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Vacation rentals with a pool in Key Haven, Key West

Find and book unique homes with a pool on Airbnb

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Popular amenities for Key Haven, Key West rentals with a pool

House rentals with a pool

Superhost
A well-maintained community pool is surrounded by lush tropical landscaping, featuring lounge chairs with blue umbrellas. The clear water reflects the bright blue sky and palm trees, creating a relaxing atmosphere for guests to enjoy.
Home in Key West
4.86 out of 5 average rating, 59 reviews

Key West Paradise

BharatRating, 5 stars2 weeks ago
Sharon was an excellent host that answered any of our questions promptly. The place was even better than what the photos showed. Comfortable enough for 7 people to stay for a long weekend. We didn't use the pool, but it was nice to have the option. Easy to get into the gated community, and we didn't struggle to find parking with our rental car. Easy to get to many different popular spots around Key West with rideshare. Convenient to have some convenience stores like CVS within walking distance, and a Publix not too far via car. Only thing I would improve is having more toilet paper and hand soap refills in each bathroom, especially with 7 people staying over a long weekend.
Guest favorite
Home in Key West
4.92 out of 5 average rating, 283 reviews

Family House, 2 K BR's, Private Spa/Deck, 2 pools.

StedmanRating, 5 stars4 days ago
We loved our stay and will definitely recommend to friends and family. Hope to return someday soon!
Top guest favorite
A private pool is surrounded by a paved patio, featuring lounge chairs and a small table. Lush tropical plants provide a natural backdrop. In the distance, a boat dock is visible along with outdoor dining furniture and an umbrella. Soft lighting enhances the inviting outdoor space.
Home in Marathon
5 out of 5 average rating, 14 reviews

Waterfront home w/pool, dock & close to beach

LaurenRating, 5 stars1 month ago
We did a couples’ trip with our three toddlers and had a wonderful stay at Ruth’s place! We had everything we needed and the location was awesome - close to beautiful Sombrero beach, restaurants, nightlife and had a dock where we could dock our rental boat. Would come back in a heartbeat!
Superhost
A private pool glistens under the sun, surrounded by a spacious deck. Several lounge chairs are positioned nearby for relaxation. In the background, a tiki palapa with a thatched roof offers shaded seating, complemented by lush tropical foliage and a distant pink house.
Home in Summerland Key
4.88 out of 5 average rating, 34 reviews

Pelico Palms Sunset Suites

TimRating, 5 stars1 week ago
fantastic cottage and pool with plenty of privacy, close to the water. basically 3 master suites with adjoining bathrooms, one living area and a kitchen. really big pool deck with seating and cornhole, Webber grill and outdoor dining table. (bring bug spray). we had a great time, close to key West and Bahia Honda, a great cottage!
Superhost
This aerial view captures a canal front home, showcasing two private pools on the lawn and a dock for boat access. The surrounding greenery complements the spacious outdoor areas, while the coastal setting is highlighted by the water's edge.
Home in Marathon
4.95 out of 5 average rating, 22 reviews

Get Hooked private pool and dock

LynnRating, 5 stars2 weeks ago
We recently had the pleasure of staying at a fantastic vacation rental, and it exceeded all our expectations! The house was comfortable, spacious, and perfectly equipped for a peaceful and relaxing stay. One of the highlights was the location—just a short and scenic walk to the beach, making it easy to enjoy the sound of the waves and the coastal vibe. We were also treated to the most beautiful sunrises each morning, a sight that truly made the experience unforgettable. The home was spotlessly clean, with thoughtful details that made us feel at ease. And Sheri, the host, was incredibly friendly and welcoming, ensuring every part of our stay was smooth and enjoyable. Her kindness added an individualized touch to the experience. If you’re looking for a perfect getaway with stunning views, a cozy atmosphere, and a host who genuinely cares, this place is absolutely worth considering!
Guest favorite
A private backyard features a newly renovated pool and spa combo, surrounded by a concrete patio. The stilted house above is complemented by a spacious screened-in porch with teal seating. Lush greenery enhances the tropical ambiance of the outdoor space.
Home in Marathon
4.97 out of 5 average rating, 35 reviews

Marathon 3BR Canal Pool Spa Special WK May 4-11

MattRating, 5 stars2 days ago
Great peaceful place to stay. We saw manatees, tarpon and many other species in the canal. Also had some short visits from different types of lizards and iguanas. The pool and hot tub were amazing everyone in our group enjoyed them. The dock was a great place to keep our rental boat. I would 100% come back.
Superhost
A private pool area is surrounded by tropical landscaping, featuring lush greenery. Several lounge chairs with blue and white stripes are positioned around the pool, inviting relaxation. Bright sunshine casts light across the tranquil water, enhancing the peaceful outdoor setting.
Home in Key West
5 out of 5 average rating, 9 reviews

Casablanca ~ Fabulous Home w/ Private Pool/Parking

KathleenRating, 5 stars2 months ago
The house is perfect! It’s very clean and has everything you need. The kitchen is fully stocked with plates, glasses, etc. The bathroom had a nice shower and plenty of towels. We love the location! We parked our car and never used it. You can walk everywhere. The backyard is amazing. The pool is beautiful. We swam every day and loved sitting in the yard relaxing. We will be back.
Guest favorite
An outdoor space features a large swimming pool surrounded by a well-maintained lawn. Lounge chairs are arranged nearby, and a dining set is positioned under an umbrella. A gazebo is visible in the background, contributing to the area’s recreational atmosphere.
Home in Marathon
5 out of 5 average rating, 10 reviews

Sunset keys villa w/Den, pool, Firepit &Boat space

MichelleRating, 5 stars4 weeks ago
Everything about Lazaro’s stay was 5 Star!! He was easy and friendly to communicate with and went above and beyond to make our stay a delight. The property itself was perfect. Everything is brand new and it was one of the best stocked places I have stayed, from the decor to the spacious layout to the stocked cabinets. The fully fenced yard was perfect for our dogs who enjoyed it very much. The location is on a quiet street in the heart of Marathon with so much close by. Ideal!! Truly a 5 star stay and highly recommended.

Condo rentals with a pool

Guest favorite
A spacious outdoor patio is viewed, featuring a dark wooden table and black wicker chairs. A decorative rope centerpiece is placed on the table. The horizon displays a vivid sunset with shades of orange, pink, and purple, casting a serene reflection over the calm water.
Condo in Key West
4.97 out of 5 average rating, 73 reviews

Oceanfront 3 bed condo Ocean Edge w/ optional slip

LesleyRating, 5 stars2 weeks ago
Carrie's place was absolutely beautiful! it was so clean, the beds were insanely comfortable, and there were tons of linens and towels for everyone. We very comfortably fit 8 people into the home with no problems. The view from the balcony is absolutely amazing and we were all blown away. Carrie was extremely responsive and friendly. We were here for our wedding and had our wedding party stay here so it was extra magical. The pool and hot tub is super close, elevator to help with our bags, and the resort itself is gorgeous. 10/10 would stay again. We loved it so so much! Don't miss out.
Superhost
A resort-style pool area is featured, surrounded by palm trees and lounge chairs. Shade is provided by large umbrellas over the seating. The pool surface reflects the clear blue sky, creating a serene and inviting environment for relaxation.
Condo in Marathon
5 out of 5 average rating, 3 reviews

Beach/Docks Avail/3 Pools/Hot tub/Gym/Restaurants

MichaelneuroRating, 5 stars3 months ago
Great experience, great host and accommodations. Hot tub wasn't working while we were there, but repair was delayed over the holiday week which was out of the hosts' control. Very communicative and responsive.
Superhost
A panoramic view showcases the tranquil ocean, framed by palm trees and lush greenery. The scene captures a clear blue sky and the vibrant color of the water, with the outline of nearby buildings visible in the backdrop.
Condo in Key West
4.73 out of 5 average rating, 94 reviews

Top floor Ocean Views, Spacious 2 Bedroom Condo, V

JudyRating, 5 stars1 month ago
This was our first time in Key West. We wanted to stay a little tucked away from the downtown bustle. The complex is beautiful with great amenities. And it’s close enough to shopping, restaurants and bars! We definitely plan on booking the same place in the future!!
Superhost
A serene ocean view is captured, showcasing the calm turquoise waters and distant boats. Lush palm trees frame the scene, while a community pool and sandy beach are visible below, inviting relaxation in a tranquil, tropical setting.
Condo in Key West
4.84 out of 5 average rating, 154 reviews

Anchor Drop modern elegance upgrades throughout vi

SamanthaRating, 5 stars5 months ago
We loved everything about this place. It was super clean and fresh. The bedding was very comfortable and felt expensive. We drank coffee on the balcony every morning watching the ocean. The oceanfront pool area was clean and well taken care of. The unit was stocked and well labeled with all that we would need and more. The garage door opener for inside private parking was amazing. We watched the Tyson fight in the living room on the BIG tv! Had a great vacation. Thank you.
Superhost
A spacious balcony features a table and four chairs, surrounded by tropical plants. Comfortable seating options are positioned for relaxation, offering views of the calm water and a vibrant sunset in the background.
Condo in Key West
4.75 out of 5 average rating, 4 reviews

Promenade to Paradise at The Annex

AlanRating, 5 stars58 months ago
Absolutely fantastic unit and location, and the communication and service from Last Key was white glove. Top notch. We will be back.
Guest favorite
A spacious outdoor pool area is surrounded by lush greenery and palm trees. Lounge chairs are positioned around the pool, reflecting a serene atmosphere. A shaded gazebo offers a relaxing spot nearby, while the clear water invites refreshment under the bright sky.
Condo in Key West
4.94 out of 5 average rating, 143 reviews

Fully renovated 2/2 bath condo w/ shared pool!

YinanRating, 5 stars1 week ago
We had a great stay at Chris’s place in Key West! The property was exactly what we needed for a relaxing getaway. Chris is an excellent communicator—his instructions were clear, detailed, and made everything super easy from check-in to check-out. We felt well taken care of and really appreciated the smooth experience. I’d definitely recommend this place to anyone planning a trip to Key West!
Guest favorite
A spacious balcony view reveals a heated pool surrounded by lounge chairs. Tiki huts are visible nearby, alongside the boat slips and palm trees, set against a clear blue sky, showcasing a relaxing outdoor space for guests.
Condo in Key West
4.88 out of 5 average rating, 146 reviews

Downtown Key West 2BR/2BA•Pool, Dock, Pet "Aruba"

ThomasRating, 5 stars3 months ago
Die Lage war unschlagbar! In 10 Minuten ist man zu Fuß an der Duval Street! Der kleine Pool ist sehr gepflegt. Für uns als 6-köpfige Familie war es eine sehr tolle Unterkunft auf unserem Roadtrip!
Top guest favorite
Aerial view showcasing a waterfront property bordered by vibrant green mangroves. The calm turquoise water reflects the blue sky dotted with white clouds. A marina with docked boats is visible nearby, creating a serene coastal landscape.
Condo in Key West
5 out of 5 average rating, 87 reviews

Gorgeous Ocean View in Paradise

NickRating, 5 stars2 weeks ago
Mike was great and communicative the whole time leading up to the stay. The place was great. I would totally stay again.

Quick stats about vacation rentals with a pool in Key Haven, Key West

  • Total rentals

    70 properties

  • Nightly prices starting at

    ﺩ.ﺇ331 before taxes and fees

  • Total number of reviews

    990 reviews

  • Family-friendly rentals

    70 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Key West
  6. Key Haven
  7. Rentals with pools