Villa vacation rentals in Key West

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Popular amenities for Key West villa rentals

Villa rentals with a pool

Top guest favorite
A serene pool area features a heated swimming pool with lounge chairs arranged nearby. A tiki hut stands at the edge, with vibrant sunset colors reflected on the water's surface, framed by lush palm trees.
Villa in Islamorada
5 out of 5 average rating, 7 reviews

Isla Key Lime: FREE Boat Dockage Sept-Oct Only!

Ricky Rating, 5 stars1 month ago
Key Lime Villa & Newman Hospitality were all around fantastic! We really enjoyed our weeklong stay at this beautiful property! They were a great host, very helpful and easy to deal with, super responsive too. The property itself was just as described, very nice, spacious and squeaky clean, very comfortable, we were able to settle in right away. Being big dog friendly was really nice as well, our boys were very comfortable and really enjoyed the place. We really love the pool and the fire pit area along with the dock area for sunset, it was very peaceful. Also, the location is perfect, it was right in the heart of the island so we were able to do a ton of walking to all of our restaurants and bars. We will definitely be back to stay here again for another trip soon! Thanks again to the team at Newman for making our stay a great one!
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 pool area is highlighted by lounge chairs arranged around the water. A large tiki hut provides shade, while palm trees sway nearby. The scene is complemented by a colorful sunset sky, casting soft hues over the tranquil setting.
Villa in Islamorada
5 out of 5 average rating, 3 reviews

Isla Kiwi: FREE Boat Dockage Sep-Oct Only!

KellyRating, 5 stars7 months ago
Our first time staying here. Beautiful place close to all things around islamorada. Can walk pretty much anywhere. Great pool and grounds.
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 stars1 week 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!
An aerial view of a beautiful villa surrounded by lush greenery and palm trees. The property includes a private heated pool, lounge chairs, and a tiki hut, all set against the tranquil waterfront, with a boat dock visible along the edge of the water.
Villa in Islamorada
4.86 out of 5 average rating, 7 reviews

3 EnSuite Bedrooms,FREE boat dockage Sept-Oct only

MeghanRating, 5 stars2 months 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!
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!
Top guest favorite
A private swimming pool is surrounded by a wooden deck and tropical landscaping, featuring palm trees for shade. Lounge chairs are positioned near the pool, while the two-story home with a covered balcony overlooks the serene outdoor space.
Villa in Duck Key
5 out of 5 average rating, 72 reviews

Duck Key *Bliss* Private Pool & Patio

JamieRating, 5 stars1 month ago
We enjoyed all the little extra touches around the house also loved the privacy of the back yard with the pool.We would definitely stay here again
Villa in Islamorada
4.67 out of 5 average rating, 51 reviews

Picturesque Villa Near History of Diving Museum

ElizabethRating, 5 stars1 month ago
Beautiful place on Islamorada halfway between Key West and Fort Lauderdale...so peaceful and great views... the heated pool was also very nice... the Lavazza coffee maker made our morning since its not really a place you can walk to/from... there is a flight of stairs just in case you have mobility issues... bathroom amenities are very nice!

Beachfront villa rentals

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!
Top guest favorite
A charming two-story villa is framed by swaying palm trees against a bright blue sky. Lush greenery borders the pathway leading to the entrance, which features a porch with round windows and white railings, emphasizing the inviting exterior of the residence.
Villa in Marathon
5 out of 5 average rating, 20 reviews

Seas the Keys Getaway

NatalieRating, 5 stars1 week ago
We have been going to Hawks Cay for over 10 years now and have stayed in the resort and many of the townhomes. Carmen‘s place is so peaceful, clean and nicely decorated you feel right at home. Our favorite part was the little pool on the patio overlooking the water. Best part of coming back home from a long day on the boat and taking a dip!
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!
A large heated pool is set against a serene backyard, featuring a cascading hot tub and an outdoor seating area. Light reflects off the water's surface, while comfortable loungers are positioned along the pool's edge. A modern building is visible in the background, adding to the overall charm.
Villa in Marathon

Waterfront Villa: Serene Escape!

AmyRating, 5 stars2 months ago
This was our first trip to the keys, and Marathon is the perfect home base. We had 6 people in our group, 4 teens and 2 adults and this home was absolutely perfect for our family. We loved the canal location and spent the mornings driving coffee while boats moved in and out. The pool was absolutely perfect and we didn't a lot of time, morning, noon and night enjoying the pool. Sleeping arrangements are great, plenty of beds for the whole crew. The house does not beach supplies, so make sure if that's on your list, you grab towels, cart, cooler. Sombrero beach is close and one of the nicest in the keys. The neighborhood is quiet, lots of other rentals, and felt very safe. This home is nicely decorated and the kitchen is big and spacious. We would love to come back tomorrow!!
A private pool is surrounded by a paved patio, featuring comfortable lounge chairs and large umbrellas for shade. Nearby, a hammock is suspended between two posts, and tropical greenery provides a natural backdrop. The area is well-lit by natural sunlight.
Villa in Marathon

"Keepin’ It Reel" Waterfront, 4BD/3BA FL Keys Home

DanteRating, 5 stars2 months ago
The home and the location and the dock are all fantastic. The home is at the end of the channel so it takes a bit to get to, but you also don't have traffic so your boat is secure and not subject to other wakes, and there were a lot of iguanas which was really cool! The home is very well appointed and luxurious and also close to the main road so its easy to get to Publix and local restaurants. It also has all the pots and pans you could need. The master bedroom is spacious and has a nice bathroom and the sunset from the master is incredible. I highly recommend this property, 10/10 would absolutely rent it again! The ice machine was a really nice touch, it gave me enough ice for the cooler and the boat cooler every morning! Access to the Atlantic via boat takes about 20 minute and access to the Gulf via boat takes about 25 minutes.
Guest favorite
A two-story house with a light-colored exterior overlooks a serene canal. A spacious deck with turquoise lounge chairs surrounds a clear pool. Tiki huts provide shaded seating, while palm trees add to the tropical ambiance. Large glass doors open to the indoor living area.
Villa in Islamorada
4.98 out of 5 average rating, 47 reviews

luxury & fishing bigdavechartersandtours.comm -1m

ToddRating, 5 stars4 weeks ago
Greta host !!! Great place !! Would absolutely stay here again !!!!! The pool is awesome!!! Very clean !!!
Guest favorite
An outdoor lounge area features a private spa pool surrounded by tropical plants and seating. Soft lighting creates a welcoming atmosphere, while the vibrant sunset sky adds a colorful backdrop. Sliding doors connect the space to the interior of the villa.
Villa in Marathon
4.89 out of 5 average rating, 94 reviews

Villa in Paradise. Plunge pool. Middle of the Keys

CrystalRating, 5 stars1 month ago
The place certainly served its purpose for our short stay in the Keys. We didn’t spend a lot of time in the unit but when we were there it was quiet and private. The plunge pool was nice after a long hot walk. You cannot get direct access to the dock to walk near the unit as it has been cut off from walking so you do need to walk a bit to the other units closer to the entrance to gain access to walk. The basics were provided for a first night there (eg tiny shampoo and soap) so you certainly need to bring your own supplies. The place was clean and quiet and a good location 1/2 down the keys which was perfect for us.
Guest favorite
A shaded outdoor dining space features a wooden table set for two, overlooking the water. Views of boats are visible in the distance, with a clear blue sky reflecting on the water's surface. The area is well-maintained, creating a calm and inviting setting.
Villa in Cudjoe Key
4.95 out of 5 average rating, 21 reviews

Howard House on the Sea

LyndaRating, 5 stars2 weeks ago
Such a lovely place right on the water with awesome views. The house looked even better than the pictures. It was decorated nicely with family style accommodations. The house is updated beautifully and kitchen stocked nicely and felt like a home not a vacation rental. Seating around the dock area and upper deck was so nice and comfortable. Snorkeling along the area was enjoyable but you do need to be cautions of the local boats that come through the channel area. The host was very friendly and responsive and left a welcome gift packet of some basic needs to start our vacation. We look forward to returning for another vacation.

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

The Nest Villa & Marina in the heart of Islamorada

Christy & MatthewRating, 5 stars7 months ago
An amazing place! The pictures don’t do it justice and Gary was an amazing host as well! We plan to stay again in the future!
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!
A spacious bedroom features a king bed with crisp linens and a decorative pillow. Large glass doors open to a private patio, allowing natural light to fill the room. A ceiling fan provides air circulation, and a flat-screen TV is positioned on a light-colored media console.
Villa in Islamorada
5 out of 5 average rating, 3 reviews

2 Spacious Villa Perfect For Family Beach Retreat

LanceRating, 5 stars6 months ago
All was great and as expected! Would stay again! Beautiful views.
A bright living area is furnished with a gray sofa and a wooden coffee table, featuring decorative elements. A wall-mounted smart TV is visible, alongside a light fixture and a dining area in the background. Natural light enters through plantation shutters, enhancing the spaciousness.
Villa in Duck Key
4.73 out of 5 average rating, 64 reviews

Family Friendly Sunset Oasis!

JoyceRating, 5 stars1 month ago
Loved the Villa and its location. Host was excellent. A bit disappointed that we were not permitted to use the beautiful pool just behind the Villa. Also, second bedroom is very small (cannot tell from in-line photos) and while twin beds would serve children well, they are not suitable for adults.
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!

Quick stats about villa rentals in Key West

  • Total rentals

    10 properties

  • Nightly prices starting at

    G$50,361 GYD 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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