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Holiday rentals with a pool in Roosevelt Roads

Find and book unique homes with a pool on Airbnb

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 vibrant sunrise casts warm hues over the ocean, framed by lush green palm fronds. The view extends over the coastal landscape, showcasing buildings and distant hills against the expansive horizon.
Condo in Machos
4.9 out of 5 average rating, 203 reviews

Oceanview Bay View Penthouse Beach/Marina/Ferry

Enjoy your island escape at "Vista Bahía Penthouse" in Costa Esmeralda. There is something special about Ceiba – sleeping away from the hustle and bustle of everyday life and only minutes away from multiple activities and places you will enjoy. 3 to 5 minutes to marina, beaches, restaurants, shopping, and more. Wake up to sunrises right outside your window. The condo features 3 bedrooms air-conditioned, kitchen with all the convenience. Relax on the private rooftop with ocean panoramic views!

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, 303 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!

Guest favourite
A serene balcony setting is depicted, featuring a small dining table with two chairs. The table is set with plates and a pitcher, overlooking a scenic view of palm trees and a tranquil sea. The horizon stretches out toward distant islands under a clear blue sky.
Apartment in Cabezas
4.96 out of 5 average rating, 178 reviews

Luxury Ocean Front Studio

Luxurious beachfront apartment to spend a beautiful day. It is located next to the Hotel El Conquistador with an incredible view. With a view to the sea, you can see Palomino Island, Icaco Cay, Island Culebra and Vieques. This apartment is unique, romantic and elegant to have a good time. It has different attractions nearby such as the Yunque, Seven Seas Beach,Snorkel and beach tours, Ferry to Culebra and Vieques. Different areas for night activities such as the Bio Bay in the Croabas.

Superhost
A serene pool area is framed by tropical palm trees, with a gazebo featuring string lights in the foreground. The pool reflects the evening sky, while lush greenery surrounds the space, providing a sense of tranquility and natural beauty.
Apartment in Ceiba
4.84 out of 5 average rating, 177 reviews

Mountainside Ocean View Pool/Family Fun 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.

Top Guest favourite
A serene outdoor area features a sparkling pool surrounded by lush greenery and tropical plants. A shaded seating area is provided by a large umbrella, along with a cozy hanging chair in the background. The peaceful ambiance is enhanced by bright blue skies.
Guest suite in Luquillo
5 out of 5 average rating, 207 reviews

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

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 in Naguabo
4.99 out of 5 average rating, 169 reviews

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.

Guest favourite
Condo in Fajardo
4.94 out of 5 average rating, 118 reviews

Oceanfront Oasis: Panoramic Views & Marina Access

Charming studio with breathtaking views, located in Fajardo on the stunning east coast of Puerto Rico, just 45 minutes from San Juan. This is the perfect romantic escape from the everyday routine, ideal for up to Two Guests. If your group exceeds two, we invite you to explore our second property with two bedrooms. Enjoy pristine beaches, top tourist attractions, and fantastic dining options nearby. Plus, you're just 20 minutes from the ferry to Culebra or Vieques islands!<br><br>

Guest favourite
A private balcony offers stunning ocean views, with outdoor seating arranged around a circular table. A palm tree is partially visible, and the horizon showcases gentle waves under a clear sky.
Condo in Fajardo
4.89 out of 5 average rating, 164 reviews

*Azul Marino* Golf & Ocean View Luxury Condo

Azul Marino is our spacious one bedroom overlooking the east coast of Puerto Rico. Located inside a 5 stars resort, you have a golf course, 2 pools, hot tubs and be near the main excursions of Puerto Rico. Be minutes away from the bioluminescent bay, take a catamaran to the islands and enjoy a entire day at the beach doing snorkeling or just relaxing. This apartment had a full size kitchen, enormous living room and a very confortable king size in the bedroom.

Top Guest favourite
The master bedroom features a spacious king bed with luxury linens, complemented by a light-colored comforter. Large sliding doors lead to the pool deck, while vaulted wooden ceilings enhance the room's open feel. A modern fan and bedside lamps provide additional comfort.
Cottage in Vieques
4.99 out of 5 average rating, 250 reviews

Casa Corona - Amazing Views, Pool, Close to Beach

Experience this newly renovated home with constant ocean breezes and breathtaking views of the Corona Reef, Culebra and the "Big Island." This cozy cottage offers 'casual luxury' with premium furnishings and cool, comfortable linens and fabrics. Enjoy the ocean-facing plunge pool and outdoor shower. Located just past the former W Resort on a private fenced/gated lot that's minutes from everything (airport, ferry, restaurants, beaches and shopping).

Guest favourite
A cozy seating area features a blue hanging chair and a small gray stool. Large glass doors provide access to a balcony with stunning views of the water. Light-colored tiled flooring and partially opened windows enhance natural light in the space.
Condo in Fajardo
4.93 out of 5 average rating, 376 reviews

Waterfront condo w/balcony, pool, minutes to beach

Welcome to your private oceanfront escape in Fajardo, Puerto Rico. This one-bedroom apartment is offers panoramic views, pool and beach gear, and the comforts of home. Ideal for couples or small groups seeking comfort, connection through the senses, and Caribbean charm. The location in the northeastern corner of PR provides excellent ocean sounds, natural lighting, marine life sightings, and trade winds.

Top Guest favourite
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
4.93 out of 5 average rating, 102 reviews

Ocean View Rooftop Condo Vista Azul Penthouse

Beautiful Ocean View Penthouse Apartment located in the East Side Coast of Ceiba Puerto Rico. The apartment is in a closed gated community with on site Security. There are 2 parking spaces available. Only 7 minutes away from the Ferry Terminal to Vieques and Culebra, 5 minutes away from playa Macho, about 20 minutes from Luquillo Kiosk and 30 minutes from the National Rainforest in Rio Grande.

Top Guest favourite
A modern studio apartment features a comfortable gray sofa adorned with striped pillows. A large wall-mounted TV provides entertainment options. Glass sliding doors offer a view of the ocean, while a semi-private sleeping area with a queen bed is visible in the background.
Apartment in Fajardo
4.98 out of 5 average rating, 111 reviews

Oceanfront, new remodeled studio

Escape to a spectacular new remodeled, recently renovated and fully equipped oceanfront studio. A place to relax, retreat, reset and enjoy a beautiful experience. Located in the northeast coast of Fajardo, Puerto Rico and close to beautiful beaches, water activities, restaurants and touristic places.

Popular amenities for Roosevelt Roads rentals with a pool

When is the best time to visit Roosevelt Roads?

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Avg. price$253 NZD$244 NZD$244 NZD$251 NZD$241 NZD$239 NZD$251 NZD$248 NZD$231 NZD$217 NZD$233 NZD$251 NZD
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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 $67 NZD per night before taxes and fees

  • Verified guest reviews

    Over 3,980 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!