
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.

1BR/W - Spectacular Ocean View/Pool/Walk to Beach
"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!

Vista Linda Haus
At Vista Linda Haus, from the moment you start the journey to the beautiful town of Gurabo, the adventure begins. A unique experience towards the favorite destination. You will find panoramic landscapes, lakes, mountains, farms, cities, and a community with the Puerto Rican warmth of our mountains. Just 35 minutes from the Luis Muñoz Marín International Airport, over 1,000 feet above sea level, you will breathe freedom and peace, in a harmonious environment full of energy and pure nature.

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.

Oceanfront Relaxation | High-Floor w/ Views & Pool
Wake up to stunning Caribbean sunrises and fall asleep to the gentle sound of ocean waves at this oceanfront escape in Fajardo. Located in a quiet, gated community with a pool and free Wi-Fi, this 1-bedroom condo features a queen bed, sofa bed, full bathroom, and panoramic ocean views. You're just minutes from El Yunque, island ferries, fresh seafood, and local shops. Whether you’re seeking adventure or pure relaxation, your perfect getaway starts here—book now and experience paradise!

Casa Borinquen
This homey vacation rental is a brand new construction and is a great place to enjoy the outdoors. The interiors feature a modern design, a full kitchen, full bathroom, outdoor shower, and sleeps 3 people. Listen to the sound of the coquis at night and enjoy the tropical breve e, relaxing in the beautiful plunge pool or grilling on the outdoor deck, surrounded by lush palms, fruit trees (breadfruit, lemons, bananas, plantains, cashews), and herbs (mint, sweet peppers, oregano).

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.

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 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…
Popular amenities for Roosevelt Roads rentals with a pool
House rentals with a pool

Amazing Infinity pool @Coqui Tropical House

Local charm, private oasis nearby amenities.

Beautiful Getaway Home | Private Pool | 4BD

Villa Estrella PR (near Airport & Beach)

Fajardo, Las Croabas

Renovated Beach House on BEST beach in Puerto Rico

Between sea and mountain El Yunque

Fabulous Ocean Views /Private Infinity Pool /4 BR
Condo rentals with a pool

Ocean Front Lovely 1-bedroom condo with pool

Brisa Fresca, Apartment Luquillo PR!

🌟Delightful Panoramic View at Marina's Getaway I 🌟

Aqua Salada - Window 22, with Ocean/Marina View

Lovely Ocean View Apartment

Harry & Maddie’s Beach Getaway

Villa @ Marina; Near Beach/Easy Access to Islands

Lux BEACH FRONT 19th Floor 1BR w/Pool & PK
Other vacation rentals with a pool

Apartment with Ocean View near Ceiba FerryTerminal

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

Casita Jardín- Cozy 1 Bedroom Apt with Pool

NEW! The Casitas Village

Costa Brava

Del Mar y Sol - Vacation Your Way

Spacious 3-Bedroom apartment with ocean view

Baycay Suite | Ocean, Mountain and Marina Views
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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