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

4.95 out of 5 average rating, 306 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.

Guest favorite

Townhouse in Key West

4.92 out of 5 average rating, 256 reviews

Sparklng clean, renovated, beautiful, and spacious

Introducing a brand new property hosted by AirBnb Superhost Roy Svenningsen. This home was fully renovated in January 2019. It features all new furnishings, stainless steel appliances, new flooring, marble countertops, and top quality mattresses. I look forward to hosting you in this beautiful family oriented gated community situated across from the Key West Golf Course and only 3 miles from Duval St. The home comes with parking for 2 cars. I am always available to answer any questions. Roy

Guest favorite

Guest suite in Marathon

4.98 out of 5 average rating, 193 reviews

Casa Mariposa: Easy walk to Sombrero Beach

***SUMMER SALE*** Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated by Forbes the #1 Airbnb for couples south of Orlando for 2024 and a top 10 Airbnb in Florida. Step from your private suite to our 50' chilled lap pool surrounded with swaying palm trees and tropical foliage, large coral stone patio, and extensive tropical gardens. Avoid beach parking fees at beautiful Sombrero Beach with a short stroll from your suite at Casa Mariposa!

Superhost

Vacation home in Key West

4.87 out of 5 average rating, 269 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.

Guest favorite

Condo in Key West

4.89 out of 5 average rating, 157 reviews

Spacious Updated Waterfront Condo, 2/2 Pool, Dock

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

Guest favorite

Guesthouse in Key West

4.94 out of 5 average rating, 557 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.

Superhost

Houseboat in Key West

4.87 out of 5 average rating, 218 reviews

Key West Luxury Houseboat at Yacht Club Resort

Beat The Heat! Luxury Houseboat in Private Yacht Club! 15 min from DownTown Key West! Sleeps 6. Brand New Central A/C. 1st level - 2 Queen Bedrooms, 2 Private Ensuite Bathrooms on . 2nd Level - Ocean view Living Room, Full Kitchen, Half Bath. Large, Comfortable Sun Decks for lounging fore and aft on both levels and 40'x15' Rooftop Sun Deck. 15 min from downtown KEY WEST. Located at Stock Island Yacht Club. Panoramic Views from 3rd level sun deck POOL, PRIVATE BEACH, Gym.

Superhost

Villa in Marathon

4.91 out of 5 average rating, 222 reviews

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

Guest favorite

Townhouse in Key West

4.96 out of 5 average rating, 246 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!

Guest favorite

Townhouse in Key West

4.91 out of 5 average rating, 125 reviews

Poolside Cottage #411

Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of Key West. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and boat dock. There's also a new bar & grill, Gumbo's, in the resort. When you want to get out and explore KW, you're only minutes from beaches, the Seaport and world famous Duval Street! Bikes, kayaks, paddle boards and golf carts can be rented locally

Superhost

Rental unit in Key West

4.87 out of 5 average rating, 1,147 reviews

At Mine | Key West 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.

Guest favorite

Rental unit in Key West

4.93 out of 5 average rating, 180 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.*