
Holiday rentals with a pool in Puerto Rico
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Top-rated rentals with a pool in Puerto Rico
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Monte Lindo Chalet (Romantic cabin in the woods)
THE ENTIRE PROPERTY FOR TWO GUESTS, EXCEPT THE TWO SECONDARY ROOMS THAT WILL REMAIN CLOSED When you arrive at Monte Lindo Chalet, the first thing you experience is a feeling of deep peace. When you close the gate of the estate you realize the security and privacy of the place. In front of the Chalet you can appreciate a beautiful structure surrounded by lush nature that invites you to be creative. Live the experience you've always dreamed of with your partner and create memories for a lifetime.

Private Pool and Entertainment Area at Lunabelapr
Plan a relaxing getaway while enjoying a private pool with sundeck, fire pit, 100-inch screen projector, gazebo, and pool table that are exclusive for the guests of Lunabela. This special place is just a 10-minute drive from both the beach and Guajataca River, and within walking distance to the mall, restaurants, and bakeries, making it easy to plan your visit and explore Isabela. The unit has a fully stocked kitchen, AC, king-size bed, Wi-Fi, TV, free parking space, BBQ grill, and board games.

Casa Lola PR
In Casa Lola, nature is the protagonist of a hidden spot surrounded by mountains in Isabela. Unique views and a perfect place to disconnect and reconnect with your couple…. Come and enjoy our beautiful cabin on top of the mountain, completely private and experience the best nature environment. Fully equipped kitchen, indoor and outdoor showers, loft room with amazing sunrise and sunset views, infinity pool, sun chairs and relaxing hammock. A place that invites you to come again…..just enjoy.

Sol y Luna Mountain Retreat Hacienda
Enjoy the lovely setting of this romantic spot in nature and discover the serenity in our cozy farmhouse. This private villa wraps you in a lovely and peaceful environment with majestic mountains all around. The house is fully equipped for your convenience. It is ideal for couples in need of a nice getaway or just reconnect with yourself and nature. It is on a gorgeous tropical private 3 acre estate with private pool. Located in Villalba, Puerto Rico, just 50 minutes from Ponce's Airport.

Vista Linda Haus
At Vista Linda Haus, from the moment you start the journey to the beautiful town of Gurabo, the adventure begins. A unique experience towards the favorite destination. You will find panoramic landscapes, lakes, mountains, farms, cities, and a community with the Puerto Rican warmth of our mountains. Just 35 minutes from the Luis Muñoz Marín International Airport, over 1,000 feet above sea level, you will breathe freedom and peace, in a harmonious environment full of energy and pure nature.

Casa Encanto Rainforest Retreat
This Guest Suite, on the lower level of our exclusive luxury villa, Casa Encanto, is the perfect tropical getaway. Nestled in the peaceful and lush foothills of the El Yunque Rain Forest, Located in Luquillo with many nearby attractions. You’ll have easy access to downtown Luquillo, El Yunque National Rainforest, Luquillo Beach, Caribali Adventure Park, Las Paylas, charter boat trips, snorkeling, zip lines and much more. The Guest Suite is fully solar with Tesla Batteries and backup water

La Casita: Private Heated Pool W/ Ocean Views
Nestled atop a lush hill at the beachfront town of Ceiba, this 2-bedroom house is a haven of luxury & tranquility, offering a spectacular panoramic view of the ocean, the rainforest, mountains & neighboring islands. As you approach the property, a winding driveway bordered by vibrant, blooming flowers leads you to the entrance, setting the tone for the enchanting retreat that awaits. Just a 1-hour drive from SJU's International Airport & half hour ride from El Yunque National Rainforest.

Casa Suiza (Mountainous Area)
Casa Suiza es un lugar para escapadas románticas, sólo para parejas. Estamos ubicados en lo alto de la montaña, es muy privado y alejado de la ciudad, a una hora de distancia de San Juan y el Aeropuerto Internacional de Puerto Rico. Tenga en cuenta que dirigirse a nuestra propiedad es por calles con curvas y algunas pendientes empinadas, pero completamente transitables. Recomendamos rentar un vehículo SUV o un 4x4 para su tranquilidad, si no está acostumbrado a transitar en la Montaña.

La Casita de Lele
La Casita de Lele offers a space to disconnect from the hustle and bustle of the city, where you can live a country experience. You will find a cozy and unique atmosphere with a panoramic view to enjoy the nature and tranquility that is experienced in the mountains of the island. La Casita de Lele is minutes away from shops and exploration areas. In addition, it is located near the Gastronomic Route of the 149 of PR. Come, Disconnect, Breathe and Live. Dare to live as Lele lived.

Chalet De Los Vientos (Chalet of the Winds)
Chalet de Los Vientos is a beautiful and cozy tiny house located in 25 acres , in the mountains of Caguas , PR at 2000ft above sea level with a spectacular view, heated pool and the privacy you deserve! This Chalet is a couples retreat and the perfect getaway for you and your loved one to disconnect from the daily routine. If you love coffee as much as we do, there is a dedicated coffee bar for you to make your espresso drink. We also have a 19Kw Caterpillar backup generator 💡

Escape Puerto Rico | Luxury Dome + Pool + Views
Escape to a romantic and luxurious glamping dome surrounded by the lush mountains of Cayey, Puerto Rico🌿. Enjoy total privacy with a private heated pool, panoramic views, and elegant design — the perfect retreat for couples or solo travelers seeking peace, comfort, and connection with nature. Wake up to mountain sunrises, relax under the stars, and experience a serene escape just an hour from San Juan — were nature and luxury meet in perfect harmony.

Best location with pool, steps from beach!
Wake up in a luxurious king bed with premium bedding, gazing out at your private pool framed by lush palm trees. Start the day with breakfast from the fully equipped kitchen, then catch up online with blazing-fast Wi-Fi under the shaded pergola. Cool off in the pool or rinse in the outdoor hot shower before walking just 50 yards to San Juan’s best beach. Ideal for couples, solo travelers, remote workers, or small families seeking comfort and style.
Popular amenities for Puerto Rico rentals with a pool
House rentals with a pool

Villa Despacito, Modern, Ocean View w/Private Pool

Mountain Retreat • Private Pool • Nature + Peace

Suite with Private Pool

Oceanfront 4BR w/ Private Pool + Beach Access

Romantic Casa Diaz | Private Pool + Ocean Views

Monte Niebla, a piece of heaven in the mountains

Serena Cabin: Saltwater Pool-King Bed-In Puntas

Private pool and breakfast in D'la isla suite
Condo rentals with a pool

Casa Dani Spectacular|Modern|New 2 bed|2 bath

Deja Blue BeachFront Apartment @ Isla Verde (Green Island)

Isla Verde Beachfront Studio near restaurants,bars

Beautiful Beachfront Condo in Isla Verde/San Juan

Caribbean Beachfront King bed with large balcony

Palms & Ocean View 1br 1bth + Pool + Beach Access

Breathtaking Ocean View Apartment

Beachfront & Pool at the Best Location in Condado
Other holiday rentals with a pool

Private Beach House/Private Pool/Heated

Design Suite「 POOL」Walk to Beach | DUNA by DW

HORNED DORSET- PRIVATE PLUNGE POOL

Glamping at Relaxing Atmosphere In Nature

The Best View of PR with infinity pool with Heater

Bonita Mar Chiquita Beach House Couple's Retreat

Blackandwoodcabin Cabin/ chalet in Aguadilla

Idyllic Beachfront Penthouse w/Private Plunge Pool
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