
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 $76 SGD 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.

Fabulous Ocean Views /Private Infinity Pool /4 BR
Relax at this spacious home with a private heated infinity pool with swim-up bar! With fabulous ocean and rainforest views from two covered decks, this house is family-friendly in a safe gated community only 5 minutes from Luquillo Beach and 15 minutes from the Rainforest. Other nearby activities include world-class golf, bio-bay kayaking, jet skis, ATV, horseback riding, go-karts, snorkeling, scuba diving, ziplining, great restaurants & a casino. Community pool, basketball & tennis courts too!
FamilyLocationAir conditioning

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.
FamilyValueIndoor spaces

Casa Familiar con Piscina en malecón de Naguabo
Disfruta de un alojamiento privado y completamente cercado, ideal para compartir con familia y amigos con total comodidad y seguridad. 🚗 A solo 30 segundos del Malecón, con una gran variedad de los mejores restaurantes 🏖️ A 2 minutos de la playa Fanduca 🎯 Amenidades: 🏊 Piscina privada 🎱 Billar 🤸 Trampolín 🧸 Columpio 🚗 Estacionamiento 📶 WiFi 🏀 Baloncesto 🏐 Volleyball Diversión garantizada. Ven a crear momentos inolvidables con tu familia en nuestra hermosa isla de Puerto Rico 🇵🇷
FamilyLocationParks

Casa Playa Tropical, Terraza y Piscina Unidas
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, Siempre tenemos agua potable en nuestra propiedad, para entral hay una cajita de seguria con llave
FamilyValueAir conditioning

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!
LocationValueSleep quality

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.
FamilyValueQuiet

Casa Mami y Papi including private suite
Bring your family and friends to this gated home wih beautiful views of the islands and Caribeen Sea. Minutes from beautiful beaches like Seven Seas (7 miles), and El Yunque Rainforest (8.8 miles), surfing at La Pared (9.4 miles), Boat trips from Puerto Del Rey (2 miles). For nightlife and shopping the Luquillo Kiosks offer 60 open air businesses with food, drinks (7.8 miles). The famous Laguna Grande Bio Bay in Fajardo is just (7.6 miles) away. Ferries to Vieques and Culebra (3 miles).
LocationFamilyAccuracy

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
FamilyLocationWifi

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.
LocationFamilyBack garden

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.
LocationFamilyLong stay

Ocean View Luxury Condo
My wife and I took great time to remodel our apt considering that we were sold on the High floor ocean view, the moonlight view at night, overlooking the marina, and beautiful mountains overlapping the ocean.Our balcony, off course, is our favorite location, where we hear the sound of the waves, the boats in and out of the marina,the manaties on the water, and the breathtaking winds on both sides of your apt.The apt is very romantic and family oriented at the same time.
ValueLocationCleanliness

ONE STOP VACATION HOME, w private pool and jaquzzi
ONE STOP VACATION HOMES OFFERS PRIVATE POOL W/ JACUZZI If you are looking for a place where you can relax at the private pool and entertain with family or a few friends at a beautiful place, !your search ends here!. This great property which is located just a few minutes from Seven Sea Beach, Las Croabas, Biobay, Scuba diving, El Yunque Rain Forest, Zipline at the Rain Forest, ATV Riding at Carabali, Luquillo Kioskos and Luquillo Beach.
ValueFamilyHot tub
Popular amenities for Roosevelt Roads rentals with a pool
House rentals with a pool

Renald's Place
ValueLocationDecor

5 bedroom Exclusive Beach Villa- WOW!
ValueLocationBiking

Hacienda Azucena, Río Grande, Yunque Rain Forest
ValueFamilyView

Casa Tesoro-pool home. Walk to beaches/restaurants
LocationFamilyLong stay

Amazing Infinity pool @Coqui Tropical House
ValueLocationCondition

Beautiful Getaway Home | Private Pool | 4BD
ValueLocationAmenities

Fajardo, Las Croabas
LocationValueHiking

Comfortable full house in a peaceful ambience.
FamilyValueLaundry
Apartment rentals with a pool

Beachfront Luxury Apartment w/ Amazing Views
LocationValueBack garden

New! Breath Taking View at Las Casitas Village
FamilyLocationCheckout

Oceanview Penthouse / Private Rooftop • Near Ferry
LocationValueParking

Pristine 4 bdrm (all private) steps to beach/golf
ValueLocationPool

Oceanview VistaBahía Penthouse Beach/Marina/Ferry
FamilyValueCheckout

Private Rooftop|Ferry&Marina|Airport| Power Backup
LocationValueCondition

Fajardo PR Modern Oceanfront Condo Million $ Views
LocationValuePool

Blue Pearl-1 Beachfront Retreat@Playa La Pared
FamilyLocationTV
Other holiday rentals with a pool

Casa Suiza-Private Couple Escape with Heated Pool
ValueLocationNearby

HERMOSA CASA CON PISCINA PRIVADA EN EL YUNQUE
ValueLocationLaundry

Ocean Bliss Oceanfront view apartment
ValueLocationNearby

Beachfront Luxury @ Wyndham Rio Mar Resort
FamilyLocationNearby

Hacienda Torres Paradise of Nature - Villa Limon
FamilyLocationHospitality

Mountain-to-Ocean Views • Private Luxury Retreat
ValueLocationKitchen

Vistamar- Stunning Ocean views & private pool!
FamilyValueRiver

Romantic Chalet with Pool by the River
ValueFamilyNearby
When is the best time to visit Roosevelt Roads?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $171 SGD | $177 SGD | $177 SGD | $181 SGD | $174 SGD | $172 SGD | $190 SGD | $187 SGD | $175 SGD | $165 SGD | $176 SGD | $190 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 |
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
- Flamenco Beach
- El Yunque National Forest
- Liquillo Beach
- Playa las Picuas, Rio Grande
- Puerto Rico Convention Center
- Distrito T-Mobile
- Rio Mar Village
- Magens Bay Beach
- La Pared Beach
- José Miguel Agrelot Coliseum
- Cond Marbella del Caribe Este
- Playa de Luquillo
- Honeymoon Beach
- Punta Bandera Luquillo PR
- Plaza Las Americas
- Limetree Beach
- San Patricio Plaza
- Isla Verde Beach West
- Isla Palomino
- Museo de Arte de Puerto Rico
- Balneario de Luquillo
- Cond Ashford Imperial
- Hacienda Campo Rico
- Cond Marina Lanais





