
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.

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!

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.

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.

Fajardo PR Modern Oceanfront Condo Million $ Views
Case del Encanto is a beautiful oceanfront condo that offers quiet comfort, modern amenities, and unrivaled panoramic views of the Atlantic Ocean, El Yunque, and the islands of Icacos, Palominos, Culebra & Vieques. Make this oasis your destination for rainbows, manatees and turtles, soothing tropical breezes, and glorious sunrises/sunsets. Our goal is to create a tropical getaway for sophisticated adults living their best lives enjoying the beauty, nature, and culture of Puerto Rico.

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!

*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.

Our slice of paradise
Spacious studio apartment, located on the 22nd floor with stunning views of the East Coast Icacos and Palomino Islands. Unit has cooktop, microwave, and full size refrigerator. Kitchen is also equipped with utensils, crockery and cutlery. The complex has a laundry area on ground floor with washer and dryer for a small fee. It also has a swimming pool, tennis court, basket ball court and 24/7 security. It’s the perfect place to enjoy the breeze and relax.

Oceanfront | Newly Remodeled | Stunning Views
Stunning oceanfront studio by El Conquistador—perfect for a honeymoon, anniversary, or quiet escape. Sip coffee on your private balcony with Palomino in view. Elegant finishes, queen bed, spacious bath. Cook in a real kitchen (stove, full-size fridge, microwave); coffee pods included. Fast Wi-Fi + Roku tv. Pool access. Beach chairs/towels provided. Close to El Yunque, the Bioluminescent Bay, and ferries to Culebra/Vieques.

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.

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

Renald's Place

Fajardo, Las Croabas

Beautiful House, 24/7 Security, Gated Community

Lake and Beach Village, Humacao

Surf Side, Private Salt Water Pool, Ocean View

Renovated Beach House on BEST beach in Puerto Rico

Fabulous Ocean Views /Private Infinity Pool /4 BR

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

Ocean Front Lovely 1-bedroom condo with pool

Oceanfront Gem • Pool • High-Floor Sea Views

Amazing ocean views & close to Bio Bay tours

🌟Delightful Panoramic View at Marina's Getaway I 🌟

Ocean View Luxury Condo

Marina's view lll

Waterfront condo w/balcony, pool, minutes to beach

Lovely 2-2 Condo with the best view of Puerto Rico
Other holiday rentals with a pool

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

El Saco Country House

Costa Bella Rooftop Ceiba, PR

Del Mar y Sol - Vacation Your Way

Private Penthouse Paradise

Pent House | Ocean Views | Ferry Vieques-Culebra

Horizonte Near Penthouse/Ferry/Pool/Beach

Fajardo-Ceiba Harmony Beach Apartment @ CostaBrava
When is the best time to visit Roosevelt Roads?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $193 SGD | $186 SGD | $186 SGD | $192 SGD | $184 SGD | $183 SGD | $192 SGD | $189 SGD | $176 SGD | $166 SGD | $178 SGD | $192 SGD |
| 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 $51 SGD 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 Ceiba
- Rentals with pools Puerto Rico
- Flamenco Beach
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