
Holiday rentals with a pool in Roosevelt Roads
Find and book unique homes with a pool on Airbnb
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 £45 per night before taxes and fees

Verified guest reviews
Over 4,330 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!
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 Playa Tropical, Tropical Beach House & Pool
Ven y disfruta con toda la familia en esta espaciosa casa, TROPICAL BEACH HOUSE - CASA PLAYA TROPICAL. Casa frente a la playa, Único concepto con piscina bar unida a la terraza para un mejor deleite a los huespedes. Tres habitaciones totalmente equipadas, una con cama king y su baño privado otra con una cama matrimonial, una litera y otro bano y otra con otra cama matrimonial y otra litera, Tenemos un generador elecgrico de 40 kilos automatico, para entral hay una cajita de seguria con llave

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.

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!

Oceanview Penthouse / Private Rooftop • Near Ferry
Wake up to ocean views and unwind on your private rooftop in Puerto Rico’s beautiful east side — just 8 minutes from the Ceiba ferry to Vieques & Culebra. This spacious 3-bedroom, 2-bath penthouse is located in a gated community with on-site security, 2 free parking spaces, and a private rooftop perfect for sunrise coffee, stargazing, and relaxing after a beach day. Minutes from beaches, Luquillo kiosks, El Yunque, Las Croabas, and some of the best experiences on Puerto Rico’s east coast.

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.

Vieques ocean view eco villa+pool
-Privately nestled on three acres with Caribbean Sea views from the second floor. -Three private bedroom suites - mosquito nets. Villa doesn’t have Ac -Spa and yoga classes nearby at Finca Victoria -Full service amenities can be arranged: stocking the fridge, chef, massages. -Gunite swimming pool - solar powered -Each bedroom has its own bathroom, dressing area & outdoor shower -The beds are fitted with quality 400-count cotton linens - Strict no children under the age of 10years policy

Casa Suiza-Private Couple Escape with Heated Pool
Casa Suiza es un retiro de escapadas románticas, sólo para parejas con Piscina Climatizada. Estamos ubicados 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. Recomendamos rentar un vehículo SUV o 4x4 para su tranquilidad, si no está acostumbrado a transitar en la Montaña. Una vez comienzas a subir a la montaña, es por calles con curvas y algunas pendientes empinadas, pero completamente transitables.

Casa Escape Cerca del ferry(Vieques y culebra)
En CASA ESCAPE estarás cerca de todo. Encontrarás en el centro del pueblo varios negocios entre ellos restaurantes, panaderías, farmacias, banco y otras. Estarás a 8 min del Terminal del ferry Vieques y Culebra, 3 min de Playa Medio mundo , 3min de Marina Puerto del Rey, 15 min de Villa Marina, 20 min de las Croabas y playa Seven Sea, donde encontrar diversidad de restaurantes y actividades recreativas, 15 min de los kiosco y playa de Luquillo y 25 min del Yunque National Forestal.

Beautiful House, 24/7 Security, Gated Community
Sanitized! Beautiful and comfortable residence with Private Pool, Jacuzzi and Grill. 12min from Palmas del Mar that has beach, bars, night life and sea food restaurant. Minutes from Palma Real Mall, Walmart, restaurants, fast food & much more. 45 min to the airport, 50 min to Old San Juan. 20 min from El Malecon de Naguabo which has many Seafood Restaurants, and beach. 30min to the boat terminal to go to Vieques and Culebra, 40 min from Luquillo Kiosk, 35 min from the Croabas.

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.

Scenic Hideaway Ocean Views & Private Roof Deck
This scenic island hideaway, designed by acclaimed architect John Hix, is a serene oasis perched atop a breezy hill with breathtaking views of the Atlantic Ocean and the Caribbean Sea. The loft features a private rooftop terrace, open-air shower, well-equipped kitchen, high thread count sheets, oversized plush towels, strong WiFi, and a uniquely beautiful shared pool. Despite the privacy of the property, Vieques' best beaches, restaurants, and trail heads are minutes away.

Hilltop Cabin w/ Pool & Views – 18 Mins to Airport
✈️ 18 min to airport & 🏖️ top beaches 🏊 Private pool, loungers & hammocks 🌿 Peaceful countryside, just 5 min to city 🌴 45 min to El Yunque & Luquillo Beach 🏡 Hilltop cabin with ocean & mountain views 🛏 Queen bed + full pull-out bed (sleeps 4) 🍽 Indoor + outdoor dining for 4 with views 🚿 Outdoor shower (perfect after the beach) 🌅 Stunning sunrise views from elevated setting ⚡ Fast WiFi, A/C, Smart TV & gated parking 🪑 Beach chairs, cooler & beach towels
Popular amenities for Roosevelt Roads rentals with a pool
House rentals with a pool

Casa de Campo El Saco

Beachfront Villa surrounded by Ocean w/pool

Fajardo, Las Croabas

Renald's Place

Renovated Beach House on BEST beach in Puerto Rico

Hacienda Azucena, Río Grande, Yunque Rain Forest

Casa Amor Home Esperanza Salt Pool- close to Beach

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

Oceanview VistaBahía Penthouse Beach/Marina/Ferry

Beachfront Apt. Ocean-Facing Bed & City Views+Pool

Oceanfront Relaxation | High-Floor w/ Views & Pool

Ocean View Luxury Condo

Villa @ Marina; Near Beach/Easy Access to Islands

Our slice of paradise

Beachfront Luxury Apartment w/ Amazing Views

Fajardo PR Modern Oceanfront Condo Million $ Views
Other holiday rentals with a pool

Apartment with Ocean View near Ceiba FerryTerminal

Tierra Linda TreeHouse Private Pool & River

Luxury Villa 5340

Starfish Ceiba, Entire home with private pool!

The Sandcastle - A Seashore Haven - 1 bedroom apt.

Wake Up to Ocean Views | Pool + Marina Paradise

Villa Respira

Horizonte Cercano Penthouse/Ferry/Pool/Beach
When is the best time to visit Roosevelt Roads?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £101 | £105 | £105 | £112 | £108 | £107 | £112 | £111 | £103 | £97 | £104 | £112 |
| 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 |
Destinations to explore
- San Juan Holiday rentals
- Higüey Holiday rentals
- Punta Cana Holiday rentals
- Santo Domingo Este Holiday rentals
- Las Terrenas Holiday rentals
- Santo Domingo Holiday rentals
- Fajardo Holiday rentals
- La Romana Holiday rentals
- Ponce Holiday rentals
- Luquillo Holiday rentals
- Aguadilla Holiday rentals
- Dominicus Holiday rentals
- Family-friendly rentals Roosevelt Roads
- Apartment rentals Roosevelt Roads
- Rentals with beach access Roosevelt Roads
- Rentals with outdoor seating Roosevelt Roads
- Pet-friendly rentals Roosevelt Roads
- Rentals with a patio Roosevelt Roads
- Fitness-friendly rentals Roosevelt Roads
- Flat rentals Roosevelt Roads
- Rentals with a washing machine and dryer Roosevelt Roads
- House rentals Roosevelt Roads
- Rentals with pools Ceiba
- Rentals with pools Puerto Rico
- Flamenco Beach
- El Yunque National Forest
- Liquillo Beach
- Playa las Picuas, Rio Grande
- Distrito T-Mobile
- Magens Bay Beach
- Honeymoon Beach
- José Miguel Agrelot Coliseum
- La Pared Beach
- Playa de Luquillo
- Cond Marbella del Caribe Este
- Punta Bandera Luquillo PR
- Limetree Beach
- Plaza Las Americas
- San Patricio Plaza
- Isla Verde Beach West
- Museo de Arte de Puerto Rico
- Isla Palomino
- Balneario de Luquillo
- Cond Ashford Imperial
- Cond Marina Lanais
- Playita del Condado
- Plaza Del Mercado De Santurce
- Las Paylas





