
Vacation rentals with a pool in Roosevelt Roads
Find and book unique homes with a pool on Airbnb
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.ﺇ 220 per night before taxes and fees

Verified guest reviews
Over 4,330 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!
Top-rated rentals with a pool in Roosevelt Roads
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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.
FamilyValueCheckout
4.93 out of 5 average rating, 230 reviews
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!
LocationValueQuiet
4.96 out of 5 average rating, 156 reviews
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 🇵🇷
FamilyValueTV
4.93 out of 5 average rating, 329 reviews
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!
FamilyValueBeach
4.98 out of 5 average rating, 357 reviews
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.
LocationFamilyWalkability
4.93 out of 5 average rating, 115 reviews
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.
FamilyLocationCleanliness
4.98 out of 5 average rating, 162 reviews
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).
ValueLocationBackyard
4.95 out of 5 average rating, 103 reviews
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
FamilyLocationBreakfast
4.96 out of 5 average rating, 103 reviews
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.
LocationValueBackyard
4.93 out of 5 average rating, 128 reviews
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.
FamilyValueHospitality
4.92 out of 5 average rating, 317 reviews
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 para los huespedes. Tres habitaciones totalmente equipadas, al lado del Paseo El Malecon y a 12 minutes de Walmart y today las tiendas internacionales, Cerca de Todo., Siempre tenemos agua potable en nuestra propiedad, Para entral hay una cajita de seguridad con las llave.,
FamilyLocationOutdoor spaces
4.97 out of 5 average rating, 153 reviews
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.
ValueFamilyAmenities
4.9 out of 5 average rating, 353 reviewsPopular amenities for Roosevelt Roads rentals with a pool
House rentals with a pool

Piscina privada, playa cerca, Wifi, pet friendly
FamilyLocationDecor
4.93 out of 5 average rating, 101 reviews
Amazing Infinity pool @Coqui Tropical House
ValueFamilyCleanliness
4.98 out of 5 average rating, 127 reviews
Hacienda Azucena, Río Grande, Yunque Rain Forest
ValueFamilyIndoor spaces
4.95 out of 5 average rating, 197 reviews
Pool +near beaches, amazing home/Back up Water
FamilyLocationBackyard
4.98 out of 5 average rating, 136 reviews
5 bedroom Exclusive Beach Villa- WOW!
FamilyValueQuiet
4.95 out of 5 average rating, 152 reviews
Casita Paraíso
ValueLocationParking
4.96 out of 5 average rating, 268 reviews
Renald's Place
ValueFamilyBeach
4.92 out of 5 average rating, 181 reviews
Beautiful Getaway Home | Private Pool | 4BD
FamilyLocationDecor
4.93 out of 5 average rating, 172 reviewsCondo rentals with a pool

Oceanview VistaBahía Penthouse Beach/Marina/Ferry
ValueLocationDecor
4.89 out of 5 average rating, 235 reviews
Ocean View Luxury Condo
LocationFamilyBathroom
4.96 out of 5 average rating, 273 reviews
Beachfront Luxury Apartment w/ Amazing Views
ValueLocationQuiet
4.96 out of 5 average rating, 199 reviews
Las Casitas, Panoramic Ocean View – Fajardo, PR
LocationFamilyCheck-in
4.9 out of 5 average rating, 180 reviews
The Felix:Family friendly-pool-3minWalk2Beach-8ppl
LocationFamilyCleanliness
4.91 out of 5 average rating, 112 reviews
Private Rooftop|Ferry&Marina|Airport| Power Backup
LocationValueParking
4.97 out of 5 average rating, 244 reviews
Villa @ Marina; Near Beach/Easy Access to Islands
LocationValueBeach
4.95 out of 5 average rating, 130 reviews
Fajardo PR Modern Oceanfront Condo Million $ Views
LocationFamilyComfort
4.97 out of 5 average rating, 145 reviewsOther vacation rentals with a pool

HERMOSA CASA CON PISCINA PRIVADA EN EL YUNQUE
LocationValueKitchen
4.95 out of 5 average rating, 149 reviews
Mountain-to-Ocean Views • Private Luxury Retreat
LocationFamilyCondition
4.98 out of 5 average rating, 123 reviews
Ocean Bliss Oceanfront view apartment
FamilyLocationDecor
4.92 out of 5 average rating, 316 reviews
Wake Up to Ocean Views | Pool + Marina Paradise
FamilyLocationSleep quality
4.93 out of 5 average rating, 151 reviews
Vistamar- Stunning Ocean views & private pool!
LocationFamilyOutdoor spaces
4.94 out of 5 average rating, 157 reviews
Starfish Ceiba, Entire home with private pool!
LocationValueCleanliness
4.89 out of 5 average rating, 99 reviews
Rustic Retreat- El Yunque view, pool and game room
LocationFamilyLayout
4.96 out of 5 average rating, 54 reviews
4BR Country Escape with Pool & Mountain View’s
LocationFamilyComfort
4.92 out of 5 average rating, 12 reviewsWhen is the best time to visit Roosevelt Roads?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 496 | ﺩ.ﺇ 514 | ﺩ.ﺇ 514 | ﺩ.ﺇ 525 | ﺩ.ﺇ 503 | ﺩ.ﺇ 499 | ﺩ.ﺇ 551 | ﺩ.ﺇ 544 | ﺩ.ﺇ 507 | ﺩ.ﺇ 477 | ﺩ.ﺇ 510 | ﺩ.ﺇ 551 |
| 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
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