
Villa vacation rentals in Key West
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Top-rated villa rentals in Key West
Guests agree: these villas are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Key West villa rentals
Private villa rentals

Isla Guava: Waterfront Htd Pool, Dock, Walkable
Amazing place, you can’t beat the location and property. The house was exceptionally clean and the host was very friendly and easy to communicate with. We will definitely return!!

Picturesque Villa Near History of Diving Museum
Beautiful home away from home - great kitchen, everything white and natural Inside, easy parking, lovely pool and private veranda to have a sunset drink. We loved it. Even though I booked a 2/2, there was only ONE bathroom. Make sure to double check you are getting two bathrooms - we managed but I felt a little disappointed because that was my search criteria on air bnb and a must-have. Besides that we loved that there is a golf shuttle to the main hotel. We will be back ! A lovely get away in the Keys

2BR oceanfront with amazing views, balcony & kayak
It was quiet and comfortable. Very clean throughout. Beautiful location. Loved the decks upper and lower. I would rent again.
Luxury villa rentals

Anglers Reef Islamorada
Our family of 5 loved our time in Islamorada. The community was beautiful and quiet. It was definitely mostly retired couples but everyone was friendly with our young kids. The condo was bigger than the pictures made it seem- we had more than enough space. Everything was clean and we had everything we needed.

Villa Sombrero
We had a wonderful time. The neighborhood is beautiful, super quiet and nice to walk around. We used the provided paddle boards to go to nearby Sombrero Beach which was lovely. We also walked to Publix and Walgreens. The house itself is really two houses - one upstairs and one downstairs - each with their own kitchens, bedrooms and bathrooms. The house itself is simple and utilitarian, but backyard area is really spectacular. We spent the vast majority of our time outside lounging, playing tennis or swimming in the pool. The location also makes for an easy day trip to Key West. The property manager Jesús was extremely responsive and took care of everything we needed.

Dolphin 1-Bedroom Villa
A beautiful quiet place to stay. Kayaking in the morning and swimming in the pool at night. We loved exploring other Florida Keys and coming back to sleep. Easy check in and out.

3 EnSuite Bedrooms! Waterfront Resort, Pool, Dock!
This house was perfect for our family of 5 for Spring Break. The canal at the back was perfect for fishing, kayaking and SUP. The pool was lovely and warm. The house and grounds were so beautiful and comfortable! We had a wonderful time and would stay here again in a heartbeat!

Oceanfront Villa overlooking the Atlantic
My family really enjoyed our stay at Vivian’s place! The photos do not do it justice! Very roomy, amazing water views, and beautiful decor/upgrades. Vivian had everything we needed for our stay - we traveled with a toddler and baby and everything we needed was there. Vivian was responsive and helpful. We would definitely stay again! Thanks Vivian!

Waterfront Villa (38) w/ sunset views & boat slip
Great location on the property. Beautiful view of the water and the pool. Nice big porch to relax on with plenty of chairs. Provided plenty of towels and the kitchen had everything you needed. Could have used more TB, PT and some dishwasher soap but all good. This place is a favorite of ours to just relax and go boating! Highly recommend!!

"Casa Azul Villa" Oceanfront-Marathon-8Guests-Dock
This place was decorated beautifully! Very unique furnishings and decorations were fun! Outside area was beautiful. Spent every day there! Sunsets from the end of the dock were beautiful! The landscaping was spot on, even some orchids in the trees! Loved the colorful dishes and modern appliances, and the coffee pods were awesome! I am getting the same machine now! Privacy and quiet neighborhood is hard to find in some areas of the keys. Walked several days on the street. Nice towels, beach towels and comfortable sheets, pillows and throws. My husband loved the fake fur one in the LR! Thank you for the lovely stay!

Scenic Resort w/ Outdoor Pool | Florida Keys Stay
Very nice townhouse, it was also really convenient to call the golf cart and go to the larger resort, which was beautiful.
Villa rentals with a pool

2BR water view with private pool, balcony & kayak
very comfortable villa. Absolutely loved the little swimming pool. Clean and comfortable villa.

Indigo Reef water view Villa- #1 Guest Favorite
We absolutely loved our stay and can’t wait to return! The unit was pristine and we loved watching the sunsets from the porches. The pool was pristine and never crowded. The hosts were amazingly responsive and helpful.

Isla Mamey: Waterfront Htd Pool, Dock, Walkable
Our family of 4 stayed for 11 nights to celebrate our twins 10th birthday. We live in Miami and brought most of our kitchen but totally wasn’t needed! Villa #5 has anything and everything kitchen wise! Everything was so clean and comfortable - need to upgrade our home pillows to match! Shared pool was always clean and warm, met so many nice people. Evening dock was awesome for catching small fish with the kids. Location is perfect for all the dining Islamorada has to offer. We can’t wait to go back! Thanks again!

Islamorada house with best location. Lic # 24-0055
Perfect place for the family! Kid friendly and cozy. Beds were very comfortable and everything was very clean. We will definitely stay here again.

2bd/2ba Ocean Retreat in Kawama Yacht Club
A beautiful unit, nice beds and everything as pictured! Paul was good on communication. However, the small community at Kawama is becoming over- crowded. Many times the pools are full and over capacity with screaming kids, and no chairs are available to just sit by the pool. Large parties are happening most every weekend, with a lot of drinking, smoking, and loud music. It’s not Paul’s fault, but the atmosphere here isn’t as quiet and kid friendly as it used to be!

Guest Spring Break Stay: Resort Amenities & Views
Our stay at this house was absolutely perfect! The home itself was spacious, beautifully maintained, and had everything we needed for a comfortable and relaxing getaway. What made it even better was the access to the resort amenities like pools, restaurants, and activities, all just a short distance away. It truly felt like having the best of both worlds: the privacy of a home with the luxury of a resort.

Isla Mirabelle: Waterfront Pool, Dock, Walkable
The property was better than described. A great quiet getaway. At the same time a lot to do for all. For kids, a playground, park and library adjacent to the property. This is beyond what is available throughout the Keys. Looking forward to our next stay.
Quick stats about villa rentals in Key West
Total rentals
10 properties
Nightly prices starting at
$333 CAD before taxes and fees
Total number of reviews
150 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with a pool
10 properties have a pool
Wifi availability
10 properties include access to wifi
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