
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.

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. Excellent wi-fi, satellite TV and stereo equipment.
4.95 out of 5 average rating, 129 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.
4.99 out of 5 average rating, 164 reviews
Esperanza 2 BR Apt, Pool, Walk to Beach & Top Eats
✔ Adults Only (All 18+) ✔ 2 Queen Beds ✔ 3 Cold A/Cs ✔ 3 Smart TVs ✔ Hot Water ✔ Beach Chairs, Towels & Snorkel Gear ✔ Pool & Tropical Yard ✔ Private 2 Bed Apt (#2) For over 20 years guests have stayed at Coco Loco in Vieques for the perfect Caribbean vacation home. Our guests love to see the Bio Bay, have beach days, explore the island, and be on island time. We are just 1.5 blocks from the beach, El Malecón (Boardwalk) with top restaurants, live music, and everything Vieques has to offer.
4.97 out of 5 average rating, 427 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.
4.93 out of 5 average rating, 149 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!
4.98 out of 5 average rating, 126 reviews
Casa Borinquen
The perfect place to unwind and enjoy the outdoors. Designed with a modern touch, it features a fully equipped kitchen, full bathroom, outdoor shower, and accommodates up to 3 guests. Relax in the beautiful plunge pool, enjoy a barbecue on the terrace, and fall asleep to the soothing sounds of the coquí frogs, surrounded by lush tropical greenery. Sweet and friendly little cats may occasionally stroll through the outdoor areas, adding to the natural charm and warm ambiance of the property.
4.97 out of 5 average rating, 182 reviews
Vieques ocean view eco villa+pool
-Privately nestled on three acres with Caribbean Sea views from the second floor. -Three private bedroom suites - mosquito nets. Villa doesn’t have Ac -Spa and yoga classes nearby at Finca Victoria -Full service amenities can be arranged: stocking the fridge, chef, massages. -Gunite swimming pool - solar powered -Each bedroom has its own bathroom, dressing area & outdoor shower -The beds are fitted with quality 400-count cotton linens - Strict no children under the age of 10years policy
4.96 out of 5 average rating, 103 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.
4.85 out of 5 average rating, 258 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.
4.94 out of 5 average rating, 158 reviews
Home for 9 with Pool and Solar Panels in Vieques!
Spectacular modern and stylish home in Vieques Island! This spacious home will provide the perfect retreat for you and your group. The house consist of 3 bedrooms and 2 baths, a fully stocked kitchen and a new and stylish outdoor patio with pool. Your Vacation are secured with us as we have a Solar Energy System and a water cistern. The home can host up to 9 guest, including children. You will be minutes from Restaurants, National Parks and Reserves, and beaches to enjoy.
4.9 out of 5 average rating, 164 reviews
Beachfront Villa surrounded by Ocean w/pool
Unbeatable views and location: There is no property like the historic "Las Piedras" in all of Vieques. Situated into green rock jutting into the ocean it has spectacular views of coral reefs below and Caribbean Islands from decks pool and BR's. Our private, gated property has its own entrance to La Chata beach. Swim and snorkel from your "front yard" or explore morning tide pools. The villa offers ample space for entertaining indoors and out, and comfort for up 8 guests.
4.98 out of 5 average rating, 104 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.
4.89 out of 5 average rating, 152 reviewsPopular amenities for Florida rentals with a pool
House rentals with a pool

Surf Side, Private Salt Water Pool, Ocean View
4.96 out of 5 average rating, 120 reviews
5Br -3Bth Infinity Pool & Ocean view &Walktobeach
4.78 out of 5 average rating, 107 reviews
Casa Mami y Papi including private suite
4.95 out of 5 average rating, 103 reviews
El Saco Country House
4.91 out of 5 average rating, 111 reviews
Casa Escape Close to the ferry (Vieques and Culebra)
4.93 out of 5 average rating, 128 reviews
Casa Corona 2026 - Central location with a pool
5.0 out of 5 average rating, 19 reviews
El Secreto -Secret Ocean Front Oasis
5.0 out of 5 average rating, 26 reviews
Martineau Beach Haven
4.87 out of 5 average rating, 31 reviewsOther holiday rentals with a pool

Oreanda – Casa Limon
4.94 out of 5 average rating, 160 reviews
Serene 2 bdrm. Pool w view + perfect for families.
4.95 out of 5 average rating, 136 reviews
Cielo Studio tranquility w/pool in rural location
4.98 out of 5 average rating, 125 reviews
Vieques Villa Gallega - Oceanview w/Infinity Pool
4.91 out of 5 average rating, 67 reviews
Private Retreat w/ Pool, Stunning Views & Wildlife
5.0 out of 5 average rating, 21 reviews
Vieques Garden House - Oasis: Relax w/ SUV & Pool
5.0 out of 5 average rating, 91 reviews
Vieques Boutique Beach House
4.94 out of 5 average rating, 35 reviews
Caribbean Oasis: 5BR Villa with Stunning Views
4.9 out of 5 average rating, 69 reviewsDestinations to explore
- San Juan Holiday rentals
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- Las Terrenas Holiday rentals
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- Fajardo Holiday rentals
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- Plaza Las Americas
- Punta Bandera Luquillo PR
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- Isla Verde Beach West
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