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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
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.
Apartment in Machos
4.89 out of 5 average rating, 199 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!

Top 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
4.99 out of 5 average rating, 293 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 favourite
An open rooftop terrace is presented, featuring a modular outdoor couch in neutral tones and a glass dining table surrounded by four black wicker chairs. A stylish area rug anchors the space, enhanced by plants and an awning that provides shade.
Apartment in Ceiba, Fajardo
4.97 out of 5 average rating, 231 reviews

Private Rooftop|Ferry&Marina|Airport| Power Backup

This amazing 2-story Penthouse offers breathtaking views of Culebra and Vieques Islands. With 3 bedrooms, 2 bathrooms, a rooftop terrace, and the exclusive distinction of being the only property in the community with a reliable power backup system, it provides all the comforts and conveniences you need. Located near Marina Puerto del Rey, Ceiba Airport, and the Ceiba Ferry Terminal; it definitely offers easy access to a variety of exciting activities. Create unforgettable family memories!

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, 173 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 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, 124 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, 163 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 favourite
A serene pool area is surrounded by manicured landscaping and swaying palm trees. Lounge chairs are positioned near the water, and a tall structure provides a backdrop with distinct architectural features. The clear blue water reflects the bright sky, creating a tranquil atmosphere.
Flat in Fajardo
4.88 out of 5 average rating, 138 reviews

Casita Jardín- Cozy 1 Bedroom Apt with Pool

Beautiful Garden View apartment located in a luxurious colorful village. Come enjoy this amazing apartment equipped with all the amenities you need for a fun, relaxing and romantic getaway. De-stress in our village’s pool and hot tub facilities just steps from the villa. Unwind with a good book on our balcony chaise lounge chairs or disconnect into nature in round of golf in El Conquistador’s beautiful golf course amenities. You will never want to leave. *No Pets Allowed*

Superhost
A modern gray sectional sofa is placed against a wall, featuring a light blue accent pillow. Sunlight gently filters through the nearby window, illuminating the comfortable seating area. A minimalist artwork is displayed above the sofa, complementing the room's neutral color scheme.
Apartment in Ceiba
4.85 out of 5 average rating, 197 reviews

The East Point P.R. Ceiba-Fajardo-Bio Bay- Yunque

Welcome to Puerto Rico eastern side. Our cozy shack is located near Seven Seas Beach (like 12min.), Rooselvet Roads Naval Base (15 min.), Vieques and Culebras Island Ferry Port (we can help you purchase tickets in advance and transportation) Luquillo, s Kioskos and Beach, El Yunque and Zipline (20 minutos) and Old San Juan (50min.) Our apartment is within a complex composed of 3 pools, half a basketball court, jungle gym and is a gate community with adequate security.

Top guest favourite
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, 266 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 favourite
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.
Apartment in Machos
4.93 out of 5 average rating, 100 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.

Guest favourite
A small balcony is showcased with two lounge chairs positioned near a glass railing, offering views of the surrounding hills. Green plants are arranged in planters, contributing to a relaxed atmosphere. Large sliding doors provide access and allow natural light to fill the space.
Apartment in Fajardo
4.9 out of 5 average rating, 183 reviews

Marina’s ll ocean view apartment

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 activities just minutes away. The complex has a huge pool, laundromat, basketball court and a playground. Feel free to reach us anytime. Have fun!

Top guest favourite
A modern studio apartment features a comfortable gray sofa adorned with striped pillows. A large wall-mounted TV provides entertainment options. Glass sliding doors offer a view of the ocean, while a semi-private sleeping area with a queen bed is visible in the background.
Flat in Fajardo
4.98 out of 5 average rating, 105 reviews

Oceanfront, new remodeled studio

Escape to a spectacular new remodeled, recently renovated and fully equipped oceanfront studio. A place to relax, retreat, reset and enjoy a beautiful experience. Located in the northeast coast of Fajardo, Puerto Rico and close to beautiful beaches, water activities, restaurants and touristic places.

Popular amenities for Roosevelt Roads rentals with a pool

When is the best time to visit Roosevelt Roads?

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Avg. price$195 SGD$188 SGD$188 SGD$193 SGD$186 SGD$184 SGD$193 SGD$191 SGD$178 SGD$164 SGD$164 SGD$193 SGD
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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 $52 SGD 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!