A vibrant tourist hot spot, Key West is an island city with plenty to offer. Enjoy your fill of charming Cuban coffee shops, aromatic bakeries, mouthwatering restaurants, and more. Literary fans will want to check out The Hemingway Home and Museum, while history buffs can head to Truman Little White House. Popular hubs include Old Town, particularly the thriving Duval Street that boasts everything from colorful bars to intriguing art galleries. With the temperate weather, you might want accommodations where you can take an invigorating dip. For options, scroll down for a list of the best Airbnbs with pool in Key West, Florida.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to pool. The image galleries get refreshed with the latest updates regularly. They were last updated on April 12, 2024.
1. Big Blu (from USD 668)
Boasting eye-catching beauty in every direction, this refurbished five-bedroom home is a prize. Big Blu comes with plenty of features, from top-of-the-line appliances to umbrellas if the weather turns stormy. Up to 12 guests are welcome to stay in this luxurious rental.
The lush backyard is an oasis of relaxation, and the heated swimming pool is one of its highlights. Guests can practice their bocce ball skills or sip their favorite drink in the cozy outdoor seating area.
Top guest reviews
Amenities & Room:
the rooms and furnishings gave off a great vibehuge comfortable bed in a studio with lots of natural lightthe room itself was air-conditioned on arrival and decorated very wellthe place is comfortable clean and updated with stylish furniture decoration and amenitiesthe cuban coffee a couple doors down at the laundry mat is deliciousCleanliness:
clean and spacious suitesshawn’s place was great very clean and stylish and the bikes were awesome to get aroundthe bed was comfortable and the apartment was well-appointed and spotlesssuper cozy and clean very nice locationstudio blu was well decorated comfortable and cleanHost:
shawn was a wonderful hosthe was a great hostshawn was an excellent hostshawn was a great host with good recommendations for key westshawn is really helpfulRead more reviewsLocation:
it’s close to everything and the neighborhood is safe and quietthe location was perfect for us for walking or biking to many main attractionsyou can walk or bike to all of the main attractions key west has to offerthe blu suite is an ideal place to stay for any couple staying in key westthe most stunning room in an incredible location in old town
2. Trendy long-term abode on quiet street
If you’re looking for a fabulous monthly stay in Key West, then this is the place. This sylish two-bedroom house is a prized choice in this city’s lodging landscape. The swimming pool is exclusively yours during your stay, and the cool aqua-tinted water offers an invigorating way to refresh after an exhausting day.
The main bedroom has exterior French doors that open onto the beautiful pool deck, and there’s nice seating. Speedy WiFi and on-site parking are added luxuries.
Key West, Florida, United States
1.05 km (0.7 mi) from The Hemingway Home and MuseumSuperhost
Accommodates: 4
Top guest reviews
Amenities & Room:
house is well appointed with a full kitchen washer/dryer central air and the matresses are suuuuper comfortablegreat outdoor patio with lots of seating options bbq and small dipping poolRead more reviewsLocation:
the location is greatbeautiful and spacious house located close to all the hot spots in key west
3. Long-term hideaway with private pool (from USD 210)
Have the opportunity to live like a local at this 28-night-minimum accommodation. This guesthouse for two is near the popular Duval Street and the bustling harbor area. Surrounded by traditional Key West establishments such as Cuban coffee shops and charming markets, this property allows you to explore the neighborhood with ease.
The interior possesses cottage-inspired furnishings for a relaxing stay with your loved one. The outdoor space shines with a private, freeform-design swimming pool nestled in a manicured yard. Note that the pool is shared between 10 am to 5 pm.
Top guest reviews
Amenities & Room:
like new furnishings unit lovely private deep pool in tropical settingthe bed is comfortable and adequately roomy for two adultsthe pool is outstanding warm salt water pool with beautiful patio surroundingwe would highly recommend the pool cottageCleanliness:
it is exceptionally cleanvery nice and clean bathroom and bedroomthis place is beautiful very clean and with everything you need to cook in the kitchenthe cottaage looked brand new clean and very comfortable and roomyHost:
julie the host is wonderfuljulie and tom are friendly and accommodating hostsjulie is more than a super host she is a kind beautiful personand julie and tom are thoughtful and gracious hoststhank you julie for being an awesome host and a great time place to stayRead more reviewsLocation:
but the place is also walking distance from most popular sites)the key west action nicely located close to a lot of events and local fare (restaurants)it's an easy walk to all of the old town attractions bars restaurantsvery lovely stay with the fact it's in a quiet neighborhood just blocks from (duval st
4. Puerta Coralina (from USD 315)
You won’t be able to resist this two-bedroom abode with an attractive exterior. Puerta Coralina is just as appealing inside, with rich wood accents, casual furnishings, and bits of pretty seaside decor. The uniquely-shaped plunge pool with a sparkling waterfall offers a great spot to cool off on a hot afternoon, and guests can even dine poolside on a pleasant evening.
The outdoor space provides a tall wood fence for privacy, and there’s even an outdoor shower for convenient rinses.
Top guest reviews
Amenities & Room:
two beds with private baths was perfect size for my familythe rooftop deck was also great and the pool was the perfect sizegreat house with a small private poolsuper location cozy clean and includes nice amenities including a little oasis and pool in the yardeach bedroom has it's own private bathroom which was great for traveling with friendsCleanliness:
the house was clean and well maintainedclean house with very comfortable set-upclean and very easy check-in processthe house is well appointed very clean and nicely furnishedclean with lots of space and bathroomsHost:
she is amazing energetic kind and very thoughtfulgreat place great host can’t wait to come backRead more reviewsLocation:
great house in a great locationlocation is a number of blocks from downtown but we enjoyed the walk and exercisegreat house within walking distance of bars and restaurantswe also liked the little shop/deli close by to grab things as neededwe literally walked everywhere around the island without any problems
5. Deluxe apartment in bygone-era building
Found in a structure from the 1920s, this upscale one-bedroom apartment is a wonderful vacation home. This remodeled accommodation is awash in ultra-modern splendor, and the host provides bikes so you can explore the neighborhood with ease.
The swimming pool is compact and comes with rounded edges and a maximum depth of 5 feet (1.5 meters). Comfortable outdoor seating surrounds the pool, so you can leisurely while away an afternoon in peace.
Key West, Florida, United States
1.36 km (0.9 mi) from The Hemingway Home and MuseumAccommodates: 4
Top guest reviews
Amenities & Room:
the bed and the couch were comfortable( the pull out couch) and they really loved the showerbikes were a great touch - air conditioner was louder than i was anticipatingalso there is no dishwasher in the beautiful designed kitchenthey were working to resolve an issue with the wifi that left the tv not workingCleanliness:
very clean and pretty$100 cleaning fee really? i bet it takes 20 mins tops to deep clean this tiny placegreat place to stay quick communication clean and easy check inthis place is super cleanvery clean and close to everything great communication as wellHost:
great place and great service milan is a very good hostgreat host the host left us a little gift which is a first for memilan was great with communicating and very accommodatingcommunication with the owner was easycommunication with the owner was immediate and responsiveRead more reviewsLocation:
the location was greatgreat place beautiful location wonderful bathroomthis is a beautiful property located about 1 mile away from duval streetgreat place quiet close to everythingthis place was long on style and location was great
6. Angela’s Cottage
Situated in the center of Old Town, this two-bedroom cottage for four is the quintessential Key West dwelling. A slice of heavenly bliss, this accommodation exudes a relaxed feel throughout.
Surrounded by deep-green plants and lush palm trees, the veranda is a standout feature. It boasts a private heated swimming pool furnished with a built-in waterfall. This gives the space a splendid, spa-like ambiance.
Key West, Florida, United States
780 meters (0.5 ft) from The Hemingway Home and MuseumAccommodates: 4
Top guest reviews
Amenities & Room:
the neighbors were really friendly to us the space was clean the beds/pillows and couch were all comfortablewe absolutely loved the pool and outdoor space - it’s truly an island oasisit is extremely comfortable with a lot of living spaceHost:
she is very friendly and knowledgeable about key westallison was as wonderful and kind host and she was a responsive to our needsi can’t say enough positive about our host allisoni highly recommend this as a wonderful place to stay with a super hostRead more reviewsLocation:
the location was perfect and in walking or biking distance to everywhere we wanted to visit
7. Little Mermaid (from USD 265)
Overflowing with many decorative accents, this three-bedroom clapboard house is a delight. Arranged with great care, this well-maintained lodging offers a simple brilliance that you can’t help but fall in love with. Little Mermaid features numerous double doors in the living room, dining room, and main bedroom, providing easy access to the spacious wood deck and shimmering outdoor swimming pool.
This backyard deck is fully fenced for privacy, and a barbecue grill allows for a nice cookout. Free parking is available on the property.
Top guest reviews
Amenities & Room:
fun private pool and outdoor deck areathe private outdoor space and pool were wonderful for our intimate dinners with guest couplesCleanliness:
the house and pool are very clean and well maintainedHost:
david and lisa are fantastic hostsRead more reviewsLocation:
perfect key west getaway close to everything and still quiet and private
8. Professionally designed cottage with freeform pool (from USD 203)
From the delicate starfish collectibles in the window to the brilliant poolside bougainvillea, this lodging offers a miniature paradise. This spacious four-bedroom house is a custom-designed marvel created by two expert architects. The interior possesses pretty tile floors and contemporary furnishings.
Showcasing a quirky coastal vibe, it features a small, heated swimming pool that is the go-to spot for no-fuss relaxation. There’s also an outdoor shower with hot and cold water for convenient clean-ups after a day on the sandy beach.
Top guest reviews
Host:
the neighbors were nice and friendly the house is beautiful with a pooldefinitely felt like home away from homeRead more reviewsLocation:
the location is also great to walk around town and get to duval stgreat place to stay lots of nice cafes and places to get food near by
9. Private triplex with lots of charm (from USD 224)
Stroll or ride a bike to Duval Street from this lovely two-bedroom home that accommodates up to eight guests and displays a casual, upscale vibe. French doors lead to a snazzy outdoor space. Guests who want to take a swim can do so in the private stone swimming pool. The pool’s underwater lighting provides fun nighttime swims. There’s also a trickling waterfall feature.
The yard is encompassed by a 7-foot (2-meter) fence for assured privacy. An outdoor shower is on hand for quick wash-ups.
Top guest reviews
Amenities & Room:
the grotto pool and patio is our absolute favorite; our private corner of paradisepool was amazing with lights at nightCleanliness:
we loved it and it was spotless and lovelyHost:
heather and justin were awesome hosts and always available when you needed themwould definitely recommend this place and these hostsRead more reviewsLocation:
an oasis in key westwe love this place the location is perfect
10. Casa Victoria
Situated in the center of Old Town, this five-bedroom dwelling is a dazzler, boasting a casual, classic Key West ambiance. Casa Victoria can accommodate as many as 12 guests and offers plenty of room to lounge inside and outside. Handsome French doors open to the breathtaking outdoor space that features a refreshing, private swimming pool. The soothing hot tub comes with a waterfall feature.
The huge covered porch with a nifty barbecue is perfect for dining alfresco or simply chilling while savoring your favorite cocktail.
708 meters (0.5 ft) from The Hemingway Home and MuseumAccommodates: 12
Top guest reviews
Amenities & Room:
having the private pool and huge deck was so terrific for our 7-year oldwe all had plenty of space and enjoyed the guest house pool jacuzzi and grillour group of 10 had plenty of room and enjoyed the pool along with the other amenitiesthe pool is small however there is also a heated jacuzzi with waterfall very relaxingwe enjoyed the back yard pool & jacuzziCleanliness:
house was spotless clean check in was very easythe place was clean well kept and comfortableperfect for a large group and very cleanthe house is spacious clean and has a great key west aestheticgorgeous unique convenient clean stayed at casa victoria for my sisters bachelorette weekend getawayHost:
he was attentive and helpful throughout the tripshel and his team were very attentive and made sure our check in went smoothlythe concierge service was extremely helpful on the planning end of our tripour contact shel was so helpful with anything we wantedour host shel was amazing we would definitely love to stay here againRead more reviewsLocation:
location is perfectamazing house loved the locationlocation in the center of town close to many great restaurants and barsgreat house in great condition great locationwe loved the location it had everything we could possibly need
Indulge in Key West's pools
Whether you’re seeking a cozy abode with an attractive, freeform pool or a roomy house with a lovely plunge pool, Key West is the destination that offers indulgent stays. Opt for one of these Airbnbs mentioned above and add a layer of comfort to your time in Key West.
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