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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.

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Top guest favorite
Apartment in Vieques
4.98 out of 5 average rating, 132 reviews

1BR/W - Spectacular Ocean View/Pool/Walk to Beach

"Villa del Sol" is a delightful, modern villa with our 2BR apartment upstairs and two spacious 1BR apartments below. Perched up high with panoramic views of the ocean, it is just a 5-minute walk from two secluded beaches. Fully gated, it has a paved drive and parking, and an in-ground pool. This charming 1BR apartment has high quality furniture and furnishings, a fully equipped kitchen, a large bedroom, flatscreen TV, WIFI & AC. * * * CLICK ON "Show More" BELOW TO CONTINUE THE DESCRIPTION * * *

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, 197 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!

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
4.99 out of 5 average rating, 288 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 favorite
A private swimming pool is nestled against a backdrop of the ocean and marina, providing panoramic views. Four people are seated at the pool's edge, enjoying the refreshing water. Lush palm trees sway gently in the breeze, enhancing the tranquil setting.
Apartment in Fajardo
4.94 out of 5 average rating, 142 reviews

Vistamar- Stunning Caribbean views & private pool!

Open, spacious and breezy with full length balcony overlooking Puerto del Rey marina and the islands. Relax, swim in our private pool and take in the beautiful Caribbean views. Short drive to east coast beaches, El Yunque Rain Forest, discounts on boat trips to Icacos and Culebra. Located in a quiet gated neighborhood, the entire 2nd floor of a private home, with private entrances, and easy parking. Full kitchen, BBQ, and washer/dryer make for a comfortable stay. Longterm rental available.

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, 172 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.

Top guest favorite
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, 198 reviews

Casa Encanto - Experience El Yunque Rainforest.

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 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, 122 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 favorite
The image captures a tranquil coastal scene featuring a marina filled with boats moored along a dock. Lush green hills rise in the background, with a cluster of buildings nestled atop. The clear blue waters reflect the sky, creating a serene atmosphere.
Condo in Fajardo
4.83 out of 5 average rating, 131 reviews

Oceanfront Relaxation | High-Floor w/ Views & Pool

Wake up to stunning Caribbean sunrises and fall asleep to the gentle sound of ocean waves at this oceanfront escape in Fajardo. Located in a quiet, gated community with a pool and free Wi-Fi, this 1-bedroom condo features a queen bed, sofa bed, full bathroom, and panoramic ocean views. You're just minutes from El Yunque, island ferries, fresh seafood, and local shops. Whether you’re seeking adventure or pure relaxation, your perfect getaway starts here—book now and experience paradise!

Guest favorite
Condo in Fajardo
4.96 out of 5 average rating, 112 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>

Top guest favorite
A wooden cabin is set within a lush landscape, featuring open double doors that reveal a cozy seating area. Comfortable benches are positioned on a wooden deck, surrounded by greenery. A pathway made of stepping stones leads towards the entrance, enhancing accessibility.
Place to stay in Río Grande
4.98 out of 5 average rating, 263 reviews

Glamping at Relaxing Atmosphere In Nature

Glamping at Relaxing Atmosphere In Nature (RAIN) provides a serene and private getaway where you can relish the magic of the rainforest, with the calming sounds of rain, birds, and the Coqui's call. Our latest cabin is outfitted with all the comforts to ensure your glamping experience is unforgettable. Comfortably immerse yourself in the forest's flora and fauna. Escape the bustle of modern life and unwind. We embrace and celebrate diversity; all are welcome!

Guest favorite
A refreshing swimming pool features a cascading water feature along a stone wall. Nearby, a shaded dining area is visible under a red umbrella, accompanied by a set of four outdoor chairs and a rectangular table.
Home in Ceiba
4.9 out of 5 average rating, 105 reviews

Casa Génesis

Spend quality time with your family in a relaxing space. The accommodation allows you to enjoy a hot day in a refreshing pool. Its location gives you the opportunity to explore the beauty of the island's east. Near the residence are various attractions and among these you can find the Las Tinajas River, El Hippie River, Seven Seas Spa, Los Machos Beach, Ceiba Ferry Terminal, Puerto del Rey Marina, Las Croabas…

Top guest favorite
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, 102 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?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$31,614 GYDG$30,568 GYDG$30,568 GYDG$31,405 GYDG$30,149 GYDG$29,940 GYDG$31,405 GYDG$30,986 GYDG$28,893 GYDG$26,590 GYDG$26,590 GYDG$31,405 GYD
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 G$8,375 GYD per night before taxes and fees

  • Verified guest reviews

    Over 4,290 verified reviews to help you choose

  • Family-friendly vacation rentals

    80 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!