Villa vacation rentals in Key West

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Popular amenities for Key West villa rentals

Luxury villa rentals

Guest favourite
Villa in Islamorada
5 out of 5 average rating, 32 reviews

Anglers Reef Islamorada

NicoleRating, 5 stars1 month ago
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 in Marathon
4.67 out of 5 average rating, 3 reviews

Villa Sombrero

NikkiRating, 5 stars28 months ago
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.
Villa in Key Largo
5 out of 5 average rating, 3 reviews

Dolphin 1-Bedroom Villa

KellyRating, 5 stars37 months ago
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.
Villa in Islamorada
4.86 out of 5 average rating, 7 reviews

3 EnSuite Bedrooms! Waterfront Resort, Pool, Dock!

MeghanRating, 5 stars3 weeks ago
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!
Villa in Key Largo
4.79 out of 5 average rating, 68 reviews

Oceanfront Villa overlooking the Atlantic

ShannonRating, 5 stars25 months ago
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!
Guest favourite
Villa in Marathon
5 out of 5 average rating, 10 reviews

Waterfront Villa (38) w/ sunset views & boat slip

KatrinRating, 5 stars4 weeks ago
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!!
Villa in Marathon
4.83 out of 5 average rating, 24 reviews

"Casa Azul Villa" Oceanfront-Marathon-8Guests-Dock

EdithRating, 5 stars2 months ago
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!
Guest favourite
Villa in Islamorada
5 out of 5 average rating, 6 reviews

Scenic Resort w/ Outdoor Pool | Florida Keys Stay

JackieRating, 5 stars1 month ago
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

Villa in Duck Key
4.35 out of 5 average rating, 20 reviews

2BR water view with private pool, balcony & kayak

JennaRating, 5 stars2 months ago
very comfortable villa. Absolutely loved the little swimming pool. Clean and comfortable villa.
Top guest favourite
Villa in Marathon
5 out of 5 average rating, 21 reviews

Indigo Reef water view Villa- #1 Guest Favorite

CaitlinRating, 5 stars1 week ago
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.
Villa in Islamorada
5 out of 5 average rating, 3 reviews

Isla Mamey: Waterfront Htd Pool, Dock, Walkable

TanyaRating, 5 stars8 months ago
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!
Guest favourite
Villa in Islamorada
4.88 out of 5 average rating, 16 reviews

Islamorada house with best location. Lic # 24-0055

SabraRating, 5 stars4 weeks ago
Perfect place for the family! Kid friendly and cozy. Beds were very comfortable and everything was very clean. We will definitely stay here again.
Villa in Key Largo
4.85 out of 5 average rating, 46 reviews

2bd/2ba Ocean Retreat in Kawama Yacht Club

JanetRating, 5 stars4 weeks ago
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!
Villa in Key Largo
4.46 out of 5 average rating, 13 reviews

Guest Spring Break Stay: Resort Amenities & Views

LestrydRating, 5 stars1 month ago
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.
Guest favourite
Villa in Islamorada
4.83 out of 5 average rating, 6 reviews

Isla Mirabelle: Waterfront Pool, Dock, Walkable

JeffryRating, 5 stars2 months ago
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

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Key West
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