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Vacation rentals with a pool in Roosevelt Roads

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Roosevelt Roads

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite
Apartment in Vieques
4.98 out of 5 average rating, 132 reviews

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

"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 * * *

Top guest favorite
A wooden terrace is shown with a stool positioned near the railing. The sun rises above a distant landscape, casting warm light over lush green hills and the ocean. An infinity pool is visible nearby, blending beautifully with the scenic surroundings.
Tiny home in Fajardo
4.99 out of 5 average rating, 286 reviews

Magical! Ocean view Cabana w/ Pool Spa on mountain

This memorable place is anything but ordinary. You will get to enjoy this amazing and super private space surrounded by nature and unbelievable views of the ocean and the city. Fully equipped with everything you will need during your stay to include kitchen, full bath with rain shower, A/C, living space with 55" TV, dinning and sleeping areas, terrace with killer views, and of course the pool spa with infinity view! And many more. All of this while enjoying of a complementary bottle of Wine!

Top guest favorite
An outdoor terrace features a wooden deck with a table and chairs, providing ample seating. A cozy swing chair hangs nearby, surrounded by lush greenery and expansive views of the mountainous landscape. Decorative string lights add warmth to the inviting setting.
Shipping container in Gurabo
4.98 out of 5 average rating, 218 reviews

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.

Top guest favorite
A serene outdoor area features a sparkling pool surrounded by lush greenery and tropical plants. A shaded seating area is provided by a large umbrella, along with a cozy hanging chair in the background. The peaceful ambiance is enhanced by bright blue skies.
Guest suite in Luquillo
5 out of 5 average rating, 198 reviews

Casa Encanto - Experience El Yunque Rainforest.

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

Top guest favorite
A contemporary house is positioned atop a hill, surrounded by lush greenery and palm trees. A winding pathway leads to the entrance, while panoramic ocean views extend in the background, highlighting the beauty of the surrounding landscape.
Home in Ceiba
4.98 out of 5 average rating, 121 reviews

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.

Top guest favorite
A tranquil outdoor pool is seen, featuring a sunbathing area with two sleek lounge chairs. The pool's clear water reflects the bright blue sky with fluffy clouds, while tropical plants enhance the scenic mountainous backdrop.
Tiny home in Naguabo
4.99 out of 5 average rating, 160 reviews

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.

Guest favorite
The image captures a tranquil coastal scene featuring a marina filled with boats moored along a dock. Lush green hills rise in the background, with a cluster of buildings nestled atop. The clear blue waters reflect the sky, creating a serene atmosphere.
Condo in Fajardo
4.83 out of 5 average rating, 130 reviews

Oceanfront Relaxation | High-Floor w/ Views & Pool

Wake up to stunning Caribbean sunrises and fall asleep to the gentle sound of ocean waves at this oceanfront escape in Fajardo. Located in a quiet, gated community with a pool and free Wi-Fi, this 1-bedroom condo features a queen bed, sofa bed, full bathroom, and panoramic ocean views. You're just minutes from El Yunque, island ferries, fresh seafood, and local shops. Whether you’re seeking adventure or pure relaxation, your perfect getaway starts here—book now and experience paradise!

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, 135 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
An inviting infinity pool extends toward a breathtaking view of lush green mountains and the Atlantic Ocean. The sky is filled with fluffy white clouds, creating a serene atmosphere. The pool's clear blue water reflects the vibrant landscape, offering a perfect retreat for relaxation.
Cabin in Gurabo
4.87 out of 5 average rating, 356 reviews

The Best View of PR with infinity pool with Heater

Campo Cielo, es el lugar perfecto para desconectarte y estar en completa conexión con la naturaleza. Disfrutarás del más bello amanecer, desde las montañas del Bosque Nacional El Yunque. Te relajarás y recargarás con aire puro y fresco, mientras te deleitas con la mejor vista en la piscina infiniti y en la terraza. La mejor experiencia para disfrutar de la naturaleza y sentirte a un solo paso del cielo, lo encontrarás en nuestro tesoro escondido, Campo Cielo Mountain Retreat.

Top guest favorite
An aerial view captures two contemporary high-rise buildings situated beside a vibrant marina, surrounded by lush greenery and tranquil waters. The Olympic-size swimming pool is visible near the base of the buildings, while the picturesque landscape features a backdrop of hills under a bright blue sky with scattered clouds.
Condo in Fajardo
4.95 out of 5 average rating, 366 reviews

Our slice of paradise

Spacious studio apartment, located on the 22nd floor with stunning views of the East Coast Icacos and Palomino Islands. Unit has cooktop, microwave, and full size refrigerator. Kitchen is also equipped with utensils, crockery and cutlery. The complex has a laundry area on ground floor with washer and dryer for a small fee. It also has a swimming pool, tennis court, basket ball court and 24/7 security. It’s the perfect place to enjoy the breeze and relax.

Top guest favorite
A wooden cabin is set within a lush landscape, featuring open double doors that reveal a cozy seating area. Comfortable benches are positioned on a wooden deck, surrounded by greenery. A pathway made of stepping stones leads towards the entrance, enhancing accessibility.
Place to stay in Río Grande
4.98 out of 5 average rating, 263 reviews

Glamping at Relaxing Atmosphere In Nature

Glamping at Relaxing Atmosphere In Nature (RAIN) provides a serene and private getaway where you can relish the magic of the rainforest, with the calming sounds of rain, birds, and the Coqui's call. Our latest cabin is outfitted with all the comforts to ensure your glamping experience is unforgettable. Comfortably immerse yourself in the forest's flora and fauna. Escape the bustle of modern life and unwind. We embrace and celebrate diversity; all are welcome!

Guest favorite
A refreshing swimming pool features a cascading water feature along a stone wall. Nearby, a shaded dining area is visible under a red umbrella, accompanied by a set of four outdoor chairs and a rectangular table.
Home in Ceiba
4.9 out of 5 average rating, 104 reviews

Casa Génesis

Spend quality time with your family in a relaxing space. The accommodation allows you to enjoy a hot day in a refreshing pool. Its location gives you the opportunity to explore the beauty of the island's east. Near the residence are various attractions and among these you can find the Las Tinajas River, El Hippie River, Seven Seas Spa, Los Machos Beach, Ceiba Ferry Terminal, Puerto del Rey Marina, Las Croabas…

Popular amenities for Roosevelt Roads rentals with a pool

When is the best time to visit Roosevelt Roads?

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Quick stats about vacation rentals with a pool in Roosevelt Roads

  • Total vacation rentals

    Explore 90 vacation rentals in Roosevelt Roads

  • Nightly prices starting at

    Roosevelt Roads vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

  • Verified guest reviews

    Over 4,290 verified reviews to help you choose

  • Family-friendly vacation rentals

    80 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Roosevelt Roads vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Roosevelt Roads rentals

  • 4.9 Average rating

    Roosevelt Roads stays are highly rated by guests—averaging 4.9 out of 5!