Virtual Tour
USA Florida Key West Old Town Key West Listing #10732

Leeward Isle - Key West, FL

21 reviews
Max occupancy: 6 2 King Bed 2 bedrooms 1 bathroom Sleeps 4 comfortably  4 dog max  (30 lb weight limit) 
529 Olivia St, Key West, FL 33040

Worry-free booking

Enjoy peace of mind with flexible travel options:

  • At least 7 days before check-in: You can reschedule your trip, or cancel and receive 100% of the cost as a Future Stay Credit.
  • At least 30 days before check-in: You also have the option to cancel for a refund (minus the booking fee).

Expert cleaning

Professional housekeepers clean and stock each home, using an EPA-approved disinfectant.

Local support

Each trip is backed by 24/7 customer support and local teams everywhere we operate.


Many Vacasa homes use smart locks or lockboxes for a smooth, contactless check-in.

Cozy cottage w/ private hot tub, tranquil garden & parking - dogs OK!

Bask in the peaceful sunshine of Key West and feel all your stress melt away when you stay at this cozy dog-friendly cottage right in town. With a private hot tub in the garden area out back plus all the conveniences of home, what's not to love?

Sitting only half a block from all the fun and excitement of Duval Street, park your car in the private space and forget about it - you'll be able to walk or bicycle everywhere you want to go. Head to the Southernmost Point and check out the Key West Butterfly and Nature Conservatory while you're at it, then head north to check out Mallory Square and other historical landmarks along the way.

Spend quiet mornings in the garden, sipping coffee and eating a delicious breakfast prepared in your fully equipped kitchen. After a full day of exploring, come back for a relaxing soak in the hot tub, watch a show on the flatscreen cable TV, and surf the free WiFi to find activities for tomorrow. A dog is welcome for a small nightly fee.

Make sure your Florida vacation is exactly how you imagine - book this charming cottage today!

A damage waiver, covering up to $2,000 of accidental damage to the property or its contents, is included in the cost of your reservation.

You must be 25 years or older to rent this property.

Property permit ID: 25230-102546




Heating & cooling

Partial AC

Kitchen & dining





Internet : Comcast


Cable : Comcast

Wireless router

On-site activities

Hot tub : Private




21 reviews

Norine S. Oct 2020
Great porch for sitting and watching passerby’s any time of day. Tropical oasis in the back.
Amenities and space inside to make your stay a pleasure.
Vacasa staff prompt with responses, friendly and polite.
No extra charge for the neighborhood roosters!
Jamie B. Aug 2020
Loved the location , the outdoor shower, the coziness of it !! The front porch just to watch the world go bu!
Lisa P. Jul 2020
Excellent location and great cottage. Perfect for a stay Key West.
Randy H. Jan 2020
location of house and hot tub
Rick M. Sep 2019
Great house, location.
Giulia P. Aug 2019
Appartamento carino, comodo e pulito. Dotato di tutti i comfort e vicino ai negozi
ERIC P. Jul 2019
Clean comfortable beds, lots of towels. Good air conditioning and the off street parking is a BIG plus.
Michael D. Apr 2019
Located perfect distance from everything whether it be Duval or the beaches on the other side. Super clean and roomy. Only thing to keep in mind is the Bobby’s Monkey Bar gets jamming on the weekend so there will be noise from that. With that said our 16 month old slept right through it so no biggie. Would definitely stay here again!
Jen S. Mar 2019
We had a great time in Key West and loved our stay at Leeward Isle. The home is clean and has everything you need for your stay. We were fortunate to meet the owner during our stay and he was very nice and asked if there was anything we needed. The beds are comfy and the outside shower is fantastic! Perfect location and easy to get to anywhere. I would definitely recommend this rental and would stay here again. Vacasa made the rental experience easy!
Nancy G. Feb 2019
Central location in Old Town Key West. Comfortable beds, great outdoor space.
Marc M. Feb 2019
Bien situé. Spa et court arrière superbe
Malheureusement Secteur très très bruyant
Debra T. Feb 2019
We enjoyed our stay at Leeward Isle. The house is a cute little bungalow. We really appreciated the off street parking as the location is within easy walking distance to wonderful restaurants and will especially appreciate this as parking is difficult in Key West. A friendly rooster crowed every morning so we did wake up a bit earlier than planned but we enjoyed his visits to the back yard! Our back yard was very peaceful & private... lush landscaping & fully fenced. Overall, we had a wonderful stay!
Leonard P. Nov 2018
Nice place to stay and walk old key west
Thomas B. Sep 2018
Sehr gemütliches Ambiente in Key West eine super tolle Lage!! Perfekt Ur Ausflüge, wunderbar sauber und einfach wundervoll das Haus!! Danke für diesen tollen Tag!! Wie kommen immer gerne wieder zurück!!
Martin M. Jun 2018
House was awesome, location fantastic, had A1 time.
Michael F. Apr 2018
Great Place to stay! For a two bedroom 1 bath it’s very spacious. Would rent here again!!!
Teresa S. Mar 2018
The Location was good with the exception of the Monkey Bar down the street that was really loud until 4:00Am (turn on the Air conditioner to drown out the noise.) The property was really nice. It has a nice front porch two really nice bedrooms and a quaint little garden out back. A few short blocks to Duval and other attractions.
Diane M. Mar 2018
Richard D. Feb 2018
This house is great for 4-6 guests. Very comfortable. Only one bathroom but we managed fine. Cute little kitchen with coffee pot, fridge and stove.

Walking distance to all the bars and restaurants.