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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
Condo in Machos
4.9 out of 5 average rating, 194 reviews

Oceanview Vista Bahía Penthouse near 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 favourite
Villa in Luquillo
4.93 out of 5 average rating, 184 reviews

Hilltop Villa with Infinity Pool and Ocean View

Spacious two story, three bedroom house, with 2 full baths in the second story, one half bath in first story, rustic architecture, ceramic tile floors, fully air conditioned, with large kitchen and all appliances; back yard is very large, has an infinity pool (private) that blends with the North Atlantic Ocean ; outdoor amenities also include BBQ/grill area, various lounging areas, bar area with sink and lots of outdoor counter space, outdoor shower, two changing rooms, and covered garage.

Top Guest favourite
Tiny home in Fajardo
4.99 out of 5 average rating, 267 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
Condo in Ceiba, Fajardo
4.97 out of 5 average rating, 229 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!

Top Guest favourite
Guest suite in Luquillo
5 out of 5 average rating, 190 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 favourite
Home in Ceiba
4.99 out of 5 average rating, 106 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
Tiny home in Naguabo
4.99 out of 5 average rating, 148 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.

Top Guest favourite
Condo in Fajardo
4.96 out of 5 average rating, 356 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 favourite
Tiny home in Vieques
4.95 out of 5 average rating, 327 reviews

Esperanza Casita, Pool, Walk to Beach & Top Food

- Adults Only (18+) - Pool Hours 7am–7pm - Max 2 Adults (No Visitors) - Cold AC & Hot Water - New Queen Bed, TV, Microwave, Small Fridge - Beach Towels, Chairs, Snorkel Gear - No Pets / No Smoking - Small Bags Recommended (Big Bags Fit Under Bed) - Quiet Hours: 10pm–6am Just 1.5 blocks from beaches, top restaurants & music. Relax after a day in the sun or enjoy a night out. For 20+ years, Coco Loco has been the choice for the perfect adult getaway.

Top Guest favourite
Condo 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
Apartment in CEIBA
4.88 out of 5 average rating, 171 reviews

Hacienda Torres Paradise of Nature - Villa Limon

2 bedroom, 1 bathroom apartment in the middle of a 40 acre private property with peaceful ambiance. We have very friendly farm dogs that are loose and will interact with guests. You will be serenated by birds during the day and coquis at night! 5 min access to highway #53. Near beaches, marinas, restaurants, ferry to Culebra and Vieques islands and Roosevelt Roads Airport.

Guest favourite
Condo in Fajardo
4.9 out of 5 average rating, 102 reviews

Ocean Front Resort Villa

This is unique and tranquil getaway. Casitas are on a cliff facing open ocean with stunning views, yet very close to many attractions, ferry to Culebra, Beaches and water sports. las Casitas vullage is private property and hotel amenities are for their hotel guests only.

Popular amenities for Roosevelt Roads rentals with a pool

Quick stats about holiday rentals with a pool in Roosevelt Roads

  • Total rentals

    90 properties

  • Nightly prices starting at

    $61 AUD before taxes and fees

  • Total number of reviews

    4K reviews

  • Family-friendly rentals

    80 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace