
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.

Enchanted Pool Beach House
Take it easy at this tropical and peaceful getaway with a private pool where is only for the guest staying at the house. The house is 5 minutes away from many beaches like La Pared Beach, Playa Azul, Costa Azul Beach, Balneario La Monserrate Luquillo and Northeast Ecological Corridor. 10 minutes away from Bioluminescent Bay and Seaven Seas Beach in Fajardo. Also 15 minutes away from El Yunque National Forest in Rio Grande and 5 minutes from Caribbean Cinemas Theater, Shopping mall and Pharmacy.

Oceanview VistaBahía 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!

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!

Luxury Ocean Front Studio
Luxurious beachfront apartment to spend a beautiful day. It is located next to the Hotel El Conquistador with an incredible view. With a view to the sea, you can see Palomino Island, Icaco Cay, Island Culebra and Vieques. This apartment is unique, romantic and elegant to have a good time. It has different attractions nearby such as the Yunque, Seven Seas Beach,Snorkel and beach tours, Ferry to Culebra and Vieques. Different areas for night activities such as the Bio Bay in the Croabas.

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

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.

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.

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.

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!

Casa Génesis
Pasa tiempo de calidad junto a tu familia en un espacio relajante. El hospedaje te permite disfruta de un día caluroso en una piscina refrescante. Su ubicación le da la oportunidad de explorar las bellezas del Este de la isla. Cerca de la residencia se encuentran diversas atracciones y entre estas puedes encontrar el río Las tinajas, río El Hippie, Balneario Seven Seas, playa Los Machos, Ceiba Ferry Terminal, Marina Puerto del Rey, Las Croabas…

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.

Tierra Linda TreeHouse Private Pool & River
🏡Escape to Tierra Linda Treehouse, a romantic nature retreat in Río Grande. Enjoy a unique treehouse stay with a private pool, gas BBQ, air conditioning, and a beautiful river view. Perfect for couples seeking privacy, comfort, and a connection with nature. ✨
Popular amenities for Roosevelt Roads rentals with a pool
House rentals with a pool

Amazing Infinity pool @Coqui Tropical House

Saltwater pool+near beaches amazing home

Renald's Place

Fajardo, Las Croabas

Beautiful House, 24/7 Security, Gated Community

Casa La Piña Puerto Rico!

Casita Domirriqueña

El Yunque Paradise -Private pool
Condo rentals with a pool

Ocean Front Lovely 1-bedroom condo with pool

Aqua Salada Window 27, with Ocean/Marina View

Ocean View Luxury Condo

Marina’s ll ocean view apartment

Waterfront condo w/balcony, pool, minutes to beach

Villa @ Marina; Near Beach/Easy Access to Islands

Lux BEACH FRONT 19th Floor 1BR w/Pool & PK

Luxury Ocean View Apt 2 BR/1BA Dos Marinas Fajardo
Other vacation rentals with a pool

Fruit Farm Retreat NEW Pool & Views

Apartment with Ocean View near Ceiba FerryTerminal

Private Island | 1BR Condo | Oceanview | AC | WiFi

Modern 3/2 Apt near Marina Puerto Del Rey & Ferry

Costa Brava

Stylish Escape Private Pool near Ferry and Beach

Del Mar y Sol - Vacay Your Way

Sea Breeze Escape | Sleeps 7 + Pool in Ceiba
When is the best time to visit Roosevelt Roads?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ555 | ﺩ.ﺇ536 | ﺩ.ﺇ536 | ﺩ.ﺇ551 | ﺩ.ﺇ529 | ﺩ.ﺇ525 | ﺩ.ﺇ551 | ﺩ.ﺇ544 | ﺩ.ﺇ507 | ﺩ.ﺇ466 | ﺩ.ﺇ466 | ﺩ.ﺇ551 |
| Avg. temp | 25°C | 25°C | 26°C | 27°C | 28°C | 28°C | 28°C | 29°C | 29°C | 28°C | 27°C | 26°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 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!
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- Flamenco Beach
- Honeymoon Beach
- Limetree Beach
- Magens Bay Beach
- Liquillo Beach
- Distrito T-Mobile
- Playa de Luquillo
- Playa del Dorado
- Coco Beach Golf Club
- Rio Mar Village
- Toro Verde Adventure Park
- Playa de Cerro Gordo
- Carabali Rainforest Park
- Playa Maunabo
- Playa Puerto Real
- La Pared Beach
- Punta Bandera Luquillo PR
- Playa El Convento
- Mandahl Bay Beach
- Hull Bay Beach
- Balneario Condado
- Stream Thermal Bath
- Punta Guilarte Beach
- The Saint Regis Bahia Golf Course




