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

An aerial view of a modern villa reveals a sleek structure surrounded by lush greenery. A private in-ground pool is situated on the patio, accompanied by several lounge chairs. The property is enclosed by landscaped gardens, enhancing its serene and inviting environment.

Apartment in Vieques

4.98 out of 5 average rating, 122 reviews

1BR/E - Walk to Beach/Spectacular Ocean View/Pool

"Villa del Sol" is a delightful, modern villa with our 2BR apartment upstairs and two spacious 1BR apartments below. Perched up high with panoramic views of the ocean, it is just a 5-minute walk from two secluded beaches. Fully gated, it has a paved drive and parking, and an in-ground pool. This charming 1BR apartment has high quality furniture and furnishings, a fully equipped kitchen, a large bedroom, flatscreen TV, WIFI & AC. * * * CLICK ON "Show More" BELOW TO CONTINUE THE DESCRIPTION * * *

Superhost

A spacious outdoor area features a private pool surrounded by tropical landscaping. Two lounge chairs in yellow and blue sit beside the pool, while a shaded table and chairs provide a relaxing space. The two-story house stands in the background, with clear skies above.

Villa in Vieques

4.94 out of 5 average rating, 112 reviews

Cacimar House - Pool, Privacy and Sleeps 6

Welcome to Cacimar House - 10 min to South Shore Beaches and 5 min to Isabel Segunda. Cacimar House offers Pool, Privacy, Location, Quality Furnishings, Attentive House Managers. Perfect for Couples, Families and Friends. 3 bedrooms with two Queens and one King for up to 6 people. 3 bathrooms. Air conditioning in bedrooms. Other rooms include: open kitchen, living room , separate dining room, ping pong room, screened in porch and laundry room. Cleaning standards to PR Govt Covid-19 guidelines.

Top guest favorite

An expansive heated saltwater pool is set against a backdrop of turquoise ocean waters and a clear blue sky. Tall palm trees sway gently in the breeze, framing the scene. Lush greenery is visible along the coastline, enhancing the serene environment.

Home in Vieques

4.98 out of 5 average rating, 103 reviews

Surf Side, Private Salt Water Pool, Ocean View

Across from the turquoise waters of the Atlantic Ocean and a short walk to La Chata Beach, you’ll find Surf Side House, with an expansive ocean view, and the main island of Puerto Rico and the sister island of Culebra as your backdrop. Located in Bravos de Boston on Vieques’ North Shore, this peaceful, private single family home features air conditioned bedroom with king size bed, two bathrooms with showers, one outdoor shower and a private heated salt water pool. Maximum occupancy 2 adults.

Superhost

A sunlit outdoor pool area is surrounded by lush greenery. A wooden deck supports a partially covered seating area with modern lounge chairs. Vibrant tropical plants add to the serene atmosphere, while a hammock can be seen, inviting relaxation in this tranquil setting.

Tiny home in Vieques

4.95 out of 5 average rating, 185 reviews

Baez Haus Tiny Treehouse at Finca Victoria

This tiny treehouse is located at the lovely Finca Victoria in Vieques— finca-victoria .com. Set on the magical island of Vieques, this unit gives you all the fun of a treehouse and the unique floor plan of a tiny house! The first floor has a deck surrounded by a garden with a kitchen, bathroom, closet, and outdoor shower. Upstairs you'll find a queen-sized bed, and a beautiful balcony with an amazing ocean view. Complimentary yoga and vegan, Ayurvedic breakfast are included in your stay.

Top guest favorite

A vibrant two-story building is showcased, featuring a Puerto Rican flag prominently displayed. The exterior is painted in refreshing shades of teal and white. Lush greenery surrounds the property, with a stylish overhang and colorful umbrellas visible, emphasizing a welcoming atmosphere for guests.

Apartment in Vieques

4.98 out of 5 average rating, 173 reviews

Esperanza 1 BR Apt, Pool, Walk to Beach & Top Food

- Adults Only (No Kids: 18+ Only) - Pool (Open 7am - 7pm) - AC in Livingroom & Hot Water - 1 Bedroom Apartment with Kitchen - New Queen Bed with AC and TV in room - Beach Towels, Chairs, Snorkel Gear - Same Day Bookings Accepted - No Pets/No Smoking Situated just 1.5 blocks away from pristine beaches and top restaurants. Your choice to take it easy after a long day in the sun or have a night out (all within walking distance). For 20+ years guests have stayed at Coco Loco for a great getaway.

Guest favorite

Home in Vieques

4.93 out of 5 average rating, 119 reviews

Casa Blanca with pool, tropical garden and rooftop

Experience a true authentic Caribbean vacation at our recently renovated home with a pool, rooftop and newly installed gorgeous tropical garden. Enjoy beautiful sunrise from the front of the house, the colorful sky during sunset hours from the rooftop and have a peaceful sleep with a subtle sound of the waves from the Atlantic ocean. Your family will be close to everything when you stay at this centrally-located place whether you are commuting from the airport, ferry terminal or Esperanza.

Guest favorite

A serene outdoor area is depicted, featuring two lounge chairs with orange and red striped cushions beside a small pool. Lush green foliage surrounds the space, offering a tropical ambiance, while a covered bar area with seating provides a shaded spot for relaxation.

Cottage in Vieques

4.99 out of 5 average rating, 106 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!

Superhost

A serene outdoor area features a shared pool surrounded by lush greenery, with views extending to a distant landscape under a partly cloudy sky. Two modern white chairs and a spacious sunbed are positioned near the pool, inviting relaxation and enjoyment of the scenery.

Loft in Vieques

4.85 out of 5 average rating, 208 reviews

Eco Hideaway with Ocean Views and Private Patio

This tropical hideaway, designed by acclaimed architect John Hix, is a tranquil oasis perched atop a breezy hill with breathtaking views of the Atlantic Ocean to the north and the Caribbean to the south. The loft features a private terrace, open-air shower, well-equipped kitchen, high thread count sheets, oversized plush towels, strong WiFi, and a uniquely beautiful shared pool. Despite the privacy of the property, Vieques' best beaches, restaurants, and trail heads are minutes away.

Top guest favorite

A plush outdoor deck features a refreshing plunge pool surrounded by lush greenery and tropical plants. Shade is provided by a large umbrella, while serene sunlight filters through the foliage, creating a tranquil atmosphere for relaxation.

Vacation home in Vieques

4.98 out of 5 average rating, 127 reviews

Casa Borinquen

This homey vacation rental is a brand new construction and is a great place to enjoy the outdoors. The interiors feature a modern design, a full kitchen, full bathroom, outdoor shower, and sleeps 3 people. Listen to the sound of the coquis at night and enjoy the tropical breve e, relaxing in the beautiful plunge pool or grilling on the outdoor deck, surrounded by lush palms, fruit trees (breadfruit, lemons, bananas, plantains, cashews), and herbs (mint, sweet peppers, oregano).

Guest favorite

A well-maintained pool area features a refreshing swimming pool surrounded by lounge chairs. A patio set provides seating, while a barbecue grill is positioned nearby. Vibrant yellow and orange accents contrast with the greenery of the surrounding landscape, creating a welcoming outdoor space.

Apartment in Puerto Ferro

4.78 out of 5 average rating, 305 reviews

SoliMar Guest Studios Azul unit/POOL/Sea View

Welcome to SoliMar Guest Studios We are centrally on island in between Isabel & Esperanza overlooking the Caribbean! SoliMar is less than ¼ mile from the Wildlife Preserve entrance, which is home to Vieques’ best beaches! SoliMar sits on two-acres that are yours to explore. With 7mango trees, horses & iguanas roaming about, relaxing hammock, poolside patio, and a POOL! One of the few that accepts 1 night stays! Different discounts activated when staying 2+ nights!

Guest favorite

A refreshing saltwater pool is surrounded by lush tropical gardens and outdoor seating. The view of the ocean is visible beyond the greenery, and a hammock can be seen, inviting relaxation under the shade of palm trees. A serene outdoor space is created with ample sunlight.

Home in Esperanza

4.92 out of 5 average rating, 126 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.

Guest favorite

The image features a light-filled outdoor space with a private plunge pool that reflects the blue sky. Double doors lead into a bedroom with a comfortable bed visible through the open entry. The surrounding walls provide privacy while allowing natural light to enter.

Cottage in Vieques

4.99 out of 5 average rating, 221 reviews

Casa Corona - Amazing Views, Pool, Close to Beach

Experience this newly renovated home with constant ocean breezes and breathtaking views of the Corona Reef, Culebra and the "Big Island." This cozy cottage offers 'casual luxury' with premium furnishings and cool, comfortable linens and fabrics. Enjoy the ocean-facing plunge pool and outdoor shower. Located just past the former W Resort on a private fenced/gated lot that's minutes from everything (airport, ferry, restaurants, beaches and shopping).