
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 $51 SGD per night before taxes and fees

Verified guest reviews
Over 4,370 verified reviews to help you choose

Family-friendly holiday rentals
90 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 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.

Vistamar- Stunning Ocean views & private pool!
Experience an open, spacious, and breezy retreat with a full-length balcony overlooking Puerto del Rey Marina and the Caribbean islands. Relax by the private pool and enjoy stunning ocean views in a tranquil setting. Minutes from east coast beaches, El Yunque National Forest, and boat trips to Icacos & Culebra. Private 2nd-floor apartment with separate entrance, gated parking, full kitchen, BBQ, washer/dryer, workspace, and everything needed for a comfortable island stay. Long-term stays welcome

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 You must rent a car

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!

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.

Mountainside Ocean View & Pool Treasure Hunt Ferry
Experience Puerto Rico's rainforest at our mountaintop apartment. Coqui's and owls create a natural background at night. 1 full apartment including garage parking. Full kitchen, full bedroom, living room converts to a queen bed. 18' pool with ocean view 12' gazebo. 3 acres of trails to hike, trampoline, and zip line for children. kayak and beach equipment. transportation to ferry available. Our boat is also available seek a water adventure. very kid friendly - must be ok with dogs.

Casa Encanto Rainforest Retreat
This Guest Suite, on the lower level of our exclusive luxury villa, Casa Encanto, is the perfect tropical getaway. Nestled in the peaceful and lush foothills of the El Yunque Rain Forest, Located in Luquillo with many nearby attractions. You’ll have easy access to downtown Luquillo, El Yunque National Rainforest, Luquillo Beach, Caribali Adventure Park, Las Paylas, charter boat trips, snorkeling, zip lines and much more. The Guest Suite is fully solar with Tesla Batteries and backup water

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 Suiza-Private Couple Escape with Heated Pool
Casa Suiza es un retiro de escapadas románticas, sólo para parejas con Piscina Climatizada. Estamos ubicados en la montaña, es muy privado, alejado de la ciudad, a una hora de distancia de San Juan y el Aeropuerto Internacional de Puerto Rico. Recomendamos rentar un vehículo SUV o 4x4 para su tranquilidad, si no está acostumbrado a transitar en la Montaña. Una vez comienzas a subir a la montaña, es por calles con curvas y algunas pendientes empinadas, pero completamente transitables.

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!

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

Ana's place
Tu familia estará cerca de todo hospedándote en este alojamiento céntrico. Estamos ubicados a 10 minutos de los kioskos de luquillo, cerca del yunque, a 20 minutos de la hacienda carabali , cerca de diferentes playas como Seven seas y las croabas, cerca del puerto para ir a las islas municipio Vieque y culebra. El alojamiento cuenta con diferentes amenidades como por ejemplo billar, barbecue y piscina.
Popular amenities for Roosevelt Roads rentals with a pool
House rentals with a pool

Amazing Infinity pool @Coqui Tropical House

Home for 9 with Pool and Solar Panels in Vieques!

Fajardo, Las Croabas

Renald's Place

Daddy’s Place Airbnb

Casa Domirriqueña privada playa Vieques, Culebra

Entre mer et montagne El Yunque

Hacienda Azucena, Río Grande, Yunque Rain Forest
Apartment rentals with a pool

Oceanfront Gem • Pool • High-Floor Sea Views

Oceanview VistaBahía Penthouse Beach/Marina/Ferry

Aqua Salada - Window 22, with Ocean/Marina View

Ocean View Luxury Condo

Marina’s ll ocean view apartment

Villa @ Marina; Near Beach/Easy Access to Islands

Our slice of paradise

Beachfront Luxury Apartment w/ Amazing Views
Other holiday rentals with a pool

Beach Escape 3BR Penthouse Pool, Fast WiFi, Ferry

Villa Florece - Conecta con la Naturaleza

Ceiba Retreat #1 A minutos del Ferry

Starfish Ceiba, Entire home with private pool!

Friends & Family Getaway Villa- Pickle-ball Court

Casa Larimar with Pool & Solar System near Beach

Stylish Escape Private Pool near Ferry and Beach

Villa Respira
When is the best time to visit Roosevelt Roads?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $173 SGD | $179 SGD | $179 SGD | $192 SGD | $184 SGD | $183 SGD | $192 SGD | $189 SGD | $177 SGD | $166 SGD | $178 SGD | $192 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
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- Family-friendly rentals Roosevelt Roads
- Rentals with beach access Roosevelt Roads
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- Pet-friendly rentals Roosevelt Roads
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- Rentals with pools Ceiba
- Rentals with pools Puerto Rico
- Flamenco Beach
- Isla Verde Beach West
- Limetree Beach
- Liquillo Beach
- Puerto Rico Convention Center
- Distrito T-Mobile
- Magens Bay Beach
- Playa las Picuas, Rio Grande
- Honeymoon Beach
- José Miguel Agrelot Coliseum
- El Yunque National Forest
- Rio Mar Village
- Playa de Luquillo
- La Pared Beach
- Toro Verde Adventure Park
- Carabali Rainforest Park
- Cond Marbella del Caribe Este
- Punta Bandera Luquillo PR
- Plaza Las Americas
- San Patricio Plaza
- Sun Bay Beach
- Museo de Arte de Puerto Rico
- Balneario de Luquillo
- Hacienda Campo Rico





