Holiday 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 favourite

Guest suite in Vieques

4.95 out of 5 average rating, 80 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 favourite

Cottage in Vieques

4.99 out of 5 average rating, 91 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 favourite

Condo in Machos

4.84 out of 5 average rating, 56 reviews

Lovely Caribbean Oasis Condo with pool/gym

Your family will enjoy a blissful stay at a tropical paradise. 3 room 2 bathroom apartment with a balcony. Centrally-located near beautiful beaches, delightful restaurants and espectacular views. 5 min. away from the largest Marina in the Caribbean: Safe Harbor Puerto Del Rey. Where you can take catamarans excursions and explore our beautiful Caribbean sea. Also 12 min. away from the ferry you can take to visit Vieques or Culebra. You are just a click away to enjoy the getaway you deserve.

Guest favourite

Holiday home in Vieques

4.98 out of 5 average rating, 83 reviews

Cielo Studio tranquility w/pool in rural location

The space is quiet and tucked away in the breezy hillside of Monte Carmelo. Rest your eyes on the views of the Caribbean, and rest your feet in the plunge pool. The plunge pool has powerful jets for ultimate relaxation. Wifi throughout the property can also make the sofa swing, deck and pool areas productive as well. Monte Carmelo is a barrio that requires you to have your own transportation, yet is centrally located between downtown Isabel and the ocean front restaurant row of Esperanza.

Guest favourite

Home in Ceiba

4.9 out of 5 average rating, 112 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 favourite

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 favourite

Home in Vieques

5 out of 5 average rating, 38 reviews

Casa Cumbre - Spectacular views, location and pool

This property is on a separate island of Vieques, not main island Puerto Rico. Casa Cumbre is a fully equipped home located in the hills of Los Chivos with unparalleled views of both the Caribbean Sea, bays, and the Atlantic Ocean. The property has a swimming pool, 3 bedrooms, 3 bathrooms (2 en suite), sleeping 6 persons total. Air conditioning is available in all bedrooms although the house captures the breezes. Convenient center island location.

Guest favourite

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 favourite

Guesthouse in Vieques

4.97 out of 5 average rating, 141 reviews

Vieques casita with pool walk to ferry

For adults only intown lovely One bedroom casita walking distance to everything, bank,post office, stores and restaurants, walk to the ferry boat . two blocks from sea glass beach. Your own pool .this is a strict non smoking Located in the middle of lovely town of Isabelle in a compound of rentals sorry no children allowed , cats live outside on property

Guest favourite

Condo in Fajardo

4.93 out of 5 average rating, 86 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!

Guest favourite

Condo in Húcares

5 out of 5 average rating, 14 reviews

Casa Paraiso Beach & Pool Condo Naguabo-Hucares

Bring the whole family to this spacious place with lots of room for fun. 24hr gated access. Beautiful pool, access to private beach, playground for kids, tennis court and basketball court. Close driving distance to Ceiba to take the ferry for Vieques and Culebra, the Luquillo Kiosks and El Yunque.

Guest favourite

Villa in Vieques

4.94 out of 5 average rating, 36 reviews

Vieques Villa Gallega - Oceanview w/Infinity Pool

Villa Gallega is a unique vacation rental villa nested on a gated and private hill. The Villa offers picturesque direct ocean and park views, an immense all natural stone infinity pool, and multiple private terraces. 3 floors, 4 bedrooms, 3.5 bathrooms. The entire Villa and Pool is yours to enjoy.