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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 $76 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.

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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, 128 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.

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Top guest favourite
Cottage in Naguabo
4.97 out of 5 average rating, 151 reviews

Playa Tropical House, Terrace and Pool Together

Come and enjoy the whole family in this spacious home, TROPICAL BEACH HOUSE - TROPICAL BEACH HOUSE. House in front of the beach, Only concept with pool bar attached to the terrace for a better delight to the guests. Three fully equipped rooms, one with a king size bed and its own private bathroom, another with a double bed, a bunk bed and another bathroom, and another with another double bed and another bunk bed. We always have drinking water on our property. There is a safety box with a key for the entrance.

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Top guest favourite
An infinity pool with illuminated edges provides a serene atmosphere during twilight. A swim-up bar is positioned at one side, while lounge chairs are visible nearby. A basketball hoop is set up next to the pool, and surrounding tropical foliage completes the tranquil outdoor space.
Home in Luquillo
4.96 out of 5 average rating, 155 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!

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Guest favourite
Home in Luquillo
4.93 out of 5 average rating, 228 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.

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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, 356 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!

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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, 161 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.

ValueLocationBack garden

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, 102 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).

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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, 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

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Top guest favourite
Home in Humacao
4.92 out of 5 average rating, 317 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.

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Top guest favourite
Cottage in Naguabo
4.93 out of 5 average rating, 328 reviews

Family House with Pool on the Naguabo esplanade

Enjoy a private, fully fenced-in accommodation, ideal for sharing with family and friends in complete comfort and safety. 🚗 Just a 30-second walk from Malecón (esplanade), which has a great variety of top restaurants 🏖️ 2 minutes from Fanduca Beach 🎯 Amenities: 🏊 Private pool 🎱 Billiard 🤸 Trampoline 🧸 Swing 🚗 Parking 📶 WiFi 🏀 Basketball 🏐 Volleyball Fun guaranteed. Come and create unforgettable moments with your family on our beautiful island of Puerto Rico 🇵🇷

ValueLocationDecor

Top guest favourite
A bright living area features large glass doors that open to a balcony overlooking the marina. Colorful artwork adorns the walls, and a light-colored sofa provides a comfortable seating option. The room benefits from natural light, creating a welcoming ambiance.
Apartment in Fajardo
4.96 out of 5 average rating, 273 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.

ValueFamilyWalkability

Top guest favourite
A two-story vacation home features a light-colored exterior with decorative balconies. The entrance is marked by a central door flanked by two smaller doors. Lush greenery surrounds the property, enhancing the welcoming appearance. A paved pathway leads to the home, with a well-maintained lawn visible.
Home in Fajardo
4.9 out of 5 average rating, 352 reviews

ONE STOP VACATION HOME, w private pool and jaquzzi

ONE STOP VACATION HOMES OFFERS PRIVATE POOL W/ JACUZZI If you are looking for a place where you can relax at the private pool and entertain with family or a few friends at a beautiful place, !your search ends here!. This great property which is located just a few minutes from Seven Sea Beach, Las Croabas, Biobay, Scuba diving, El Yunque Rain Forest, Zipline at the Rain Forest, ATV Riding at Carabali, Luquillo Kioskos and Luquillo Beach.

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Popular amenities for Roosevelt Roads rentals with a pool

When is the best time to visit Roosevelt Roads?

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Avg. price$171 SGD$177 SGD$177 SGD$181 SGD$174 SGD$172 SGD$190 SGD$187 SGD$175 SGD$165 SGD$176 SGD$190 SGD
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