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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
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, 166 reviews

Casa Suiza-Private Couple Escape with Heated Pool

Casa Suiza es un lugar para escapadas románticas, sólo para parejas con Piscina Climatizada. Estamos 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. En su beneficio, una vez comience a subir a la montaña, es por calles con curvas y algunas pendientes empinadas, pero completamente transitables. Recomendamos rentar un vehículo SUV o 4x4 para su tranquilidad, si no está acostumbrado a transitar en la Montaña.

Guest favorite
A vibrant sunrise casts warm hues over the ocean, framed by lush green palm fronds. The view extends over the coastal landscape, showcasing buildings and distant hills against the expansive horizon.
Condo in Machos
4.9 out of 5 average rating, 203 reviews

Oceanview Bay View Penthouse Beach/Marina/Ferry

Enjoy your island escape at "Vista Bahía Penthouse" in Costa Esmeralda. There is something special about Ceiba – sleeping away from the hustle and bustle of everyday life and only minutes away from multiple activities and places you will enjoy. 3 to 5 minutes to marina, beaches, restaurants, shopping, and more. Wake up to sunrises right outside your window. The condo features 3 bedrooms air-conditioned, kitchen with all the convenience. Relax on the private rooftop with ocean panoramic views!

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
4.98 out of 5 average rating, 301 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!

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.
Apartment in Ceiba
4.84 out of 5 average rating, 177 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.

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, 130 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.

Guest favorite
Condo in Fajardo
4.94 out of 5 average rating, 118 reviews

Oceanfront Oasis: Panoramic Views & Marina Access

Charming studio with breathtaking views, located in Fajardo on the stunning east coast of Puerto Rico, just 45 minutes from San Juan. This is the perfect romantic escape from the everyday routine, ideal for up to Two Guests. If your group exceeds two, we invite you to explore our second property with two bedrooms. Enjoy pristine beaches, top tourist attractions, and fantastic dining options nearby. Plus, you're just 20 minutes from the ferry to Culebra or Vieques islands!<br><br>

Top guest favorite
A bright pool area features colorful pool floats resting on the water's surface. A shaded outdoor seating area with comfortable furniture is visible alongside the pool. Lush greenery and mountain views are framed by the surrounding structures, creating an inviting space for relaxation.
Villa in Luquillo
4.98 out of 5 average rating, 138 reviews

Sun (Sky Sun Villas)

Sun Villa is the perfect place to rest, relax and enjoy the beautiful scenery offered by the Yunque Mountains, the Rain Forest, and on the other hand the sea. Here you can breathe fresh air, it is a relaxing place, for family, couples, friends and overall a safe place (Gated Community) . We are located in a central area were you can go to variety of beaches, rivers, rainforest, malls, pharmacies, restaurants that are no less than 5-20minutes away. Check our to do list guidebook.

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, 376 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, 272 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!

Top guest favorite
A modern living area features a black leather sofa, a circular coffee table, and a woven area rug. Natural light floods the space through large glass doors, leading to a balcony. A TV and workspace are also visible, complementing the contemporary design.
Condo in Machos
4.93 out of 5 average rating, 101 reviews

Ocean View Rooftop Condo Vista Azul Penthouse

Beautiful Ocean View Penthouse Apartment located in the East Side Coast of Ceiba Puerto Rico. The apartment is in a closed gated community with on site Security. There are 2 parking spaces available. Only 7 minutes away from the Ferry Terminal to Vieques and Culebra, 5 minutes away from playa Macho, about 20 minutes from Luquillo Kiosk and 30 minutes from the National Rainforest in Rio Grande.

Top guest favorite
A serene ocean view is captured, featuring a soft, colorful sky at sunset. Gentle waves lap at the shore, while palm trees sway in a lush green area dotted with red canopies, creating inviting spots for relaxation.
Condo in Fajardo
4.94 out of 5 average rating, 131 reviews

The Rising Sun - Private Island Getaway

Wake up in paradise! Enjoy your morning coffee on the balcony with a spectacular view. This apartment is located on a private island, 5 minutes off the coast of Fajardo, reached via ferry which is included. Fully equipped complex with 2 pools, basketball court, volleyball court, tennis court, picnic areas and laundry. Get ready to enjoy breath taking sunrises and sunsets from the large balcony!

Guest favorite
Condo in Fajardo
4.89 out of 5 average rating, 168 reviews

Marina's view lll

Keep it simple at this peaceful and centrally-located place. This one bedroom apartment is fully furnished and remodeled with all the accommodations you need to have a great time in the east of Puerto Rico. Many beaches, restaurants and just minutes away. The complex has a huge pool, laundromat, basketball court and a playground. Feel free to reach us anytime. Have fun!

Popular amenities for Roosevelt Roads rentals with a pool

When is the best time to visit Roosevelt Roads?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$31,568 GYDG$30,523 GYDG$30,523 GYDG$31,359 GYDG$30,104 GYDG$29,895 GYDG$31,359 GYDG$30,941 GYDG$28,850 GYDG$27,178 GYDG$29,059 GYDG$31,359 GYD
Avg. temp25°C25°C26°C27°C28°C28°C28°C29°C29°C28°C27°C26°C

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 G$8,362 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,980 verified reviews to help you choose

  • Family-friendly vacation rentals

    90 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!