
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-Private Couple Escape 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.

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!

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>

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!

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.

The Rising Sun - Private Island Getaway
Wake up in paradise! Enjoy your morning coffee on the balcony with a spectacular view. This apartment is located on a private island, 5 minutes off the coast of Fajardo, reached via ferry which is included. Fully equipped complex with 2 pools, basketball court, volleyball court, tennis court, picnic areas and laundry. Get ready to enjoy breath taking sunrises and sunsets from the large balcony!

Marina's view lll
Keep it simple at this peaceful and centrally-located place. This one bedroom apartment is fully furnished and remodeled with all the accommodations you need to have a great time in the east of Puerto Rico. Many beaches, restaurants and just minutes away. The complex has a huge pool, laundromat, basketball court and a playground. Feel free to reach us anytime. Have fun!
Popular amenities for Roosevelt Roads rentals with a pool
House rentals with a pool

Amazing Infinity pool @Coqui Tropical House

Renald's Place

Fajardo, Las Croabas

Lake and Beach Village, Humacao

Casa Domirriqueña privada playa Vieques, Culebra

Surf Side, Private Salt Water Pool, Ocean View

Renovated Beach House on BEST beach in Puerto Rico

Yunque Mar Beach House
Condo rentals with a pool

Hermoso apartamento frente al mar Ocean Blue Love❤️

Ocean View Luxury Condo

*Azul Marino* Golf & Ocean View Luxury Condo

Waterfront condo w/balcony, pool, minutes to beach

Villa @ Marina; Near Beach/Easy Access to Islands

Aqua Blue- Breathtaking Oceanview at Las Croabas

Breathtaking Ocean View Apartment

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

Casa Bella, Safe Harbor Marina Next to Ferry Ceiba

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

Ceiba Retreat #1

NEW! The Casitas Village

Starfish Ceiba, Entire home with private pool!

Sunrise Oasis apt #6

Del Mar y Sol - Vacation Your Way

Terraza del Sol in Ceiba! Ferry, Puerto del Rey.
When is the best time to visit Roosevelt Roads?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$31,568 GYD | G$30,523 GYD | G$30,523 GYD | G$31,359 GYD | G$30,104 GYD | G$29,895 GYD | G$31,359 GYD | G$30,941 GYD | G$28,850 GYD | G$27,178 GYD | G$29,059 GYD | G$31,359 GYD |
| 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 G$8,362 GYD 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!
Destinations to explore
- Punta Cana Vacation rentals
- San Juan Vacation rentals
- Santo Domingo Vacation rentals
- Las Terrenas Vacation rentals
- Santo Domingo Este Vacation rentals
- La Romana Vacation rentals
- Bayahibe Vacation rentals
- Juan Dolio Vacation rentals
- Carolina Vacation rentals
- Culebra Vacation rentals
- Saint Thomas Vacation rentals
- Saint Croix Vacation rentals
- Rentals with a patio Roosevelt Roads
- Fitness-friendly rentals Roosevelt Roads
- Pet-friendly rentals Roosevelt Roads
- Condo rentals Roosevelt Roads
- Rentals with beach access Roosevelt Roads
- Rentals with outdoor seating Roosevelt Roads
- Family-friendly rentals Roosevelt Roads
- Apartment rentals Roosevelt Roads
- House rentals Roosevelt Roads
- Rentals with a washer and dryer Roosevelt Roads
- 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
- Sun Bay Beach
- Cond Marina Lanais
- Balneario de Luquillo




