Holiday rentals with a pool in Key Haven, Key West

Find and book unique homes with a pool on Airbnb

When results are available, navigate with up and down arrow keys or explore by touch or swipe gestures.
0 of 0 items showing
1 of 3 pages

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

House rentals with a pool

Superhost

Home in Marathon

5 out of 5 average rating, 7 reviews

Beachy & Bright - 3 BR, Private yard, Heated pool

RachelleRating, 5 stars6 months ago
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!
Guest favourite

Home in Marathon

5 out of 5 average rating, 12 reviews

Waterfront Oasis w/Private Pool-Dockage-Beach

DaveRating, 5 stars1 month ago
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.
Superhost

Home in Marathon

4.76 out of 5 average rating, 17 reviews

Casa Playa~ Luxury Pool

JenniferRating, 5 stars7 months ago
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!
Guest favourite

Home in Key West

5 out of 5 average rating, 22 reviews

Catherine House: A charming Old Town Key West

SusieRating, 5 stars3 months ago
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.
Superhost

Home in Key Colony Beach

4.83 out of 5 average rating, 12 reviews

P22 - Updated 3 bedroom 2 bath duplex with private

BrittanyRating, 5 stars28 months ago
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.
Superhost

Home in Key West

5 out of 5 average rating, 7 reviews

Casablanca ~ Fabulous Home w/ Private Pool/Parking

AshleyRating, 5 stars21 months ago
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 !
Superhost

Home in Marathon

4.72 out of 5 average rating, 54 reviews

Gorgeous 3/2 SFH Brand-new pool&spa, 30ft dockage

AlyciaRating, 5 stars1 month ago
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.
Guest favourite

Home in Marathon

4.95 out of 5 average rating, 41 reviews

🏝BEAUTIFUL🏖WATER VIEW🌅POOL🏊‍♀️GYM🏋️Room Private⛵️Dock⚓️

LennyRating, 5 stars1 month ago
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

Superhost

Condo in Key Colony Beach

4.74 out of 5 average rating, 151 reviews

2 Bedroom Oceanfront Complex Heated Pool KCB

KamilRating, 5 stars1 month ago
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!
Superhost

Condo in Key West

4.68 out of 5 average rating, 80 reviews

BOOK today and enjoy our amazing discounts for yo

MadisonRating, 5 stars3 months ago
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!
Guest favourite

Condo in Key West

4.94 out of 5 average rating, 35 reviews

Condo de Paradise/Salt Water Pool/Boat Dock

ErinRating, 5 stars4 weeks ago
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!
Guest favourite

Condo in Key West

4.98 out of 5 average rating, 64 reviews

Oceanfront 3 bed condo Ocean Edge w/ optional slip

BarbaraRating, 5 stars3 weeks ago
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.
Superhost

Condo in Key West

4.73 out of 5 average rating, 91 reviews

Top floor Ocean Views, Spacious 2 Bedroom Condo, V

ChrisRating, 5 stars1 month ago
great place to stay in key West!
Guest favourite

Condo in Key West

4.89 out of 5 average rating, 122 reviews

Tropical Escape at Sunrise

ShiqinRating, 5 stars2 days ago
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.
Superhost

Condo in Key West

4.77 out of 5 average rating, 98 reviews

Pool View Suite | Beachside Resort

HeatherRating, 5 stars5 days ago
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).
Guest favourite

Condo in Key West

4.95 out of 5 average rating, 128 reviews

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

KathleenRating, 5 stars6 days ago
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

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