
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 $85 AUD 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 and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
90 of Roosevelt Roads holiday 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.

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.

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!

Casa Playa Tropical, Tropical Beach House & Pool
Come and enjoy with the whole family in this spacious house, TROPICAL BEACH HOUSE - CASA PLAYA TROPICAL. Beachfront house, unique concept with pool bar attached to the terrace for a better delight to guests. Three fully equipped rooms, one with a king size bed and its private bathroom, another with a double bed, a bunk bed and another bathroom and another with another double bed and another bunk bed. We have an automatic 40 kilo electric generator, for entry there is a safety box with key

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 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).

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

Private Rainforest Retreat ~10 min to Playa Azul~
Visiting El Yunque & Bio Bay? 🌺 Koko Kai Cabana is the perfect retreat - right between Luquillo and Fajardo - for exploring the Best of the East Coast 🇵🇷... You'll enjoy quiet, country life in the mountains of Juan Martin. But just 15 mins to Luquillo Beach, 20 to El Yunque or Bio Bay & shopping in Fajardo is only 7 mins down the mountain. We live on site, but the cabana is on the "3rd level" above the pool. It's private and tranquil... and everything is just for you two!

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.

Casa Suiza-Private Couple Escape with Heated Pool
Casa Suiza is a romantic getaway retreat, couples only with Climate Pool. We are located in the mountain, it is very private, away from the city, an hour away from San Juan and the Aeropuerto Internacional de Puerto Rico. We recommend washing an SUV or 4x4 vehicle for your peace of mind, if you are not used to riding in the Mountain. Once you start climbing the mountain, it's through curved streets and some steep, but completely walkable slopes.

The Best View of PR with infinity pool with Heater
Campo Cielo is the perfect place to disconnect and be in complete connection with nature. You will enjoy the most beautiful sunrise from the mountains of the El Yunque National Forest. You'll relax and recharge with pure, fresh air, while enjoying the best view in the infinity pool and on the terrace. The best experience to enjoy nature and feel just one step away from heaven, you will find it in our hidden treasure, Campo Cielo Mountain Retreat.

Casa Encanto Rainforest Retreat
Nestled in the lush foothills of El Yunque Rainforest, this private guest suite occupies the lower level of our luxury villa, Casa Encanto. Enjoy the perfect blend of tranquility and adventure, just minutes from Luquillo Beach, Las Paylas, Carabalí Adventure Park, snorkeling, and more. Relax by the pool and spa while enjoying the peace of a tropical retreat powered by solar energy, Tesla battery backup, and a dedicated water reserve.
Popular amenities for Roosevelt Roads rentals with a pool
House rentals with a pool

Beautiful Getaway Home | Private Pool | 4BD

Fabulous Ocean Views /Private Infinity Pool /4 BR

Hacienda Azucena, Río Grande, Yunque Rainforest

Hilltop Cabin w/ Pool & Views – 18 Mins to Airport

Ana's place

Hacienda Margarita-Infinity Pool, Lg Home & Views!

ONE STOP VACATION HOME, w private pool and jaquzzi

Intimate retreat with a hot tub and private pool
Condo rentals with a pool

Beachfront Luxury Apartment w/ Amazing Views

Ocean Front Resort Villa

Oceanview Penthouse / Private Rooftop • Near Ferry

Ocean View Luxury Condo

Our slice of paradise

Fajardo PR Modern Oceanfront Condo Million $ Views

Private Rooftop|Ferry&Marina|Airport| Power Backup

Beachfront Apt. Ocean-Facing Bed & City Views+Pool
Other holiday rentals with a pool

Villa Vista Hermosa, Río Grande, Puerto Rico

Tierra Linda TreeHouse Private Pool & River

Wake Up to Ocean Views | Pool + Marina Paradise

Starfish Ceiba, Entire home with private pool!

*NEW Infinity House near El Yunque (private pool)

Apartment with Ocean View near Ceiba FerryTerminal

Casa Tres Luna

Tropical Bliss * 10 min to Ferry~Pool~Beach~BBQ
When is the best time to visit Roosevelt Roads?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $191 AUD | $198 AUD | $198 AUD | $202 AUD | $194 AUD | $192 AUD | $212 AUD | $209 AUD | $195 AUD | $184 AUD | $197 AUD | $212 AUD |
| 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
- Distrito T-Mobile
- Magens Bay Beach
- José Miguel Agrelot Coliseum
- Honeymoon Beach
- La Pared Beach
- Playa de Luquillo
- Cond Marbella del Caribe Este
- Puerto Rico Convention Center
- Punta Bandera Luquillo PR
- Plaza Las Americas
- Limetree Beach
- San Patricio Plaza
- Isla Verde Beach West
- Museo de Arte de Puerto Rico
- Isla Palomino
- Balneario de Luquillo
- Rio Mar Village
- Cond Ashford Imperial
- Plaza Del Mercado De Santurce
- Cond Marina Lanais





