
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 €52 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 Escape Close to the ferry (Vieques and Culebra)
At CASA ESCAPE you'll be close to everything. You will find several businesses in the center of town, including restaurants, bakeries, pharmacies, a bank and others. You will be 8 minutes from the Vieques and Culebra Ferry Terminal, 3 minutes from Playa Medio Mundo, 3 minutes from Marina Puerto del Rey, 15 minutes from Villa Marina Villa, 20 minutes from Las Croabas and Seven Sea Beach, where you will find a variety of restaurants and recreational activities, 15 minutes from the kiosks and Luquillo Beach and 25 minutes from the Yunque National Forest.
4.93 out of 5 average rating, 128 reviews
Pristine 4 bdrm (all private) steps to beach/golf
Indulge in a breathtaking getaway nestled in the plush private golf/spa resort, Hyatt Regency Grand Reserve. The only resort in PR to host the Puerto Rico Open. This exquisite 4-bedroom (all bedrooms are private), 3 1/2 bath villa boasts scenic views of the lush El Yunque rainforest, a turquoise sea, 2 Tom Kite golf courses & a private pool. Gated, resort-style villas in Rio Grande, just 25 minutes from the SJU airport, 10 minutes from the El Yunque rain forest, and 35 minutes from San Juan.
4.95 out of 5 average rating, 103 reviews
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.
4.93 out of 5 average rating, 229 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!
4.96 out of 5 average rating, 155 reviews
5 bedroom Exclusive Beach Villa- WOW!
Discover Puerto Rico at a safe, beachfront, gated community in a nature preserve in the town of Humacao. Experience local life of fresh food in small family-run eateries and quiet beaches in our large five-bedroom beach villa with two outdoor spa showers, grill and a NEW POOL. In a private beach just at the end of our street, and private entrance to the nature preserve for great hiking and nature viewing for birds, fish, crabs, and other island animals. Prolific Turtle nesting zone. Book Now!
4.95 out of 5 average rating, 152 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!
4.98 out of 5 average rating, 357 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.
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).
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
4.96 out of 5 average rating, 103 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.
4.92 out of 5 average rating, 317 reviews
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.
4.96 out of 5 average rating, 273 reviews
Casa Playa Tropical, with an open-plan terrace and pool
Come and enjoy the whole family in this spacious home, TROPICAL BEACH HOUSE - TROPICAL BEACH HOUSE. Beachfront house. A unique concept with a swim-up bar connected to the terrace for guests' greater enjoyment. Three fully equipped bedrooms, next to the Paseo El Malecón and 12 minutes from Walmart and all the international stores. Close to everything.We always have drinking water on our property. To enter, there is a lockbox with the keys.
4.97 out of 5 average rating, 152 reviewsPopular amenities for Roosevelt Roads rentals with a pool
House rentals with a pool

Ocean View Sunset
4.87 out of 5 average rating, 127 reviews
Private pool, nearby beach, Wi-Fi, pet-friendly
4.93 out of 5 average rating, 101 reviews
Hacienda Azucena, Río Grande, Yunque Rainforest
4.95 out of 5 average rating, 197 reviews
Renald's Place
4.92 out of 5 average rating, 181 reviews
Casita Paraíso
4.96 out of 5 average rating, 267 reviews
Fajardo, Las Croabas
4.88 out of 5 average rating, 144 reviews
Beautiful Getaway Home | Private Pool | 4BD
4.93 out of 5 average rating, 172 reviews
Casa Tesoro-pool home. Walk to beaches/restaurants
4.99 out of 5 average rating, 163 reviewsApartment rentals with a pool

Beachfront Luxury Apartment w/ Amazing Views
4.96 out of 5 average rating, 199 reviews
Las Casitas, Panoramic Ocean View – Fajardo, PR
4.9 out of 5 average rating, 180 reviews
Private Rooftop|Ferry&Marina|Airport| Power Backup
4.97 out of 5 average rating, 244 reviews
Oceanview Bay View Penthouse Beach/Marina/Ferry
4.89 out of 5 average rating, 235 reviews
Oceanview Penthouse / Private Rooftop • Near Ferry
4.93 out of 5 average rating, 115 reviews
Fajardo PR Modern Oceanfront Condo Million $ Views
4.97 out of 5 average rating, 145 reviews
Beachfront Apt. Ocean-Facing Bed & City Views+Pool
4.89 out of 5 average rating, 444 reviews
Oceanfront Paradise • Pool • Relax & Unwind
4.89 out of 5 average rating, 275 reviewsOther holiday rentals with a pool

BEAUTIFUL HOUSE WITH A PRIVATE POOL IN EL YUNQUE
4.95 out of 5 average rating, 149 reviews
Private Rainforest Retreat ~10 min to Playa Azul~
4.96 out of 5 average rating, 129 reviews
Mountain-to-Ocean Views • Private Luxury Retreat
4.98 out of 5 average rating, 123 reviews
Family House with Pool on the Naguabo esplanade
4.93 out of 5 average rating, 329 reviews
Hacienda Torres Paradise of Nature - Villa Limon
4.88 out of 5 average rating, 187 reviews
Ocean Bliss Oceanfront view apartment
4.92 out of 5 average rating, 316 reviews
Vistamar- Stunning Ocean views & private pool!
4.94 out of 5 average rating, 157 reviews
Villa Vista Hermosa, Río Grande, Puerto Rico
4.97 out of 5 average rating, 142 reviewsWhen is the best time to visit Roosevelt Roads?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €118 | €122 | €122 | €125 | €119 | €118 | €131 | €129 | €120 | €113 | €121 | €131 |
| 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
- José Miguel Agrelot Coliseum
- La Pared Beach
- Cond Marbella del Caribe Este
- Playa de Luquillo
- Honeymoon Beach
- Plaza Las Americas
- Punta Bandera Luquillo PR
- San Patricio Plaza
- Limetree Beach
- Isla Verde Beach West
- Isla Palomino
- Museo de Arte de Puerto Rico
- Hacienda Campo Rico
- Balneario de Luquillo
- Cond Ashford Imperial
- Cond Marina Lanais





