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.

0 of 0 items showing

1 of 3 pages

Guest favorite

Cottage in Vieques

4.99 out of 5 average rating, 173 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, or take a short walk (or drive) to a beautiful beach. Located just past the former W Resort on a private fenced/gated lot that's minutes from everything (airport, ferry, restaurants and shopping).

Sep 9 – 16

G$49,285 GYD per night

Guest favorite

Guest suite in Vieques

4.97 out of 5 average rating, 65 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.

Oct 11 – 18

G$40,529 GYD per night

Guest favorite

Guest suite in Vieques

4.99 out of 5 average rating, 102 reviews

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

"Villa del Sol" is a delightful, modern villa with our 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 * * *

Oct 24 – 31

G$35,609 GYD per night

Guest favorite

Tiny home in Vieques

4.95 out of 5 average rating, 176 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.

Jan 27 – Feb 3

G$81,028 GYD per night

Guest favorite

Home in Vieques

4.98 out of 5 average rating, 84 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.

Jul 21 – 28

G$59,523 GYD per night

Guest favorite

Vacation home in Vieques

4.92 out of 5 average rating, 39 reviews

Ocean front home w/pool for 4 – CASA OCEANA in VQS

Enjoy the best views of the ocean from this perfectly situated 2-bedroom home. Casa Oceana sleeps 4 with a California King, and a convertible Queen (or 2 twins). A full kitchen allows for meals at home, or conveniently located, you can walk to restaurants and stores in a short 10 minutes. All new amenities throughout. Relax by the pool and listen to the sounds of the ocean, or enjoy a yoga session while overlooking the horizon of the Atlantic Ocean and views of the main island of Puerto Rico.

Nov 22 – 29

G$97,268 GYD per night

Guest favorite

Home in Vieques

4.93 out of 5 average rating, 76 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.

Apr 29 – May 6

G$45,975 GYD per night

Guest favorite

Cottage in Vieques

4.99 out of 5 average rating, 82 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!

Apr 21 – 28

G$57,668 GYD per night

Guest favorite

Vacation home in Vieques

4.97 out of 5 average rating, 63 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.

Apr 24 – May 1

G$31,748 GYD per night

Superhost

Loft in Vieques

4.86 out of 5 average rating, 159 reviews

Architectural Loft with Caribbean Views

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.

Oct 23 – 30

G$34,733 GYD per night

Guest favorite

Vacation home in Vieques

4.99 out of 5 average rating, 78 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).

Mar 3 – 10

G$34,839 GYD per night

Superhost

Apartment in Vieques

4.9 out of 5 average rating, 134 reviews

SoliMar Guest Studios Sol~Flora Unit/POOL

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!

Jul 7 – 14

G$25,897 GYD per night