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Holiday 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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Guest favourite
Flat in Vieques
4.98 out of 5 average rating, 130 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 * * *

Guest favourite
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
4.98 out of 5 average rating, 308 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!

Guest favourite
A private swimming pool is nestled against a backdrop of the ocean and marina, providing panoramic views. Four people are seated at the pool's edge, enjoying the refreshing water. Lush palm trees sway gently in the breeze, enhancing the tranquil setting.
Flat in FajardUrb. Las Gaviotas
4.93 out of 5 average rating, 145 reviews

Vistamar- Stunning Caribbean views & private pool!

Open, spacious and breezy with full length balcony overlooking Puerto del Rey marina and the islands. Relax, swim in our private pool and take in the beautiful Caribbean views. Short drive to east coast beaches, El Yunque Rain Forest, discounts on boat trips to Icacos and Culebra. Located in a quiet gated neighborhood, the entire 2nd floor of a private home, with private entrances, and easy parking. Full kitchen, BBQ, and washer/dryer make for a comfortable stay. Longterm rental available.

Superhost
A serene pool area is framed by tropical palm trees, with a gazebo featuring string lights in the foreground. The pool reflects the evening sky, while lush greenery surrounds the space, providing a sense of tranquility and natural beauty.
Flat in Ceiba
4.84 out of 5 average rating, 179 reviews

Mountainside Ocean View Pool/Family Fun Ferry

Experience Puerto Rico's rainforest at our mountaintop apartment. Coqui's and owls create a natural background at night. 1 full apartment including garage parking. Full kitchen, full bedroom, living room converts to a queen bed. 18' pool with ocean view 12' gazebo. 3 acres of trails to hike, trampoline, and zip line for children. kayak and beach equipment. transportation to ferry available. Our boat is also available seek a water adventure. very kid friendly - must be ok with dogs.

Guest favourite
The image captures a panoramic view from the private rooftop, showcasing lush greenery and the tranquil blue ocean. Islands are visible in the distance, with a mix of residential buildings lining the foreground, contributing to the serene coastal landscape.
Apartment in Machos
4.9 out of 5 average rating, 206 reviews

Oceanview Bay View Penthouse Beach/Marina/Ferry

Enjoy your island escape at Vista Bahía Penthouse in Costa Esmeralda, Ceiba. Relax away from the hustle while staying just 3–5 minutes from the marina, beaches, restaurants, and shopping. The condo features 3 air-conditioned bedrooms and a fully equipped kitchen. Wake up to beautiful sunrises and unwind on the private rooftop with panoramic ocean views. At night, guests love watching the incredible star-filled sky. Perfect for relaxing, stargazing, and enjoying the peaceful island breeze.

Top guest favourite
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, 210 reviews

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

Top guest favourite
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, 132 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 favourite
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, 170 reviews

Casa Suiza-Private Couple Escape with Heated Pool

Casa Suiza es un retiro de escapadas románticas, sólo para parejas con Piscina Climatizada. Estamos ubicados en la montaña, es muy privado, alejado de la ciudad, a una hora de distancia de San Juan y el Aeropuerto Internacional de Puerto Rico. Recomendamos rentar un vehículo SUV o 4x4 para su tranquilidad, si no está acostumbrado a transitar en la Montaña. Una vez comienzas a subir a la montaña, es por calles con curvas y algunas pendientes empinadas, pero completamente transitables.

Guest favourite
Apartment in Fajardo
4.94 out of 5 average rating, 109 reviews

Villa @ Marina; Near Beach/Easy Access to Islands

You'll love our Villa in Fajardo, Puerto Rico. Minutes away from El Yunque Rain Forest, Fajardo and Luquillo Beaches, top restaurants and most importantly, with easy access to Palomino Island, Icacos Island and the world-famous Flamenco Beach located in Culebra Island. The Villa is located in a gated, clean, safe and quiet community, great for couples and families. Villa Marina has great amenities as well! ***Solar panels, Tesla Powerwall Battery, and Water Tank installed***

Top guest favourite
Tiny home in Luquillo
4.95 out of 5 average rating, 102 reviews

Private Rainforest Retreat ~10 min to Playa Azul~

Visiting El Yunque & Bio Bay? 🌺 Koko Kai Cabana is the perfect retreat - right between Luquillo and Fajardo - for exploring the Best of the East Coast 🇵🇷... You'll enjoy quiet, country life in the mountains of Juan Martin. But just 15 mins to Luquillo Beach, 20 to El Yunque or Bio Bay & shopping in Fajardo is only 7 mins down the mountain. We live on site, but the cabana is on the "3rd level" above the pool. It's private and tranquil... and everything is just for you two!

Guest favourite
Home in Humacao
4.92 out of 5 average rating, 297 reviews

Beautiful House, 24/7 Security, Gated Community

Sanitized! Beautiful and comfortable residence with Private Pool, Jacuzzi and Grill. 12min from Palmas del Mar that has beach, bars, night life and sea food restaurant. Minutes from Palma Real Mall, Walmart, restaurants, fast food & much more. 20 min from El Malecon de Naguabo which has many Seafood Restaurants, and beach. 30min to the boat terminal to go to Vieques and Culebra, 40 min from Luquillo Kiosk, 35 min from the Croabas, 45 min to the airport, 50 min to Old San Juan

Top guest favourite
Flat in Fajardo
4.94 out of 5 average rating, 115 reviews

Huge Salt Pool|Marina Escape|Ocean Views

A tranquil getaway in this stunning apartment with breathtaking ocean views. Step inside to discover modern updates & stylish design. The exclusive 2 suites feature beautiful windows, offering unobstructed view Unwind by the giant pool or enjoy the sunrise from the expansive balcony—perfect spots for relaxation. The fully equipped kitchen with exotic white granite countertops is ideal for whipping up meals. This is the perfect retreat for those seeking luxury & serenity!

Popular amenities for Roosevelt Roads rentals with a pool

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Quick stats about holiday rentals with a pool in Roosevelt Roads

  • Total holiday rentals

    Explore 90 holiday rentals in Roosevelt Roads

  • Nightly prices starting at

    Roosevelt Roads holiday rentals start at £30 per night before taxes and fees

  • Verified guest reviews

    Over 3,980 verified reviews to help you choose

  • Family-friendly holiday rentals

    90 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    90 of Roosevelt Roads holiday rentals include wifi 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!

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