Vacation rentals with a pool in Key West

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Key West

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Key West

4.94 out of 5 average rating, 271 reviews

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

Apr 21 – 28

ﺩ.ﺇ2,052 per night

Guest favorite

Condo in Key West

4.83 out of 5 average rating, 243 reviews

La Dolce Vita, Old Town Steps to Duval! 3 blks bch

La Dolce Vita is a one bedroom, one bath condo with granite galley kitchen, living room, newer a/c, flooring, located in the heart of the Historic District in Old Town and is walking distance to all the shops, restaurants, bars and just steps to Duval Street! You will not need a car with this location. Large wraparound balcony with sitting chairs & table. Extra cleanings for an extra charge Southernmost Beach is just 3 short blocks away. Southernmost Point, Hemingway House, Butterfly World.

Aug 20 – 27

ﺩ.ﺇ975 per night

Guest favorite

Guest suite in Marathon

4.98 out of 5 average rating, 184 reviews

Casa Mariposa: Easy walk to Sombrero Beach

Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, 1 0f 24 amazing AirBNB rentals in the Keys, and, in 2023, 1 of 23 Amazing Airbnbs In Florida Keys. Step out from your private suite to our 50' lap pool surrounded with tropical foliage, large patio, and tropical gardens. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in other lengths of stay.

May 5 – 12

ﺩ.ﺇ798 per night

Guest favorite

Townhouse in Key West

4.87 out of 5 average rating, 174 reviews

*Sparkling new kitchen* 3 bedroom/3 bath home.

Coral Hammock was built in 2004. This home is a spacious 3 bedroom, 3 bath home in a beautifully landscaped gated community. It features 1 king size beds and two queen beds. The kitchen is fully equipped with modern appliances, dishes and cooking utensils. There is a new Whirlpool Duet washer/dryer installed. The salt water pool is perfect for lazing away your days. There is on street parking for two cars. The center of town is ten minutes away. An entire home for the price of one hotel room.

Sep 26 – Oct 3

ﺩ.ﺇ1,721 per night

Guest favorite

Apartment in Key Largo

4.94 out of 5 average rating, 247 reviews

Waterfront Studio 1| Kayaks | Pool |Bay View |Wifi

Escape to Northern Key Largo for a relaxing vacation! Discover great restaurants, beautiful state parks, and marine life. This bright, modern studio boasts excellent views of Manatee Bay, free kayaks and paddle boards, and a full kitchen. With access to a swimming pool and docks, there’s always something to do. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park 22 Min Drive to African Queen Canal Cruise Experience Key Largo With Us & Learn More Below!

Oct 28 – Nov 4

ﺩ.ﺇ651 per night

Superhost

Vacation home in Key West

4.87 out of 5 average rating, 230 reviews

Historic Cigar House. 3rd floor Suite W/Kitchen

This unit is located in the historic "Cigar House" of the Island City House Hotel. Unit 12 is on the 3rd floor and is one of the most requested units in the entire hotel. Your private balcony overlooks the pool. Only 3 blocks from Duval street so close everything, yet quiet enough for a good nights sleep. You will have your own private entrance and use of all the hotel amenities. The space is a private 1BR with a kitchen and NEW sleeper sofa (12/23). In Old Town, walk to everything.

Nov 8 – 15

ﺩ.ﺇ1,687 per night

Guest favorite

Guesthouse in Key West

4.93 out of 5 average rating, 527 reviews

Old Town - Room Opens to Pool and Garden

Located in the heart of Old Town, we are three blocks from Duval Street, a 10-minute walk to Higgs Beach, and around the corner from the best, least-expensive meal in town--El Siboney Cuban Restaurant. We suggest bicycling around Key West. Rentals from We-Cycle Bike Shop can be delivered to our door. Two blocks away, The Duval Loop offers free air-conditioned bus service 7 a.m. until midnight. We also offer a link with recommendations for excursions, tours, & restaurants.

Jun 8 – 15

ﺩ.ﺇ1,240 per night

Guest favorite

Condo in Key West

4.88 out of 5 average rating, 147 reviews

Large waterfront 2/2 end unit with boat slip

Time to fish & relax! Bring your family & friends to this 1350 sqft waterfront corner condo home. Boat slip available on-site with commercial ice machine and fish cleaning station. Located in historic Downtown Key West. Walk/Bike everywhere less 1mi to Duval Street, Seaport, Hemingway House, etc. On-site amenities: heated pool, tiki bar & grills, bike rentals, parking, secure keyless entry, & private elevator. Large park adjacent with tennis courts. 10min from airport (EYW).

Feb 20 – 27

ﺩ.ﺇ2,615 per night

Guest favorite

Condo in Key Colony Beach

4.91 out of 5 average rating, 197 reviews

Oceanfront Breeze, Stunning Views, Beach/Pool

Newly renovated ocean front condo with gorgeous, unobstructed views from every window. Beautiful studio condo on the 1st floor only steps away from the private beach and heated pool. Condo features a fresh, clean interior with brand furnishings, bathroom and kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

Jul 28 – Aug 4

ﺩ.ﺇ1,254 per night

Guest favorite

Townhouse in Key West

4.96 out of 5 average rating, 227 reviews

Stunning Townhouse * Full kitchen! * Sleeps 6

This property is a rare find! Sleeping 6 and located over 2 floors, its located in the beautiful resort of Santa Maria. The condo itself is overlooking the pool, enjoys 2 stunning balconies with its own outdoor furniture. Fully equipped kitchen, 21/2 bathrooms, TVs and wifi throughout. The property is located in one of the best destinations within the historic old town. Just 2 blocks from Duval Street, and also just 2 blocks from the beach. You really can have it all!

Apr 16 – 23

ﺩ.ﺇ2,594 per night

Guest favorite

Apartment in Key West

4.92 out of 5 average rating, 1034 reviews

At Mine | Lovely Suite steps from Duval Street

Beautifully renovated boutique hotel suite steps from Duval Street. This property is situated on a quiet street and offers a private pool and peaceful accommodation for vacationers and business travelers. The unit features a comfortable Queen-sized bed, Mini Fridge, a microwave, Iron and iron board, hangers, TV, and AC. Indulge in Key West's warm weather year-round. This special place is close to everything, making it easy to plan your visit.

Sep 18 – 25

ﺩ.ﺇ1,053 per night

Superhost

Apartment in Key West

4.92 out of 5 average rating, 165 reviews

Duval St Apartment w/ Balcony w/parking Adult Only

This large apartment overlooks Duval Street from a private balcony. Perfect location in the heart of Old Town within easy walking distance of restaurants, live music, and historic sites. Guests enjoy daily complimentary continental breakfast in the garden and dips in our heated pool. *Please note you must be 21 or older to make a reservation on this property and all guests must be at least 18 years old.*

Jul 27 – Aug 3

ﺩ.ﺇ1,674 per night