Vacation rentals with a pool in Florida

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Florida

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

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Guest favorite

Home in Punta Santiago

4.98 out of 5 average rating, 145 reviews

Lake and Beach Village, Humacao

Casa privada completamente amueblada y equipada para 6 personas, aire acondicionado en toda la casa, marquesina cerrada para 2 autos, piscina,BBQ de gas, TV 50 pulgadas con Netflix, Internet Wifi, Nevera,lavadora, secadora, estufa, microondas, cafetera, utensilios de cocina, ollas, calderos, vasos, platos etc. Ropa de cama y toallas limpias. Muy cerca de la Reserva Natural de Humacao, y cerca de el Malecón de Naguabo, donde encontrarás una excelente oferta gastronómica con excelente vista al mar

Superhost

Home in Vieques

4.85 out of 5 average rating, 27 reviews

Villa Dos Palmas - Pool Villa - 2 Bedroom Oceanfro

Villa Dos Palmas - Pool Villa sits so close to the beachfront the waves are lapping at your feet. The Pool Villa accommodates your group of up to 6 people with the perfect place to enjoy your very own private infinity pool. One additional amenity is that it is the only vacation rental on Vieques with moorings for your boat. Located very near the town of Isabel Segunda the home is within easy walking distance to restaurants, pubs, the bank and ATM, groceries, and shopping galleries. PROPERTY

Guest favorite

Guest suite in Vieques

4.95 out of 5 average rating, 83 reviews

Serene 2 bdrm. Pool w view + perfect for families.

Private, spacious and light-filled 2 bdrm apartment w/ 10-foot ceilings on top of a quiet hill. 3min. from beach and 5 min. from the main town of Isabel Segunda. This property was designed for the view! Every day you will have one of the best views of the island, ocean, Culebra, and the famous Vieques sunset. Enjoy the view from your apartment, your private deck, or your private pool. Outdoor shower, pool and beach gear included. Lg bdrms with comfortable queen beds. Full kitchen+bbq grill.

Guest favorite

Home in Vieques

4.99 out of 5 average rating, 100 reviews

Casa Tesoro-pool home. Walk to beaches/restaurants

Newly renovated home with constant ocean breezes and breathtaking views of the Caribbean Sea and Esperanza Keys. This home offers 'casual luxury' with premium furnishings and cool, comfortable linens and fabrics. We are located in the heart of Esperanza, no car is needed as we are less than a 5 minute walk to the Malecon, Restaurants and 2 minutes to the neighborhood Grocery store. Coco, Esperanza and Sun Bay beaches are a short walk away or enjoy your private pool, one of a few in Esperanza.

Guest favorite

Cottage in Vieques

4.99 out of 5 average rating, 95 reviews

Private Pool Bar with Panoramic View! 5* A/C, WiFi

Designed as a private paradise for two adults only, Bonita Vista is centrally located and easy to get to, yet very private. This new hillside retreat features a large covered pool bar with breathtaking views overlooking the Vieques National Wildlife Refuge and the Caribbean Sea. Artifacts from the sugar cane era offer connection to Vieques history. An afternoon poolside slips easily into sunset cocktail hour and dinner from the grill, a swim under the stars or magical moonrise over the bay!

Guest favorite

Home in Ceiba

4.91 out of 5 average rating, 117 reviews

Coastal Getaway with Pool, Game Room & Ocean View

This self-sufficient home offers a tranquil residential vibe alongside quick access to most important places in the East Side. We know how important it is to feel comfortable and relaxed when you arrive back from a long day of sightseeing. This idea is what inspired us to provide everyone that stays a place to recharge, relax and enjoy. Our experiences include: personal chef, decorations for any special occasion and picnic dates. Private boat by referral can also be arranged.

Guest favorite

Home in Vieques

4.95 out of 5 average rating, 116 reviews

Location, Location, Location with Pool

House, 3 Bedroom, 2 full Bathrooms, Sleeps 6 Casa Angie is a newly renovated home across the street from the ocean and a 3-minute walk to the Malecon in the fishing village of Esperanza. The Malecon is a boardwalk fronting the ocean with restaurants, bars and boutique shops, along with water sports rentals. Our Casa with its brand new kitchen is completely equipped for your convenience; whither dining in or barbecuing by the pool, you will surely enjoy your island experience.

Guest favorite

Home in Punta Santiago

4.94 out of 5 average rating, 137 reviews

We are back! Puerto Rican paradise awaits you!

Please ask about our other home nearby. Beachfront living with pool - 4 bedrooms. Lose yourself in paradise in this newly remodeled beachfront home with pool - 4 bedrooms, 3 baths. You will have the best of both worlds - beach and pool - for your pleasure. Enjoy unobstructed ocean/beach views from bed and through the house. Perfect for family vacations, romantic getaways or just to get away from it all. Cribs and high chairs available for little vacationers.

Superhost

Home in Esperanza

4.91 out of 5 average rating, 105 reviews

Casa Amor Home Esperanza Salt Pool- close to Beach

Casa Amor in Esperanza hills is a dream escape. A case of privacy, offering two fully separate suites, an outdoor dinning area with views of the of the ocean, saltwater pool, and BBQ. Breezes are free! A lovely outdoor shower for a rinse under the stars, a hammock for lazy afternoons… From the pool and gardens, you’ll find ocean views. (Clothing optional) It’s private and peaceful! Tucked into a safe locals’ neighborhood, three blocks from the nearest beach.

Superhost

Home in Punta Santiago, Humacao, Puerto Rico

4.87 out of 5 average rating, 63 reviews

Lakeside Casita w/ pool+Grill+1 min. to beach

A lake side tropical paradise walking distance from the beach with its own private pool. Perfect for family gatherings and vacations and romantic getaways. Just minutes from nature reserves and many other attractions; this little piece of paradise helps guests immerse themselves into the nature and culture of Puerto Rico being located in a quiet beautiful community. Suitable for children, pets, and up to 11 people!! 15 minute from ferry to culebra.

Guest favorite

Home in Vieques

5 out of 5 average rating, 11 reviews

New on market-Cool Vibe Island Home with a pool!

Kick back and relax in this calm, stylish space. Everything you need for a tranquil, peaceful vacation. *brand new pool! Up and over the hill and you will find yourself at the some of the most beautiful beaches on the Carribean side. Conveniently located off Hwy 200 with access to the super Mercado, gas station, food trucks as well as local restaurants.

Guest favorite

Condo in Fajardo

4.93 out of 5 average rating, 87 reviews

Casa Family 3 bedroom condo with pool & gated area

Five minutes from Fajardo marina where you will find the best snorkeling trips. Very close to Seven seas beach. The ferry to the islands (Vieques, Culebra) are just a short drive away. Supermarket at the beginning of the complex. 15 minute drive to Luquillo beach and the magical, spectacular rainforest (El Yunque) What more can you ask for? Book today!