
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.

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 * * *

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!

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!

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.

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.

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

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.

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!

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>

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!

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…

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
House rentals with a pool

Amazing Infinity pool @Coqui Tropical House

Local charm, private oasis nearby amenities.

Renald's Place

Fajardo, Las Croabas

Lake and Beach Village, Humacao

Between sea and mountain El Yunque

Renovated Beach House on BEST beach in Puerto Rico

Fabulous Ocean Views /Private Infinity Pool /4 BR
Condo rentals with a pool

Brisa Fresca, Apartment Luquillo PR!

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

Aqua Salada - Window 22, with Ocean/Marina View

Ocean View Luxury Condo

Lovely Ocean View Apartment

*Azul Marino* Golf & Ocean View Luxury Condo

Harry & Maddie’s Beach Getaway

Villa @ Marina; Near Beach/Easy Access to Islands
Other vacation rentals with a pool

Fruit Farm Retreat NEW Pool & Views

Casa Bella, Safe Harbor Marina Next to Ferry Ceiba

Private Island | 1BR Condo | Oceanview | AC | WiFi

Modern 3/2 Apt near Marina Puerto Del Rey & Ferry

River Oasis Retreat

NEW! The Casitas Village

Starfish Ceiba, Entire home with private pool!

Sea Breeze Escape | Sleeps 7 + Pool in Ceiba
When is the best time to visit Roosevelt Roads?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$31,614 GYD | G$30,568 GYD | G$30,568 GYD | G$31,405 GYD | G$30,149 GYD | G$29,940 GYD | G$31,405 GYD | G$30,986 GYD | G$28,893 GYD | G$26,590 GYD | G$26,590 GYD | G$31,405 GYD |
| Avg. temp | 25°C | 25°C | 26°C | 27°C | 28°C | 28°C | 28°C | 29°C | 29°C | 28°C | 27°C | 26°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!
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- Family-friendly rentals Roosevelt Roads
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- House rentals Roosevelt Roads
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- Rentals with pools Ceiba
- Rentals with pools Puerto Rico
- Flamenco Beach
- Honeymoon Beach
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- Magens Bay Beach
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- Distrito T-Mobile
- Playa de Luquillo
- Playa del Dorado
- Coco Beach Golf Club
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- Punta Bandera Luquillo PR
- Playa El Convento
- Hull Bay Beach
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- The Saint Regis Bahia Golf Course




