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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.

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Guest favourite
A comfortable lounge area is furnished with two reclining chairs facing a large flat-screen television, mounted on a dark wall. Shelving units feature subtle decor items, while soft lighting enhances the space's ambiance. Potted plants add a touch of greenery to the setting.
Home in Ceiba
4.93 out of 5 average rating, 125 reviews

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.

Guest favourite
Home in Luquillo
4.92 out of 5 average rating, 221 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.

Top Guest favourite
A wooden terrace is shown with a stool positioned near the railing. The sun rises above a distant landscape, casting warm light over lush green hills and the ocean. An infinity pool is visible nearby, blending beautifully with the scenic surroundings.
Tiny home in Fajardo
4.98 out of 5 average rating, 345 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!

Top Guest favourite
An aerial view of a spacious house is displayed, featuring a well-maintained swimming pool enclosed by a privacy fence. A covered bar area with seating is included, alongside several lounge chairs positioned near the pool. Lush greenery and a cloudy sky complete the serene setting.
Cottage in Naguabo
4.97 out of 5 average rating, 145 reviews

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

Top Guest favourite
A contemporary house is positioned atop a hill, surrounded by lush greenery and palm trees. A winding pathway leads to the entrance, while panoramic ocean views extend in the background, highlighting the beauty of the surrounding landscape.
Home in Ceiba
4.98 out of 5 average rating, 158 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.

Top Guest favourite
A covered porch features two woven chairs and a small table, with a stunning sunset visible over the horizon. The pool and landscaped yard can be seen in the foreground, framed by lush greenery.
Home in Ceiba
4.95 out of 5 average rating, 101 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).

Top Guest favourite
A modern villa with expansive balconies overlooks a serene infinity pool. Lounge chairs are arranged along the poolside, surrounded by lush greenery and palm trees. The clear blue sky complements the contemporary design of the structure.
Home in Vieques
4.96 out of 5 average rating, 102 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

Top Guest favourite
Tiny home in Luquillo
4.96 out of 5 average rating, 123 reviews

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!

Guest favourite
Home in Humacao
4.92 out of 5 average rating, 313 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.

Top Guest favourite
A tranquil outdoor pool is seen, featuring a sunbathing area with two sleek lounge chairs. The pool's clear water reflects the bright blue sky with fluffy clouds, while tropical plants enhance the scenic mountainous backdrop.
Tiny home
4.99 out of 5 average rating, 198 reviews

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.

Superhost
An inviting infinity pool extends toward a breathtaking view of lush green mountains and the Atlantic Ocean. The sky is filled with fluffy white clouds, creating a serene atmosphere. The pool's clear blue water reflects the vibrant landscape, offering a perfect retreat for relaxation.
Cabin in Gurabo
4.86 out of 5 average rating, 384 reviews

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.

Top Guest favourite
Guest suite in Luquillo
5.0 out of 5 average rating, 224 reviews

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

When is the best time to visit Roosevelt Roads?

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