Some info has been automatically translated. Show original language

Vacation 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.

%{current} / %{total}1 / 1
Top guest favorite
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, 166 reviews

Casa Suiza - Couple Retreat with Heated Pool

Casa Suiza es un lugar para escapadas románticas, sólo para parejas con Piscina Climatizada. Estamos 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. En su beneficio, una vez comience a subir a la montaña, es por calles con curvas y algunas pendientes empinadas, pero completamente transitables. Recomendamos rentar un vehículo SUV o 4x4 para su tranquilidad, si no está acostumbrado a transitar en la Montaña.

Superhost
Condo in Fajardo
4.86 out of 5 average rating, 119 reviews

Oceanfront Gem • Pool • High-Floor Sea Views

Discover the best of Fajardo in this oceanfront gem—where each day begins with breathtaking Caribbean sunrises and ends to the soothing sound of waves. Nestled in a peaceful, gated community with a pool and free Wi-Fi, this 1-bedroom retreat offers a queen bed, full bath, and sweeping ocean views. Just minutes from El Yunque, beaches, island ferries, seafood spots, and shops. Whether you're here to relax or explore, your perfect tropical escape starts here—book now and make it unforgettable!

Guest favorite
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, 201 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 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
4.98 out of 5 average rating, 300 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 favorite
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, 176 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 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
4.98 out of 5 average rating, 129 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.

Guest favorite
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 favorite
A serene pool area is surrounded by manicured landscaping and swaying palm trees. Lounge chairs are positioned near the water, and a tall structure provides a backdrop with distinct architectural features. The clear blue water reflects the bright sky, creating a tranquil atmosphere.
Apartment in Fajardo
4.89 out of 5 average rating, 141 reviews

Casita Jardín- Cozy 1 Bedroom Apt with Pool

Beautiful Garden View apartment located in a luxurious colorful village. Come enjoy this amazing apartment equipped with all the amenities you need for a fun, relaxing and romantic getaway. De-stress in our village’s pool and hot tub facilities just steps from the villa. Unwind with a good book on our balcony chaise lounge chairs or disconnect into nature in round of golf in El Conquistador’s beautiful golf course amenities. You will never want to leave. *No Pets Allowed*

Guest favorite
Condo in Ceiba
4.85 out of 5 average rating, 198 reviews

The East Point P.R. Ceiba-Fajardo-Bio Bay- Yunque

Welcome to Puerto Rico eastern side. Our cozy shack is located near Seven Seas Beach (like 12min.), Rooselvet Roads Naval Base (15 min.), Vieques and Culebras Island Ferry Port (we can help you purchase tickets in advance and transportation) Luquillo, s Kioskos and Beach, El Yunque and Zipline (20 minutos) and Old San Juan (50min.) Our apartment is within a complex composed of 3 pools, half a basketball court, jungle gym and is a gate community with adequate security.

Guest favorite
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, 163 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 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
4.93 out of 5 average rating, 101 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.

Popular amenities for Roosevelt Roads rentals with a pool

When is the best time to visit Roosevelt Roads?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ555ﺩ.ﺇ536ﺩ.ﺇ536ﺩ.ﺇ551ﺩ.ﺇ529ﺩ.ﺇ525ﺩ.ﺇ551ﺩ.ﺇ544ﺩ.ﺇ507ﺩ.ﺇ477ﺩ.ﺇ510ﺩ.ﺇ551
Avg. temp25°C25°C26°C27°C28°C28°C28°C29°C29°C28°C27°C26°C

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.ﺇ147 per night before taxes and fees

  • Verified guest reviews

    Over 3,980 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!