The Sunshine State is packed with breathtaking destinations for outdoor enthusiasts, and one of the best of them is the island of Key West. Part of Florida’s archipelagic region, Key West excites nature lovers with gorgeous beaches and subtropical greenery. Smathers Beach, Fort Zachary Taylor Historic State Park Beach, and Higgs Memorial Beach Park, are among the many pristine beaches that this place offers. Once you’ve enjoyed your dose of beachside fun, you can spend the rest of your day diving into the city’s culture, shopping, and gastronomy scene at Duval Street. Cap off the night with some dancing and drinks at the long-running Sloppy Joe’s. Are you all set for your visit? To get an idea about where you can stay to maximize your vacation experience, browse through this list of the best vacation rentals with private pool in Key West, Florida.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to private pool. The image galleries get refreshed with the latest updates regularly. They were last updated on April 12, 2024.
1. Casa Amor (from USD 677)
Suitable for big groups, this three-bedroom accommodation has enough room for all the members of the family, including fur babies. It boasts a tastefully curated interior, with a kitchen that the chef of the group will surely love. While the indoor facilities of this WiFi-ready Airbnb are impressive, nothing beats what awaits outdoors.
The guesthouse opens onto a lush private pool area, reminiscent of Instagram-worthy tropical retreats. It showcases a waterfall feature for an added flair. During the winter months, guests can have the pool heated.
Top guest reviews
Amenities & Room:
the pool deck was nice and privatepool area can get slippery so a bath mat for the doorway would be saferthe house was spacious and accommodating with a beautiful lanai and pool areaCleanliness:
thanks again to shana
the house was impeccably cleanHost:
propert manager was very responsive to questionsrating details: the property manager was very helpfulrating details: the property manager was very helpfulrating details: the property manager was very helpfulrating details: the property manager was very helpfulRead more reviewsLocation:
ideally located within walking or biking distance to just about everythingthe location was perfect for our familyit’s location is great being within walking distance to everything whether it be the beach or duval streetplenty of room and a great locationi highly recommend this location
2. Bahama House (from USD 654)
If a private pool is a must-have for your ideal Key West vacation rental, this Pinterest-worthy cottage might pique your interest. It has a lovely outdoor pool, shaded by lush vegetation. Colorful pool toys are available for that perfect Instagram snap. Chic sunbeds line one side of the pool, providing guests another picture-perfect spot to relax while savoring a glass of mojito.
This Airbnb is sure to excite art enthusiasts with its artsy pastel-colored aesthetics. Besides being pretty, it is also conveniently furnished with everything one will need for a comfortable stay, including kitchen and laundry amenities.
Top guest reviews
Amenities & Room:
nice little house with a cozy backyard poolCleanliness:
clean and spacious for 6 adultsoverall quite cleancomfortable and clean accommodationsclean and great locationHost:
beautiful home and friendly stayRead more reviewsLocation:
the location of the house is perfectgreat location to good restaurants shopping and entertainmentgreat location just off duval but quietgreat location and perfect little houseshort walk to beach or great restaurants and not too far to walk to the tourist spots
3. Amelia Home (from USD 704)
Of all the things to love about this Airbnb, one thing stands out - the swimming pool. This accommodation is suitable for families, including pets. It assures guests a relaxing stay, with visually pleasing soft-toned hues, convenient amenities such as a spotless kitchen, and a private pool for a bonus.
The pool area is fenced, so you can enjoy privacy while bonding with your family. Level up the pool party by lighting up the gas grill and preparing some tasty bites to enjoy on the loungers shaded by lush trees.
4. The Palm Villa (from USD 800)
This vacation rental is perfect for travelers who are into resort-like amenities but are not fond of sharing space with other guests. Its main attraction is a breathtaking outdoor pool, nestled in a lush Japanese garden. You can start your mornings with a refreshing soak and end your day with a swim under the starry skies. The 12 ft by 14 ft (3.6 m by 4.2 m) pool is exclusive to guests and comes with stainless steel fountain.
If you’re looking to enjoy a more natural swim, this fully furnished accommodation is within walking distance of local beaches.
5. Well-curated haven for six (from USD 1151)
This bright and cozy accommodation provides vacationers with gorgeous indoor and outdoor living spaces. The interior is a well-curated haven, fashioned with shabby-chic details and equipped with a fully furnished kitchen, a classy dining area, and a comfortable living room.
The main floor leads directly to the private cocktail pool with a sculpture fountain feature. If you book from November through April, you may have the pool heated for an additional fee. An outdoor shower is available, in case you need to wash after a soak.
Top guest reviews
Host:
we met the owner who was so friendly and accomodatingrating details:the property manager was very helpfulrating details:the property manager was very helpfulrating details:the property manager was very helpfulthey were very helpful with checking in and making sure we were ok over our stayRead more reviewsLocation:
location was superb as welleasy access to the free duval loop bus was a plusplenty of room for six adults and the location made for an easy walk to duval streetthe house was in a good location and was as picturedperfect location and very quiet and relaxing after being in main section of town
6. Mango Cottage (from USD 715)
Invite your friends to a much-deserved getaway to Key West, and start the vacation planning by securing this freshly revamped Conch house. While the open kitchen with stainless steel appliances is a sure hit among culinary enthusiasts, the outdoor private pool surely counts as the best feature of the house.
Lush tropical greens accentuate the heated pool. There are sun loungers with a coffee table, where you can take a break from swimming to sip on some fruity cocktails. You can also take advantage of the gas grill and the picnic table for outdoor cookouts.
Top guest reviews
Amenities & Room:
and most importantly beds were comfypool is always good for swimming and all destinations 5-10 mins with bicyclesthe main bedrooms were great with one of the most comfortable mattresses i ever slept onthe pool is amazing 10 out of 10 - would defnitely stay there againCleanliness:
very clean and comfortablecozy clean and beautifully decoratedclean cute and conveniently locatedHost:
regardless we had a great time and appreciate the property owner opening their home to rentersRead more reviewsLocation:
the location was perfect- easy access to everythingplace is cute and really tropicalcute place would definitely stay againprice for rental and location were perfect for our familypros: perfect location with a bike shop grocery and takeout eatery all within a couple blocks
7. Casa Loca (from USD 933)
Make the most of your Key West holiday by booking this three-bedroom property, steps from the top-visited Duval Street. Apart from the convenient location, it also features great amenities. The tourist-friendly and sunny home is fully furnished for vacationers’ convenience. It has WiFi and offers a pet-friendly policy, too. The most sought-after feature is the private swimming pool, easily accessible from the living and dining areas. The heated pool is picture-perfect, accentuated by towering trees, colorful Adirondack chairs, and sunbeds.
Top guest reviews
Amenities & Room:
floor fan did helpthe private pool area is absolutely stunning and serene and hard to leavethe pack and play fit in that room perfectlywe all enjoyed the heated poolthe pool was fantastic after a warm day of biking aroundCleanliness:
this house was not only gorgeous but so clean and spaciousclose to so many different adventures and activities so very clean and comfortable communication was simple and easyperfect location extremely clean comfy beds and the perfect plunge pool we absolutely loved casa locaRead more reviewsLocation:
location is great close to duvalgreat location beautiful housewonderful location and beautiful propertygreat location and beautiful houselocation was great steps away from duval street
Superhost
8. Coconut Cabana (from USD 606)
Thinking of the best way to make your Key West holiday even more memorable? Book this visually pleasing Old Town home that will surely land plenty of snaps on your well-curated Instagram feed.
Besides the aesthetics, previous guests fell in love with the lagoon-like dark-bottomed pool that awaits outside the house. Staying in this Airbnb affords you the opportunity to enjoy instant refreshing soaks without walking all the way to the beach. Plus, the pool is exclusive to you and your vacation buddies. For extra comfort, you can also have it heated!
Top guest reviews
Cleanliness:
the house was super cute and clean and charmingthe property is so charming and clean; well appointed for the maximum of six guestsRead more reviewsLocation:
easy to walk just about anywhere you want to gothis house was great the location is right off of duval street but still nice and quiet at night
9. Secret Villa II (from USD 1275)
This three-bedroom villa is the right pick for you if you’re planning to spend a laid-back vacation in Key West.
In addition to a lovely kitchen with granite countertops, WiFi access, and a parking space, it entices guests with a beautiful outdoor pool area exclusive to them. Lush trees provide the right amount of shade, so you can enjoy soothing dips even on warm mornings. The pool is fenced-in and can be heated for better enjoyment. Sunloungers front the pool, so you can relax poolside and bask in the fresh air.
Top guest reviews
Amenities & Room:
dining table is outside on patio facing the pool only functional if weather is idealCleanliness:
bathrooms were clean updated and well equipped with soaps hair dryers etcexceptionally clean and centrally locatedclean fully loaded with linens towels kitchen supplies and everything was in perfect working orderit's beautifully appointed and spotlessly cleanthe house is extremely clean classy - and full of everything you needHost:
jim was a great host and responded promptly to all of our questionshe's a wonderful host and takes great care to make sure his guests are happyhe was available for any questions (very responsive) and made wonderful restaurant recommendationswe were greeted by a friendly and helpful host who was there to help with anything we neededjim was responsive friendly & a pleasure to deal withRead more reviewsLocation:
perfect house in an amazing locationwonderful place great location near everythingwonderful place and great locationthe location was absolutely perfect so private but so close to everythingfantastic location and house in the heart of key west
10. Brisa Fresca at Truman Annex (from USD 774)
If you are into pretty accommodations and upscale amenities but dislike the hotel and resort setting, then this gorgeous Airbnb with a dreamy outdoor space will surely excite you. From the pastel-colored interiors to the lush garden with bright greens and a swimming pool for a centerpiece, everything about this guesthouse is pleasing to the eyes.
The star of the show is definitely the private pool, which you can admire from the balcony. It is heated, with chaise lounges around it available for relaxing. You can also enjoy an alfresco meal by the pool.
Dive into Key West's sparkling waters
With gorgeous white-sand beaches, endless must-try dining spots, and a vibrant party scene, Key West has all the makings of a fabulous summer destination. Vacationers can level up their stay by choosing the best accommodation on the island; one with a pool is surely going to make it memorable. Use this list of the best Airbnb vacation rentals with private pools in Key West as your guide when you plan a visit.
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