
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.

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!

Private Rooftop|Ferry&Marina|Airport| Power Backup
This amazing 2-story Penthouse offers breathtaking views of Culebra and Vieques Islands. With 3 bedrooms, 2 bathrooms, a rooftop terrace, and the exclusive distinction of being the only property in the community with a reliable power backup system, it provides all the comforts and conveniences you need. Located near Marina Puerto del Rey, Ceiba Airport, and the Ceiba Ferry Terminal; it definitely offers easy access to a variety of exciting activities. Create unforgettable family memories!

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.

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.

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.

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.

Marina’s ll ocean view apartment
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 activities just minutes away. The complex has a huge pool, laundromat, basketball court and a playground. Feel free to reach us anytime. Have fun!

Oceanfront, new remodeled studio
Escape to a spectacular new remodeled, recently renovated and fully equipped oceanfront studio. A place to relax, retreat, reset and enjoy a beautiful experience. Located in the northeast coast of Fajardo, Puerto Rico and close to beautiful beaches, water activities, restaurants and touristic places.
Popular amenities for Roosevelt Roads rentals with a pool
House rentals with a pool

Amazing Infinity pool @Coqui Tropical House

Casa Blanca with pool, tropical garden and rooftop

Renald's Place

Fajardo, Las Croabas

Lake and Beach Village, Humacao

Casa Domirriqueña privada playa Vieques, Culebra

El Yunque Paradise - Private pool

Renovated Beach House on BEST beach in Puerto Rico
Apartment rentals with a pool

Beautiful oceanfront apartment Ocean Blue Love❤️

Brisa Fresca, Apartment Luquillo PR!

Ocean View Penthouse Condo with A/C in every Room

The ReFresh | Warm minimalist seaviewing retreat

Lovely 2-2 Condo with the best view of Puerto Rico

Luquillo, Playa Azul Beach Front Apt 20th floor.

Fajardo PR Modern Oceanfront Condo Million $ Views

7th Floor View of Paradise
Other holiday rentals with a pool

Casa Bella, Safe Harbor Marina Next to Ferry Ceiba

Apartment with Ocean View near Ceiba FerryTerminal

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

The Escape House | Condo in Ceiba

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

Costa Esmeralda #1, Ceiba, Puerto Rico

NEW! Las Casitas Village

Oceanfront | Newly Remodeled | Stunning 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 | $195 SGD | $188 SGD | $188 SGD | $193 SGD | $186 SGD | $184 SGD | $193 SGD | $191 SGD | $178 SGD | $164 SGD | $164 SGD | $193 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 3,980 verified reviews to help you choose

Family-friendly holiday rentals
90 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!
Destinations to explore
- Punta Cana Holiday rentals
- San Juan Holiday rentals
- Santo Domingo Holiday rentals
- Las Terrenas Holiday rentals
- Santo Domingo Este Holiday rentals
- La Romana Holiday rentals
- Bayahibe Holiday rentals
- Juan Dolio Holiday rentals
- Carolina Holiday rentals
- Culebra Holiday rentals
- Saint Thomas Holiday rentals
- Saint Croix Holiday rentals
- Pet-friendly rentals Roosevelt Roads
- Apartment rentals Roosevelt Roads
- Rentals with beach access Roosevelt Roads
- Rentals with outdoor seating Roosevelt Roads
- Family-friendly rentals Roosevelt Roads
- Fitness-friendly rentals Roosevelt Roads
- Rentals with a washing machine and dryer Roosevelt Roads
- Flat rentals Roosevelt Roads
- House rentals Roosevelt Roads
- Rentals with a patio Roosevelt Roads
- Rentals with pools Ceiba
- Rentals with pools Puerto Rico
- Flamenco Beach
- Honeymoon Beach
- Limetree Beach
- Magens Bay Beach
- Plaza Del Mercado De Santurce
- Liquillo Beach
- Distrito T-Mobile
- Puerto Rico Convention Center
- Playa de Luquillo
- José Miguel Agrelot Coliseum
- Rio Mar Village
- Toro Verde Adventure Park
- Carabali Rainforest Park
- Punta Bandera Luquillo PR
- La Pared Beach
- Museo de Arte de Puerto Rico
- Balneario del Escambrón
- Isla Verde Beach West
- Isla Palomino
- Las Paylas
- Sun Bay Beach
- Playa las Picuas, Rio Grande
- Balneario de Luquillo
- Plaza Las Americas




