
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 $77 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.

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.

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

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.

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

Casa Suiza-Private Couple Escape with Heated Pool
Casa Suiza is a romantic getaway retreat, only for couples with a heated pool. We are located in the mountains. It is very private, away from the city, an hour away from San Juan and Puerto Rico International Airport. We recommend renting an SUV or 4x4 vehicle for your peace of mind, if you are not used to traveling in the mountains. Once you start climbing the mountain, it is along winding streets and some steep slopes, but completely passable.

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

Enchanted Pool Beach House

Hacienda Azucena, Río Grande, Yunque Rainforest

Fabulous Ocean Views /Private Infinity Pool /4 BR

El Saco Country House

Casa Tesoro-pool home. Walk to beaches/restaurants

Renald's Place

Casa Amor Home Esperanza Salt Pool- close to Beach

Beautiful Rooftop Getaway | Jacuzzi by Rainforest
Apartment rentals with a pool

Ocean Front Resort Villa

Oceanview Penthouse / Private Rooftop • Near Ferry

Beachfront Luxury Apartment w/ Amazing Views

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

Ocean View Luxury Condo

Our slice of paradise

Villa @ Marina; Near Beach/Easy Access to Islands

Ocean View Apt + Balcony | Next to El Conquistador
Other holiday rentals with a pool

Private Rainforest Retreat ~10 min to Playa Azul~

Wake Up to Ocean Views | Pool + Marina Paradise

Luxury Villa 5340

Tierra Linda TreeHouse Private Pool & River

Apartment with Ocean View near Ceiba FerryTerminal

*NEW Infinity House near El Yunque (private pool)

Starfish Ceiba, Entire home with private pool!

Almendro Signature Suite @ El Yunque Luxury Retreat
When is the best time to visit Roosevelt Roads?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $174 SGD | $181 SGD | $181 SGD | $194 SGD | $186 SGD | $185 SGD | $194 SGD | $191 SGD | $178 SGD | $168 SGD | $180 SGD | $194 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
- House rentals Roosevelt Roads
- 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
- 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
- Puerto Rico Convention Center
- Magens Bay Beach
- Rio Mar Village
- Honeymoon Beach
- José Miguel Agrelot Coliseum
- La Pared Beach
- Playa de Luquillo
- Carabali Rainforest Park
- Cond Marbella del Caribe Este
- Toro Verde Adventure Park
- 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
- Hacienda Campo Rico





