
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.

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 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!

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.

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.

El Yunque House: Private Pool & River
Casa el Yunque offers a serene retreat nestled within the breathtaking landscapes of El Yunque National Rainforest. With two cozy rooms and AC, one bathroom with hot water, and a refreshing pool 5 feet deep, The house has solar panels and a water tank. Enjoy nature's tranquility with a nearby private river, perfect for relaxation or adventure. The deck offers a beautiful spot for and outdoor dining. Experience the ultimate getaway at Casa el Yunque, where nature meets luxury.

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
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 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

Casa Blanca with pool, tropical garden and rooftop

Renald's Place

Fajardo, Las Croabas

Lake and Beach Village, Humacao

El Yunque Paradise - Private pool

Renovated Beach House on BEST beach in Puerto Rico

Hacienda Azucena, Rio Grande, El Yunque Rain Forest

Between sea and mountain El Yunque
Apartment rentals with a pool

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

Aqua Salada - Window 22, with Ocean/Marina View

Ocean View Luxury Condo

Lovely Ocean View Apartment

*Azul Marino* Golf & Ocean View Luxury Condo

Villa @ Marina; Near Beach/Easy Access to Islands

Panoramic Ocean View - Charm of the Sea

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

Apartment with Ocean View near Ceiba FerryTerminal

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

Starfish Ceiba, Entire home with private pool!

Costa Brava

Respir@ Villa Activities

Del Mar y Sol - Vacation Your Way

Spacious 3-Bedroom apartment with ocean view

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 | € 129 | € 124 | € 124 | € 128 | € 123 | € 122 | € 128 | € 126 | € 118 | € 108 | € 108 | € 128 |
| 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 € 34 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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- Rentals with pools Ceiba
- Rentals with pools Puerto Rico
- 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
- Balneario de Arroyo
- Punta Guilarte Beach
- The Saint Regis Bahia Golf Course




