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Vacation rentals with a pool in Roosevelt Roads

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Roosevelt Roads

  • Total vacation rentals

    Explore 90 vacation rentals in Roosevelt Roads

  • Nightly prices starting at

    Roosevelt Roads vacation rentals start at ﺩ.ﺇ 220 per night before taxes and fees

  • Verified guest reviews

    Over 4,330 verified reviews to help you choose

  • Family-friendly vacation rentals

    90 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Roosevelt Roads vacation 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 favorite
Home in Luquillo

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.

FamilyValueCheckout

4.93 out of 5 average rating, 230 reviews
Top guest favorite
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

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!

LocationValueQuiet

4.96 out of 5 average rating, 156 reviews
Top guest favorite
Cottage in Naguabo

Casa Familiar con Piscina en malecón de Naguabo

Disfruta de un alojamiento privado y completamente cercado, ideal para compartir con familia y amigos con total comodidad y seguridad. 🚗 A solo 30 segundos del Malecón, con una gran variedad de los mejores restaurantes 🏖️ A 2 minutos de la playa Fanduca 🎯 Amenidades: 🏊 Piscina privada 🎱 Billar 🤸 Trampolín 🧸 Columpio 🚗 Estacionamiento 📶 WiFi 🏀 Baloncesto 🏐 Volleyball Diversión garantizada. Ven a crear momentos inolvidables con tu familia en nuestra hermosa isla de Puerto Rico 🇵🇷

FamilyValueTV

4.93 out of 5 average rating, 329 reviews
Top guest favorite
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

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!

FamilyValueBeach

4.98 out of 5 average rating, 357 reviews
Top guest favorite
A modern living area features a black leather sofa, a circular coffee table, and a woven area rug. Natural light floods the space through large glass doors, leading to a balcony. A TV and workspace are also visible, complementing the contemporary design.
Condo in Machos

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.

LocationFamilyWalkability

4.93 out of 5 average rating, 115 reviews
Top guest favorite
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

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.

FamilyLocationCleanliness

4.98 out of 5 average rating, 162 reviews
Top guest favorite
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

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).

ValueLocationBackyard

4.95 out of 5 average rating, 103 reviews
Top guest favorite
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

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

FamilyLocationBreakfast

4.96 out of 5 average rating, 103 reviews
Guest favorite
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

Casa Escape Cerca del ferry(Vieques y culebra)

En CASA ESCAPE estarás cerca de todo. Encontrarás en el centro del pueblo varios negocios entre ellos restaurantes, panaderías, farmacias, banco y otras. Estarás a 8 min del Terminal del ferry Vieques y Culebra, 3 min de Playa Medio mundo , 3min de Marina Puerto del Rey, 15 min de Villa Marina, 20 min de las Croabas y playa Seven Sea, donde encontrar diversidad de restaurantes y actividades recreativas, 15 min de los kiosco y playa de Luquillo y 25 min del Yunque National Forestal.

LocationValueBackyard

4.93 out of 5 average rating, 128 reviews
Top guest favorite
Home in Humacao

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.

FamilyValueHospitality

4.92 out of 5 average rating, 317 reviews
Top guest favorite
Cottage in Naguabo

Casa Playa Tropical, Terraza y Piscina Unidas

Ven y disfruta con toda la familia en esta espaciosa casa, TROPICAL BEACH HOUSE - CASA PLAYA TROPICAL. Casa frente a la playa, Único concepto con piscina bar unida a la terraza para un mejor deleite para los huespedes. Tres habitaciones totalmente equipadas, al lado del Paseo El Malecon y a 12 minutes de Walmart y today las tiendas internacionales, Cerca de Todo., Siempre tenemos agua potable en nuestra propiedad, Para entral hay una cajita de seguridad con las llave.,

FamilyLocationOutdoor spaces

4.97 out of 5 average rating, 153 reviews
Top guest favorite
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

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.

ValueFamilyAmenities

4.9 out of 5 average rating, 353 reviews

Popular amenities for Roosevelt Roads rentals with a pool

Other vacation rentals with a pool

When is the best time to visit Roosevelt Roads?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 496ﺩ.ﺇ 514ﺩ.ﺇ 514ﺩ.ﺇ 525ﺩ.ﺇ 503ﺩ.ﺇ 499ﺩ.ﺇ 551ﺩ.ﺇ 544ﺩ.ﺇ 507ﺩ.ﺇ 477ﺩ.ﺇ 510ﺩ.ﺇ 551
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