
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.

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 * * *

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!

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.

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.

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.

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 Corona - Amazing Views, Pool, Close to Beach
Experience this newly renovated home with constant ocean breezes and breathtaking views of the Corona Reef, Culebra and the "Big Island." This cozy cottage offers 'casual luxury' with premium furnishings and cool, comfortable linens and fabrics. Enjoy the ocean-facing plunge pool and outdoor shower. Located just past the former W Resort on a private fenced/gated lot that's minutes from everything (airport, ferry, restaurants, beaches and shopping).

Casa Génesis
Spend quality time with your family in a relaxing space. The accommodation allows you to enjoy a hot day in a refreshing pool. Its location gives you the opportunity to explore the beauty of the island's east. Near the residence are various attractions and among these you can find the Las Tinajas River, El Hippie River, Seven Seas Spa, Los Machos Beach, Ceiba Ferry Terminal, Puerto del Rey Marina, 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.

Ocean Front Resort Villa
A luxurious and tranquil cliffside retreat overlooking the endless ocean. Elegant casitas with breathtaking views, ultimate privacy, 3 sparkling pools including an infinity edge, and a soothing jacuzzi. Close to pristine beaches, water adventures, and the ferry to Culebra.
Popular amenities for Roosevelt Roads rentals with a pool
House rentals with a pool

Amazing Infinity pool @Coqui Tropical House

Renald's Place

Casa La Piña Puerto Rico!

Lake and Beach Village, Humacao

Domirriqueña House

Between sea and mountain El Yunque

Casa Amor Home Esperanza Salt Pool- close to Beach

❤️PRIVATE POOL,Beach home,BioBay Tour walk distance
Apartment rentals with a pool

Ocean Front Lovely 1-bedroom condo with pool

Oceanfront Gem • Pool • High-Floor Sea Views

Gorgeous Ocean views studio, beachfront property!

Aqua Salada - Window 22, with Ocean/Marina View

Waterfront High-Rise Apt with Gorgeous Ocean View

Marina’s ll ocean view apartment

Caribbean Beachfront King bed with large balcony

Breathtaking Ocean View Apartment
Other holiday rentals with a pool

Fruit Farm Retreat NEW Pool & Views

Apartment with Ocean View near Ceiba FerryTerminal

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

Costa Esmeralda #1, Ceiba PR

Cielo Studio tranquility w/pool in rural location

At The Waves - Ocean Front Villa 1 bed/1 bath unit

Private Pool Bar with Panoramic View! 5* A/C, WiFi

Costa Brava
When is the best time to visit Roosevelt Roads?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $197 SGD | $191 SGD | $191 SGD | $196 SGD | $188 SGD | $187 SGD | $196 SGD | $193 SGD | $180 SGD | $166 SGD | $166 SGD | $196 SGD |
| 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 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 4,290 verified reviews to help you choose

Family-friendly holiday rentals
80 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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