
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.

1BR/E - Walk to Beach/Spectacular Ocean View/Pool
"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 * * *

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.

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.

Oceanview Bay View Penthouse Beach/Marina/Ferry
Enjoy your island escape at Vista Bahía Penthouse in Costa Esmeralda, Ceiba. Relax away from the hustle while staying just 3–5 minutes from the marina, beaches, restaurants, and shopping. The condo features 3 air-conditioned bedrooms and a fully equipped kitchen. Wake up to beautiful sunrises and unwind on the private rooftop with panoramic ocean views. At night, guests love watching the incredible star-filled sky. Perfect for relaxing, stargazing, and enjoying the peaceful island breeze.

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

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-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.

Villa @ Marina; Near Beach/Easy Access to Islands
You'll love our Villa in Fajardo, Puerto Rico. Minutes away from El Yunque Rain Forest, Fajardo and Luquillo Beaches, top restaurants and most importantly, with easy access to Palomino Island, Icacos Island and the world-famous Flamenco Beach located in Culebra Island. The Villa is located in a gated, clean, safe and quiet community, great for couples and families. Villa Marina has great amenities as well! ***Solar panels, Tesla Powerwall Battery, and Water Tank installed***

Private Rainforest Retreat ~10 min to Playa Azul~
Visiting El Yunque & Bio Bay? 🌺 Koko Kai Cabana is the perfect retreat - right between Luquillo and Fajardo - for exploring the Best of the East Coast 🇵🇷... You'll enjoy quiet, country life in the mountains of Juan Martin. But just 15 mins to Luquillo Beach, 20 to El Yunque or Bio Bay & shopping in Fajardo is only 7 mins down the mountain. We live on site, but the cabana is on the "3rd level" above the pool. It's private and tranquil... and everything is just for you two!

Beautiful House, 24/7 Security, Gated Community
Sanitized! Beautiful and comfortable residence with Private Pool, Jacuzzi and Grill. 12min from Palmas del Mar that has beach, bars, night life and sea food restaurant. Minutes from Palma Real Mall, Walmart, restaurants, fast food & much more. 20 min from El Malecon de Naguabo which has many Seafood Restaurants, and beach. 30min to the boat terminal to go to Vieques and Culebra, 40 min from Luquillo Kiosk, 35 min from the Croabas, 45 min to the airport, 50 min to Old San Juan

Huge Salt Pool|Marina Escape|Ocean Views
A tranquil getaway in this stunning apartment with breathtaking ocean views. Step inside to discover modern updates & stylish design. The exclusive 2 suites feature beautiful windows, offering unobstructed view Unwind by the giant pool or enjoy the sunrise from the expansive balcony—perfect spots for relaxation. The fully equipped kitchen with exotic white granite countertops is ideal for whipping up meals. This is the perfect retreat for those seeking luxury & serenity!
Popular amenities for Roosevelt Roads rentals with a pool
House rentals with a pool

Amazing Infinity pool @Coqui Tropical House

Casona Mirimou-Country and Beach House!

Renald's Place

Fajardo, Las Croabas

Daddy’s Place Airbnb

Casa Domirriqueña privada playa Vieques, Culebra

Hacienda Azucena, Río Grande, Yunque Rain Forest

❤️PRIVATE POOL,Beach home,BioBay Tour walk distance
Apartment rentals with a pool

Beautiful oceanfront apartment Ocean Blue Love❤️

Aqua Salada Window 27, with Ocean/Marina View

Blue Pearl-1 Beachfront Retreat @ Playa La Pared

Ocean View Luxury Condo

*Azul Marino* Golf & Ocean View Luxury Condo

Aqua Blue- Breathtaking Oceanview at Las Croabas

Panoramic Ocean View - Sea Charm

Our slice of paradise
Other holiday rentals with a pool

Fruit Farm Retreat NEW Pool & Views

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

River Oasis Retreat

Costa Bella Rooftop Ceiba, PR

Starfish Ceiba, Entire home with private pool!

Stylish Escape Private Pool near Ferry and Beach

Ceiba Retreat #2

Del Mar y Sol - Vacation Your Way
When is the best time to visit Roosevelt Roads?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £113 | £110 | £110 | £113 | £108 | £107 | £113 | £111 | £104 | £98 | £104 | £113 |
| 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 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 £30 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
90 of Roosevelt Roads holiday rentals include wifi 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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- Rentals with pools Puerto Rico
- Flamenco Beach
- Honeymoon Beach
- Limetree Beach
- Liquillo Beach
- Distrito T-Mobile
- Magens Bay Beach
- Playa las Picuas, Rio Grande
- Playa de Luquillo
- Rio Mar Village
- Carabali Rainforest Park
- Toro Verde Adventure Park
- La Pared Beach
- Punta Bandera Luquillo PR
- Isla Verde Beach West
- Museo de Arte de Puerto Rico
- José Miguel Agrelot Coliseum
- Plaza Las Americas
- Balneario del Escambrón
- San Patricio Plaza
- Sun Bay Beach
- Las Paylas
- Cond Marina Lanais
- Balneario de Luquillo
- Playita del Condado




