Holiday rentals with a pool in Key Haven, Key West
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Key Haven, Key West
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Key Haven, Key West rentals with a pool
House rentals with a pool
Home in Marathon
5 out of 5 average rating, 7 reviewsBeachy & Bright - 3 BR, Private yard, Heated pool
Beautiful 2nd story home with plenty of seating, adequate room for 6 guests if needed, with every kitchen convenience you could imagine. Spent days relaxing in the pool when not out enjoying activities in the ocean. Neighborhood was relatively quiet and backyard pool area felt secluded and enjoyable. Could hear occasional airplanes coming and going from nearby airport but it was not a bother. Read several books during our stay while we basked in the sun. All items in home were in excellent working order. Spent a couple of days in Key West which was a beautiful drive and only took a little over an hour. Highly recommended accommodations!
Home in Marathon
5 out of 5 average rating, 12 reviewsWaterfront Oasis w/Private Pool-Dockage-Beach
Incredible property. Perfect gathering space for my entire family of 6. Private yet close to commerce like Publix and local gym to work out. Great memories made.
Home in Marathon
4.76 out of 5 average rating, 17 reviewsCasa Playa~ Luxury Pool
We had a great time! House was beautiful and set up perfect for a relaxing week. Pool, pool area, and dock is were we spent most of our time. Kayaks and paddleboards were a nice treat to just simply paddle out of the canal and into the Atlantic shallows. This house has lots of space, we never felt like we were on top of each other. Any issues/concerns that we had were communicated and addressed promptly. Beds were comfortable which is very important to us. Poor sleep equals a bad week. Another important thing for us is the shower. Showers were clean and had great water pressure. Kitchen had everything needed to cook full meals. We used the stove, oven and grill everyday. We look forward to visiting again soon!
Home in Key West
5 out of 5 average rating, 22 reviewsCatherine House: A charming Old Town Key West
We’ve stayed at Catherine House 2 years in a row and have loved it! I walked around a lot and the location of Catherine House is wonderful. So close to shops, galleries and restaurants. I love the bed linens and towels. Very luxurious. We cooked in and had everything we needed to do so. We thank you for all that has been done to make us want to stay at Catherine House again.
Home in Key Colony Beach
4.83 out of 5 average rating, 12 reviewsP22 - Updated 3 bedroom 2 bath duplex with private
We had six adults in our group and the house was a perfect location to go out fishing or to the beach. The house was well stocked and with plenty of linens and beach towels. We rented a boat for three days from Tropical boat rentals and the canal location made fishing super easy. Access to the ocean or the bay was convenient. We even caught several fish in the canal. We saw manatees, sharks, manna rays and tons of fish while enjoying the swimming pool. We can’t wait to make a return trip.
Home in Key West
5 out of 5 average rating, 7 reviewsCasablanca ~ Fabulous Home w/ Private Pool/Parking
We loved our time here. We walked everywhere . We loved having the pool - perfect in the afternoons before we went back out for dinner . Would absolutely stay here again !
Home in Marathon
4.72 out of 5 average rating, 54 reviewsGorgeous 3/2 SFH Brand-new pool&spa, 30ft dockage
Definitely would stay again. Beautiful back yard with the heated pool & spa that we used several times a day/eve. It was a perfect location for the areas we knew we wanted to go. Great restaurants.
Home in Marathon
4.95 out of 5 average rating, 41 reviews🏝BEAUTIFUL🏖WATER VIEW🌅POOL🏊♀️GYM🏋️Room Private⛵️Dock⚓️
Finally, an Airbnb that lives up to its description. Beautiful modern kitchen with everywhere needed. Great location! Made use of the kayaks and paddle boards. Definitely will return next year.
Condo rentals with a pool
Condo in Key Colony Beach
4.74 out of 5 average rating, 151 reviews2 Bedroom Oceanfront Complex Heated Pool KCB
Anne is a very very friendly host. She made us feel like at home. Thank you, Anne for your recommendations! We did just few of them due to a short stay. We will come back again and exlore more!
Condo in Key West
4.68 out of 5 average rating, 80 reviewsBOOK today and enjoy our amazing discounts for yo
We stayed at Julia’s place with a total of 6 people (3 couples) for 4 days. There is plenty of space and we loved the huge kitchen and balcony porch! It was very homey and what you would expect from an older beach condo. The pullout couch is a little aged and not the most comfortable but we made it work. Gorgeous grounds and pool/beach access. Lots of towels and beach towels available and even did a couple loads of laundry while we were there. Walkable to several spots and Ubers were super easy/cheap! Highly recommend the corner sandwich shop/corner store right down the street for amazing Cubans and quick groceries. Can’t wait to go back!
Condo in Key West
4.94 out of 5 average rating, 35 reviewsCondo de Paradise/Salt Water Pool/Boat Dock
Peaceful location just a short drive to Key West. The views were beautiful and the condo was just like the pictures! Very spacious and comfortable with everything you'd need. It was the perfect space for our family of four. Cynthia was great. Very responsive and friendly!
Condo in Key West
4.98 out of 5 average rating, 64 reviewsOceanfront 3 bed condo Ocean Edge w/ optional slip
Absolutely stunning view and glorious place to stay. Carrie has thought of everything - and we felt truly at home. Such comfortable beds, spacious bedrooms and kitchen/living areas. And the designated parking space was a plus! We really hope to return in the future.
Condo in Key West
4.73 out of 5 average rating, 91 reviewsTop floor Ocean Views, Spacious 2 Bedroom Condo, V
great place to stay in key West!
Condo in Key West
4.89 out of 5 average rating, 122 reviewsTropical Escape at Sunrise
My parents and I stayed at Eric’s lovely unit in Key West. The residence had lots of amenities and a walkable grocery store. The location was perfect to visit all the things Key West had to offer.
Condo in Key West
4.77 out of 5 average rating, 98 reviewsPool View Suite | Beachside Resort
This was the perfect weekend getaway spot for my boyfriend and I. Only a few minutes drive away via complimentary shuttle to all of the downtown attractions, bars, and restaurants. The accommodations were beautiful, quiet, comfortable and plenty spacious with a great balcony for morning coffee, while listening to the tunes playing down below. All of the staff we encountered on the property were friendly, and accommodating. My only complaint, was that the water pressure in the shower was really horrible (but honestly just a minor glitch in an otherwise fantastic stay).
Condo in Key West
4.95 out of 5 average rating, 128 reviewsFully renovated 2/2 bath condo w/ shared pool!
Place was clean and exactly as pictured. The location was a little away from the main shopping area but we liked the beautiful view of the sunset from the deck. This property is located very close to the airport, and we did hear the planes, However most of the flights leave during waking hours so it was fine. Overall we had an excellent experience and would recommend it highly. Thank you Chris Well done Kathleen
Quick stats about holiday rentals with a pool in Key Haven, Key West
Total rentals
70 properties
Nightly prices starting at
$177 AUD before taxes and fees
Total number of reviews
920 reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Destinations to explore
- Key West Holiday rentals
- Florida Keys Holiday rentals
- Havana Holiday rentals
- Miami Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Bay Holiday rentals
- St Petersburg Holiday rentals
- Tampa Holiday rentals
- Central Florida Holiday rentals
- Kissimmee Holiday rentals
- Rentals with pools United States
- Rentals with pools Florida
- Rentals with pools Key West
- Rentals with pools Miami-Dade County
- Rentals with pools Florida Keys
- Rentals with pools Monroe County
- Fitness-friendly rentals Key Haven
- Family-friendly rentals Key Haven
- House rentals Key Haven
- Rentals with outdoor seating Key Haven
- Rentals with a washing machine and dryer Key Haven
- Rentals with a patio Key Haven
- Pet-friendly rentals Key Haven
- Monthly Rentals Key Haven
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom