Villa vacation rentals in Key West

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Popular amenities for Key West villa rentals

Villa rentals with a pool

Guest favorite
Villa in Islamorada
5 out of 5 average rating, 34 reviews

Anglers Reef Islamorada

DeborahRating, 5 stars1 month ago
We had never been to the Keys before and were not sure where to stay. Islamorada ended up being an excellent choice. There was a great variety of activities nearby, and within a 30-45 minute drive there were even more unique places to visit. The private community where Gina's house is located feels like a mini-resort that The Mouse would be proud of. The community was clean, the staff were extremely friendly, and the other people we met were all gracious. Gina's house was well located - close to the entrance and a 1-minute walk to the pool. The house was super clean, comfortable, and the few things we had questions about were immediately dealt with by Gina. We're considering another trip to the Keys and would not hesitate to stay here again or recommend it to another group.
Top guest favorite
Villa in Marathon
5 out of 5 average rating, 22 reviews

Indigo Reef water view Villa- #1 Guest Favorite

MarthaRating, 5 stars3 weeks ago
Perfect location in the Middle Keys with easy access to all that Marathon has to offer, Key West or Islamadora. The home is well appointed and the views of the Gulf out the two back porches are spectacular! Very peaceful setting and close to the docks and pool. Would stay here again in a heartbeat!
A sparkling pool is set against a backdrop of lush greenery and calm water. A hammock is suspended between palm trees, inviting relaxation. Surrounding the pool, well-maintained landscaping features vibrant plants and manicured grass, enhancing the serene outdoor space.
Villa in Marathon
4.67 out of 5 average rating, 3 reviews

Villa Sombrero

NikkiRating, 5 stars30 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.
An aerial view captures a curvilinear pool surrounded by palm trees and lounge chairs. The surrounding landscape features pathways and landscaped areas, enhancing the serene atmosphere of the resort. The pool area is complemented by a light-colored deck and nearby structures.
Villa in Key Largo
4.9 out of 5 average rating, 20 reviews

Lux Villa for Spring Break: Pool, Kayak & Marriott

JillRating, 5 stars6 days ago
Beautiful home with amazing access to amenities
Two comfortable white Adirondack chairs are positioned on a wooden deck, overlooking a lush green lawn and palm trees. A canal with a boat can be seen in the background, completing the serene waterfront view.
Villa in Marathon

Luxury Waterfront Villa, Marathon, Florida Keys

ShawnRating, 5 stars5 months ago
Very clean quiet and an excellent pool area!
Villa in Key Largo
4.79 out of 5 average rating, 68 reviews

Oceanfront Villa overlooking the Atlantic

ShannonRating, 5 stars27 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!
Villa in Key Largo
4.85 out of 5 average rating, 46 reviews

2bd/2ba Ocean Retreat in Kawama Yacht Club

JanetRating, 5 stars2 months 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!
Superhost
An aerial view captures a marina community surrounded by lush greenery and clear blue waters. The scene includes multiple townhomes lined along the waterfront, with boat slips visible along the shoreline. A resort-style pool can also be seen in the center of the community.
Villa in Marathon

Refreshed & Elevated Indigo Reef Luxury Villa 15,

HenryRating, 5 stars14 months ago
Beautiful location in the Keys. We loved our stay, and the unit was comfortable, clean and new. Great pool, wonderful dock and pleasant neighbors. Would definitely come back!

Private villa rentals

A serene waterfront scene is depicted, featuring paddle boards laid along a grassy area beside a concrete pathway. Palm trees and a sunset over the water contribute to the natural beauty, while boats are visible in a nearby dock.
Villa in Islamorada
5 out of 5 average rating, 3 reviews

The Nest Villa & Marina in the heart of Islamorada

JoanneRating, 5 stars4 days ago
This was our second stay at The Nest and we will be back! The interior is so soothing, comfortable, clean and very well stocked. Communication with the host was great and they were very responsive to questions. The surroundings are beautiful and peaceful, and the HUGE patio was so perfect for relaxing at the end of the day. Can’t wait to go back!
The living area features a comfortable gray sofa and a patterned armchair surrounding a wooden coffee table. Sliding glass doors provide access to the pool area, allowing natural light to fill the room and offering views of the lush greenery outside.
Villa in Duck Key
4.38 out of 5 average rating, 21 reviews

2BR water view with private pool, balcony & kayak

StefanieRating, 5 stars3 months ago
We overall had an amazing stay! Beautiful views, clean house, & responsive hosts!
Superhost
An aerial view captures a row of white-roofed villas along a turquoise lagoon, surrounded by lush greenery. The serene waters extend towards the horizon, with a distant shoreline visible, creating a tranquil and spacious atmosphere.
Villa in Duck Key
4.83 out of 5 average rating, 78 reviews

Villa 5034 on Duck Key BOAT SLIP available

MeganRating, 5 stars2 months ago
Frank's place was just as listing shows! Perfect location on Duck Key. Beautiful sunsets right on Tom's Harbour. Would recommend to others!
The view from the patio showcases a vibrant sunset reflecting on the tranquil water. Lush palm trees frame the scene, with the illuminated pool area visible below. A distant pier extends into the water, enhancing the serene ambiance of the location.
Villa in Marathon
4.76 out of 5 average rating, 151 reviews

Sunset Villa in Duck Key

MichaelRating, 5 stars1 week ago
Perfect weekend getaway for us at this Duck Key townhouse! The views from the balcony were lovely, the accommodations inside the unit were comfortable and clean, and our host Gabriel was extremely responsive and helful when answering our questions. Would recommend this rental to anyone looking for a great stay in the Keys!
A spacious living area features a comfortable gray sofa with decorative pillows, accompanied by a natural wood coffee table. A large television is mounted on a light wall, while a dining area with white chairs is visible in the background.
Villa in Duck Key
4.83 out of 5 average rating, 104 reviews

Waterfront villa for families * Family friendly*

ShanaRating, 5 stars1 month ago
The place was decorated very cute, it was clean, had all the amenities necessary for a comfortable stay, would definitely book again.
Superhost
A wooden table with round seating is positioned on a covered porch, framed by vibrant tropical landscaping. Lush palm trees and clear blue skies are visible, creating a serene outdoor space. The view extends to a community pool area in the background.
Villa in Duck Key
4.71 out of 5 average rating, 56 reviews

Villa 5086 on Duck Key BOAT SLIP available

EmmaRating, 5 stars2 months ago
Great spot! Frank is very responsive! Highly recommend!
Superhost
A spacious outdoor area is showcased, featuring a covered porch with a ceiling fan. A view of the calm blue water and landscaped greenery is highlighted, presenting a sense of tranquility. The distant horizon features low buildings and sailboats, enhancing the serene coastal atmosphere.
Villa in Duck Key
4.91 out of 5 average rating, 47 reviews

Villa 5028 on Duck Key BOAT SLIP available

EdwardRating, 5 stars2 months ago
This is a great spot. Very quiet and close to everything we wanted to do. The place was spotless and had everything we needed. Frank is very responsive. I highly recommend this place.
A comfortable living area features a gray sofa and a wicker chair, complemented by an orange accent wall. Large sliding doors provide access to an outdoor space, allowing natural light to fill the room. Neutral-toned tile flooring enhances the inviting atmosphere.
Villa in Marathon
4.53 out of 5 average rating, 15 reviews

Key Lime Cottage - Lovely Duck Key Villa, Dip Pool

AlexandraRating, 5 stars6 months ago
Beautiful little townhome on duck key! I had a medical conference, and I walked to it every morning. Very convenient. We would stay again. Our only complaint was that the larger bedroom bed was so uncomfortable. I woke with severe back pain first 2 nights. My husband and I then slept in the twin beds in the other bedroom which were much more comfortable! Other than that, no complaints. It was December, so dipping pool of course was cold, but it would be so nice to have during a summer stay! Quick responses from the owner or manager! We had enough trash bags, toilet paper and paper towels for 2 people for our 6 day stay, which was very nice! Kitchen is fully functional and full size fridge!

Luxury villa rentals

Guest favorite
The exterior of the villa features a welcoming front porch with a ceiling fan and white railings. Lush palm trees and tropical foliage frame the entrance, complemented by light-colored siding and colorful accents.
Villa in Islamorada
5 out of 5 average rating, 6 reviews

Isla Guava: FREE Boat Dockage Sept-Oct Only!

JenRating, 5 stars4 months ago
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!!
A spacious outdoor area features a private pool surrounded by a wooden deck. Loungers invite relaxation under the shade of palm trees. The home, with two stories, showcases a covered patio equipped with dining furniture, complemented by lush greenery for added privacy.
Villa in Duck Key
5 out of 5 average rating, 3 reviews

Florida Keys Sanctuary

VictoriaRating, 5 stars2 weeks ago
I celebrated both my mom’s birthday and mine here, and from the moment I booked until check-out, the experience was nothing short of amazing. The property manager was incredibly helpful, responsive, and made everything seamless. Highly recommend!
Guest favorite
The two-story villa presents a light green exterior with multiple large windows, allowing natural light to enter. Elevated on stilts, ample space underneath offers shade, while the stairway leads to the main entrance. Architectural details emphasize a welcoming coastal style.
Villa in Marathon
4.88 out of 5 average rating, 58 reviews

New Paradise On Sombrero Beach

JenniRating, 5 stars1 month ago
The house was well equipped with all of the essentials. We had 8 adults and plenty of room. We did have to wash towels a few times, and buy more laundry soap, but the washer and dryer were conveniently located on the main level. The pool was smaller than what the pictures showed, but it perfectly suited our needs. All members of our party viewed the listing before we booked it and none of us realized it was a twin home. However, there is tons of privacy and the only times we noticed we had neighbors was when the shared dock was used. We had to buy a cooler (for poolside and the beach) and beach chairs. There were some pool floaters left behind, from previous guests that we used. The interior of the home is beautiful, with high ceilings and comfortable furniture. This is in a great location - close to grocery stores, restaurants and Sombrero beach! Monica was great to work with!
Guest favorite
A covered porch features four white Adirondack chairs positioned on a wooden deck. Lush green palm trees and landscaping provide a tropical backdrop, while a sparkling pool is visible in the distance, completing the serene outdoor setting.
Villa in Marathon
5 out of 5 average rating, 10 reviews

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

KatrinRating, 5 stars2 months 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!!
Superhost
Aerial view of the Indigo Reef gated community, showcasing rows of villas surrounded by lush greenery. Crystal-clear waters are visible, with docks leading to the ocean. The vibrant blue sky extends over the scene, reflecting the peaceful coastal environment.
Villa in Marathon
5 out of 5 average rating, 10 reviews

Marlin House (52): Luxury 3/3 Villa w/ Dock, Pool

PaigeRating, 5 stars6 days ago
The waterfront townhome was the PERFECT place for our family of 8! Four kids shared one room with four beds-our kids loved that they were together. We always have dinner together after our daily outings and the kitchen and table worked out great. We LOVED the outdoor space in the backyard! Watching the boats, the sunset and kids playing and fishing. We can't tell you how much we enjoyed outselves and we do hope we are able to come back again!
A spacious outdoor area features a large swimming pool with an integrated hot tub, surrounded by a tiled deck. Lounge chairs and seating arrangements are visible, with palm trees providing natural shade. The property showcases a well-lit, modern architecture complemented by large windows.
Villa in Marathon
4.8 out of 5 average rating, 25 reviews

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

EdithRating, 5 stars4 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 favorite
A private pool with a curvy shape is surrounded by a spacious patio featuring lounge chairs in light green. Lush greenery frames the area, and a shared dock with a boat is visible in the background, offering access to the canal.
Villa in Marathon
4.96 out of 5 average rating, 27 reviews

Discount Available! 4BR/3BA! Many Extra Amenities!

KathieRating, 5 stars4 months ago
The place was perfect for our group of 9. We enjoyed the pool and the view. The kitchen was very well stocked as we cooked most of the time. Loved the outside sitting area with the TV. So glad we found this place!
An outdoor pool is surrounded by lounge chairs under palm trees, with the tranquil water reflecting the evening sky. The setting sun casts a soft light, enhancing the serene atmosphere of the pool area, which overlooks the bay.
Villa in Islamorada
4.71 out of 5 average rating, 7 reviews

Scenic Resort w/ Outdoor Pool | Florida Keys Stay

JackieRating, 5 stars3 months ago
Very nice townhouse, it was also really convenient to call the golf cart and go to the larger resort, which was beautiful.

Quick stats about villa rentals in Key West

  • Total rentals

    10 properties

  • Nightly prices starting at

    ﺩ.ﺇ881 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

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  4. Monroe County
  5. Key West
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