
Vacation rentals with a pool in Roosevelt Roads
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Top-rated rentals with a pool in Roosevelt Roads
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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.

Private Rooftop|Ferry&Marina|Airport| Power Backup
This amazing 2-story Penthouse offers breathtaking views of Culebra and Vieques Islands. With 3 bedrooms, 2 bathrooms, a rooftop terrace, and the exclusive distinction of being the only property in the community with a reliable power backup system, it provides all the comforts and conveniences you need. Located near Marina Puerto del Rey, Ceiba Airport, and the Ceiba Ferry Terminal; it definitely offers easy access to a variety of exciting activities. Create unforgettable family memories!

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.

Casa Suiza (Mountainous Area)
Casa Suiza es un lugar para escapadas románticas, sólo para parejas. Estamos ubicados en lo alto de la montaña, es muy privado y alejado de la ciudad, a una hora de distancia de San Juan y el Aeropuerto Internacional de Puerto Rico. Tenga en cuenta que dirigirse a nuestra propiedad es por calles con curvas y algunas pendientes empinadas, pero completamente transitables. Recomendamos rentar un vehículo SUV o un 4x4 para su tranquilidad, si no está acostumbrado a transitar en la Montaña.

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.

Hacienda Torres Paradise of Nature - Villa Limon
2 bedroom, 1 bathroom apartment in the middle of a 40 acre private property with peaceful ambiance. We have very friendly farm dogs that are loose and will interact with guests. You will be serenated by birds during the day and coquis at night! 5 min access to highway #53. Near beaches, marinas, restaurants, ferry to Culebra and Vieques islands and Roosevelt Roads Airport.

High Marina Ocean View - The Black Circle
Welcome to your own private bohemian paradise in Fajardo, Puerto Rico! This stunning studio apartment is the perfect blend of japandi-bohemian style and luxurious comfort, located on the 18th floor of a prestigious building with a marina and breathtaking ocean views.

Casa La Piña Puerto Rico!
Come visit La Pina in Puerto Rico, stay at Hampton homes premium to enjoy all your tropical adventures. We are close to beaches, restaurants, rainforest and ferry's that lead to the islands of Culebra and Viequez.
Popular amenities for Roosevelt Roads rentals with a pool
House rentals with a pool

Amazing Infinity pool @Coqui Tropical House

Beautiful Getaway Home | Private Pool | 4BD

HIDDEN PARADISE, SPECTACULAR OCEAN VIEW, GETAWAY!

Renald's Place

Lake and Beach Village, Humacao

Domirriqueña House

El Yunque Paradise - Private pool

Renovated Beach House on BEST beach in Puerto Rico
Condo rentals with a pool

Gorgeous Ocean views studio, beachfront property!

Aqua Salada Window 22, with Ocean/Marina View

Ocean View Luxury Condo

Lovely Ocean View Apartment

*Azul Marino* Golf & Ocean View Luxury Condo

The ReFresh | Warm minimalist seaviewing retreat

Waterfront High-Rise Apt with Gorgeous Ocean View

Marina’s ll ocean view apartment
Other vacation rentals with a pool

Ocean and Land View - Tiny House on an acre with an ocean view

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

Costa Esmeralda #1, Ceiba PR

Casita Jardín- Cozy 1 Bedroom Apt with Pool

Esperanza 2 BR Apt, Pool, Walk to Beach & Top Food

Sea Breeze Escape | Sleeps 7 + Pool in Ceiba

Remodeled! Gated Home Near Ocean!

Fajardo-Ceiba Harmony Beach Apartment @ CostaBrava
Quick stats about vacation rentals with a pool in Roosevelt Roads
Total rentals
90 properties
Nightly prices starting at
R696 ZAR before taxes and fees
Total number of reviews
4.3K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
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