
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.

Oceanfront Gem • Pool • High-Floor Sea Views
Discover the best of Fajardo in this oceanfront gem—where each day begins with breathtaking Caribbean sunrises and ends to the soothing sound of waves. Nestled in a peaceful, gated community with a pool and free Wi-Fi, this 1-bedroom retreat offers a queen bed, full bath, and sweeping ocean views. Just minutes from El Yunque, beaches, island ferries, seafood spots, and shops. Whether you're here to relax or explore, your perfect tropical escape starts here—book now and make it unforgettable!

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.

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.

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>

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!

*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.

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

Amazing Infinity pool @Coqui Tropical House

Renald's Place

Fajardo, Las Croabas

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

Casa Tolteca:4BR-Salt Water Pool - Tropical Garden
Condo rentals with a pool

Beautiful oceanfront apartment Ocean Blue Love❤️

Amazing ocean views & close to Bio Bay tours

Ocean View Luxury Condo

Marina's view lll

Villa @ Marina; Near Beach/Easy Access to Islands

Panoramic Ocean View - Sea Charm

Our slice of paradise

Luquillo, Playa Azul Beach Front Apt 20th floor.
Other holiday rentals with a pool

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

The Escape House | Condo in Ceiba

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

Ceiba Retreat #1

Costa Brava

Del Mar y Sol - Vacation Your Way

Harbor & Sky: Marina-Ferry Hub

Spacious 3-Bedroom apartment with ocean view
When is the best time to visit Roosevelt Roads?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $212 AUD | $205 AUD | $205 AUD | $211 AUD | $202 AUD | $201 AUD | $211 AUD | $208 AUD | $194 AUD | $183 AUD | $195 AUD | $211 AUD |
| 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 $56 AUD 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 and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

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