
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.

Casa Suiza - Couple Retreat with Heated Pool
Casa Suiza es un lugar para escapadas románticas, sólo para parejas con Piscina Climatizada. Estamos en la montaña, es muy privado, alejado de la ciudad, a una hora de distancia de San Juan y el Aeropuerto Internacional de Puerto Rico. En su beneficio, una vez comience a subir a la montaña, es por calles con curvas y algunas pendientes empinadas, pero completamente transitables. Recomendamos rentar un vehículo SUV o 4x4 para su tranquilidad, si no está acostumbrado a transitar en la Montaña.

Oceanfront Gem • Pool • High-Floor Sea Views
Discover the best of Fajardo in this oceanfront gem—where each day begins with breathtaking Caribbean sunrises and ends to the soothing sound of waves. Nestled in a peaceful, gated community with a pool and free Wi-Fi, this 1-bedroom retreat offers a queen bed, full bath, and sweeping ocean views. Just minutes from El Yunque, beaches, island ferries, seafood spots, and shops. Whether you're here to relax or explore, your perfect tropical escape starts here—book now and make it unforgettable!

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.

Mountainside Ocean View Pool/Family Fun Ferry
Experience Puerto Rico's rainforest at our mountaintop apartment. Coqui's and owls create a natural background at night. 1 full apartment including garage parking. Full kitchen, full bedroom, living room converts to a queen bed. 18' pool with ocean view 12' gazebo. 3 acres of trails to hike, trampoline, and zip line for children. kayak and beach equipment. transportation to ferry available. Our boat is also available seek a water adventure. very kid friendly - must be ok with dogs.

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.

Oceanfront Oasis: Panoramic Views & Marina Access
Charming studio with breathtaking views, located in Fajardo on the stunning east coast of Puerto Rico, just 45 minutes from San Juan. This is the perfect romantic escape from the everyday routine, ideal for up to Two Guests. If your group exceeds two, we invite you to explore our second property with two bedrooms. Enjoy pristine beaches, top tourist attractions, and fantastic dining options nearby. Plus, you're just 20 minutes from the ferry to Culebra or Vieques islands!<br><br>

Casita Jardín- Cozy 1 Bedroom Apt with Pool
Beautiful Garden View apartment located in a luxurious colorful village. Come enjoy this amazing apartment equipped with all the amenities you need for a fun, relaxing and romantic getaway. De-stress in our village’s pool and hot tub facilities just steps from the villa. Unwind with a good book on our balcony chaise lounge chairs or disconnect into nature in round of golf in El Conquistador’s beautiful golf course amenities. You will never want to leave. *No Pets Allowed*

The East Point P.R. Ceiba-Fajardo-Bio Bay- Yunque
Welcome to Puerto Rico eastern side. Our cozy shack is located near Seven Seas Beach (like 12min.), Rooselvet Roads Naval Base (15 min.), Vieques and Culebras Island Ferry Port (we can help you purchase tickets in advance and transportation) Luquillo, s Kioskos and Beach, El Yunque and Zipline (20 minutos) and Old San Juan (50min.) Our apartment is within a complex composed of 3 pools, half a basketball court, jungle gym and is a gate community with adequate security.

*Azul Marino* Golf & Ocean View Luxury Condo
Azul Marino is our spacious one bedroom overlooking the east coast of Puerto Rico. Located inside a 5 stars resort, you have a golf course, 2 pools, hot tubs and be near the main excursions of Puerto Rico. Be minutes away from the bioluminescent bay, take a catamaran to the islands and enjoy a entire day at the beach doing snorkeling or just relaxing. This apartment had a full size kitchen, enormous living room and a very confortable king size in the bedroom.

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

Renald's Place

Fajardo, Las Croabas

Beautiful House, 24/7 Security, Gated Community

Daddy’s Place Airbnb

Lake and Beach Village, Humacao

Surf Side, Private Salt Water Pool, Ocean View

Renovated Beach House on BEST beach in Puerto Rico

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

Ocean Front Lovely 1-bedroom condo with pool

Hermoso apartamento frente al mar Ocean Blue Love❤️

🌟Delightful Panoramic View at Marina's Getaway I 🌟

Ocean View Luxury Condo

Waterfront condo w/balcony, pool, minutes to beach

Villa @ Marina; Near Beach/Easy Access to Islands

Breathtaking Ocean View Apartment

Luquillo, Playa Azul Beach Front Apt 20th floor.
Other vacation rentals with a pool

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

The Escape House | Condo in Ceiba

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

Tropical Bliss * 10 min to Ferry~Pool~Beach~BBQ

Ceiba Retreat #1

High Rise Beachfront|Panoramic Views+Pool|Floor 24

Starfish Ceiba, Entire home with private pool!

Spacious 3-Bedroom apartment with ocean view
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.ﺇ477 | ﺩ.ﺇ510 | 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 3,980 verified reviews to help you choose

Family-friendly vacation rentals
90 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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- Rentals with pools Ceiba
- Rentals with pools Puerto Rico
- Flamenco Beach
- Honeymoon Beach
- Limetree Beach
- Magens Bay Beach
- Liquillo Beach
- Distrito T-Mobile
- Puerto Rico Convention Center
- Playa de Luquillo
- Playa las Picuas, Rio Grande
- José Miguel Agrelot Coliseum
- Rio Mar Village
- Carabali Rainforest Park
- Toro Verde Adventure Park
- La Pared Beach
- Punta Bandera Luquillo PR
- Museo de Arte de Puerto Rico
- Isla Verde Beach West
- Balneario del Escambrón
- Plaza Las Americas
- San Patricio Plaza
- Las Paylas
- Cond Marina Lanais
- Balneario de Luquillo
- Playita del Condado




