them.


Reviewed 26 Dec 2013

My wife, youngest daughter and I spent 8 days at the Leeward Isle unit of Windward Park on Truman Key West just before Christmas in 2013. Since we vacation several times a year, we have experienced many beautiful and complete condos, homes, hotels, etc. Carole,my wife, usually spends many hours researching and choosing our vacation retreat. She did so for our month long stay in Key West in July of 2013. Since we had only eight days to commit in December, we were unable to stay in that same penthouse.Thus, I came upon Leeward Isle because I noted the complex during my daily walks to the gym in July.I can honestly say that this was the first time our unit was exactly what it appeared to be on the internet. Libby, from the rental agency, also described it to perfection. Everything was perfect. There was not need to take anything except our clothes and personal items. The pool is great. The guests in the other units were all very respectful. There was no nighttime noise. I had already knew that the location was great. We were close enough to Duval Street to access all that we intended to, yet, far enough away to be removed from the noise and traffic. The furnishings and amenities were were all modern, clean and in great condition. Upon our arrival we had an issue with the television in the master bedroom. Staff was there in less than 30 minutes after our call. Wow! There is also a designated parking space for a vehicle or electric car. There was also a bike rack to secure our rental bicycle. This is a perfect unit for up to three people.

“Awesome vacation in Key West!”

Reviewed 8 Aug 2013

Our family spent a week in Key West and loved staying at this condo. It was within walking distance to Duval St. and a very short drive to everything else we did. The condo was exactly as the pictures showed and had everything we needed. We had a little outside private area surrounded by a picket fence that was just a few steps to the pool.


Reviewed 11 Jul 2013

This property was perfect for a much needed get away. It has everything you need and was very very clean. Complex was very small and private. Only a short walk to Mallory Square and just around the corner from Duval Street. Rental company was extremely user friendly. I can't wait to make a return trip!

“Key West vacation”

Reviewed 6 Jun 2013

We loved the property the location was perfect, right near everything. Easy access everywhere. The rental was beautiful, and fully appointed. The grounds were well maintained. Whoever maintains their orchids does a great job. The service from at Home in Key Wes was wonderful. Although we never saw anyone in person due to our arrival hour and departure, there we no problems. Only issue, who to call at night when other tenants were loud. We had someone from Maine in another unit who thought the pool was open all night. We had no one to contact. Beautiful place, great location, great customer service. Will use again.

Response from the manager Thank you for taking the time to review our home. We love to hear when guests enjoy their stay with us. Regarding contact after office hours, we have someone On-Call 24/7 and offer that phone number in numerous places on our check-in paperwork for just this sort of instance. We will be sure to point that out when you return.


Reviewed 26 Dec 2012

We stayed at the Leeward Isle Key West Retreat in Dec. 2012 for 10 days. In our opinion this is a very unique property to the Key West area. The condo was equiped with all the necessary (and then some) items to make our stay enjoyable. What makes this property unique is the size, privacy and location. Some locations have one or two of the three, but this location has it all. We were within easy walking distance to all attractions and night life in the area. I would highly recommend this property and will stay here again when we go back to Key West.

“Wonderful trip”

Reviewed 25 May 2012

Leeward Isle Key West Retreat was a wonderful place to stay. The unit was in great condition and in a great location. It was just close enough to Duval street for daytime activities with a young family and plenty quiet at night. We thoroughly enjoyed our time here and are looking forward to going back.

Review 1-10 of 35