
Holiday rentals with a pool in Roosevelt Roads
Find and book unique homes with a pool on Airbnb
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 $68 NZD per night before taxes and fees

Verified guest reviews
Over 4,370 verified reviews to help you choose

Family-friendly holiday rentals
90 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 30 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!
Top-rated rentals with a pool in Roosevelt Roads
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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. 45 min to the airport, 50 min to Old San Juan. 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 You must rent a car

Enchanted Pool Beach House
Take it easy at this tropical and peaceful getaway with a private pool where is only for the guest staying at the house. The house is 5 minutes away from many beaches like La Pared Beach, Playa Azul, Costa Azul Beach, Balneario La Monserrate Luquillo and Northeast Ecological Corridor. 10 minutes away from Bioluminescent Bay and Seaven Seas Beach in Fajardo. Also 15 minutes away from El Yunque National Forest in Rio Grande and 5 minutes from Caribbean Cinemas Theater, Shopping mall and Pharmacy.

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.

Beautiful Getaway Home | Private Pool | 4BD
We invite you to stay at our home with a private pool in Hacienda Margarita, ideal for families & groups! - 4 bedroom house with ACs, 2.5 bathrooms, BBQ, 2 SmartTVs, Wi-Fi, etc.! - 24/7 neighborhood security & 5 minutes from Luquillo Beach - Generator & Water tank available - Private pool, yard for soccer & volleyball! - Close to Rainforest, Catamarans, Kayaking, Snorkeling tours & more! - Private Chef and Boat tours available - No loud music, parties, or events - We are Airbnb Superhost!

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.

Wake Up to Ocean Views | Pool + Marina Paradise
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!

Oceanview Penthouse / Private Rooftop • Near Ferry
Private oceanview penthouse on Puerto Rico’s east side, just 8 minutes from the Ceiba ferry to Vieques & Culebra. Enjoy a gated community with on-site security, 2 free parking spaces, and a private rooftop — perfect for relaxing, stargazing, and unwinding after a day exploring the island. Located minutes from beaches, kiosks, El Yunque, and the best of Puerto Rico’s east side.
Popular amenities for Roosevelt Roads rentals with a pool
House rentals with a pool

Amazing Infinity pool @Coqui Tropical House

Casa Blanca with pool, tropical garden and rooftop

5 bedroom Exclusive Beach Villa- WOW!

Fajardo, Las Croabas

Renald's Place

Daddy’s Place Airbnb

Private Dominican-style house on Vieques Beach, Culebra

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

*Azul Marino* Golf & Ocean View Luxury Condo

Waterfront condo w/balcony, pool, minutes to beach

Villa @ Marina; Near Beach/Easy Access to Islands

Ocean Panoramic Views | Walk to Marina & Tours

Two-Story Apartment at Rio Grande Resort

Our slice of paradise

Ocean Plaza Haven | 3BR Stay w/ Views in Luquillo

Beachfront Luxury Apartment w/ Amazing Views
Other holiday rentals with a pool

Vieques ocean view eco villa+pool

Beach Escape 3BR Penthouse Pool, Fast WiFi, Ferry

El Saco Country House

Starfish Ceiba, Entire home with private pool!

Terraza del Sol in Ceiba! Ferry, Puerto del Rey.

Casa Tres Luna

Horizonte Cercano Penthouse/Ferry/Pool/Beach

*NEW Infinity House near El Yunque (private pool)
When is the best time to visit Roosevelt Roads?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $229 NZD | $237 NZD | $237 NZD | $254 NZD | $244 NZD | $242 NZD | $254 NZD | $251 NZD | $234 NZD | $220 NZD | $235 NZD | $254 NZD |
| 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 |
Destinations to explore
- Punta Cana Holiday rentals
- San Juan Holiday rentals
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- Bayahibe Holiday rentals
- La Romana Holiday rentals
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- Culebra Holiday rentals
- Little Saint James Holiday rentals
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- Pet-friendly rentals Roosevelt Roads
- Rentals with a washing machine and dryer Roosevelt Roads
- Rentals with a patio Roosevelt Roads
- Family-friendly rentals Roosevelt Roads
- Condo rentals Roosevelt Roads
- Rentals with outdoor seating Roosevelt Roads
- Fitness-friendly rentals Roosevelt Roads
- Rentals with beach access Roosevelt Roads
- House rentals Roosevelt Roads
- Apartment rentals Roosevelt Roads
- Rentals with pools Ceiba
- Rentals with pools Puerto Rico
- Flamenco Beach
- Isla Verde Beach West
- La Pared Beach
- Rio Mar Village
- Limetree Beach
- Liquillo Beach
- Honeymoon Beach
- Distrito T-Mobile
- Puerto Rico Convention Center
- Magens Bay Beach
- Playa las Picuas, Rio Grande
- Playa de Luquillo
- José Miguel Agrelot Coliseum
- El Yunque National Forest
- Carabali Rainforest Park
- Toro Verde Adventure Park
- Cond Marbella del Caribe Este
- Punta Bandera Luquillo PR
- Plaza Las Americas
- San Patricio Plaza
- Balneario del Escambrón
- Museo de Arte de Puerto Rico
- Sun Bay Beach
- Balneario de Luquillo





