
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 €52 per night before taxes and fees

Verified guest reviews
Over 4,330 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!
Top-rated rentals with a pool in Roosevelt Roads
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Casa Escape Close to the ferry (Vieques and Culebra)
At CASA ESCAPE you'll be close to everything. You will find several businesses in the center of town, including restaurants, bakeries, pharmacies, a bank and others. You will be 8 minutes from the Vieques and Culebra Ferry Terminal, 3 minutes from Playa Medio Mundo, 3 minutes from Marina Puerto del Rey, 15 minutes from Villa Marina Villa, 20 minutes from Las Croabas and Seven Sea Beach, where you will find a variety of restaurants and recreational activities, 15 minutes from the kiosks and Luquillo Beach and 25 minutes from the Yunque National Forest.

Casa Playa Tropical, with an open-plan terrace and pool
Come and enjoy the whole family in this spacious home, TROPICAL BEACH HOUSE - TROPICAL BEACH HOUSE. House in front of the beach, Only concept with pool bar attached to the terrace for a better delight to the guests. Three fully equipped rooms, one with a king size bed and its own private bathroom, another with a double bed, a bunk bed and another bathroom, and another with another double bed and another bunk bed. We always have drinking water on our property. There is a security box and key to get in.

Mountain-to-Ocean Views • Private Luxury Retreat
Luxury Villa | Private Pool, Views & Prime Location 💧Water Reserve ⚡ Generator Escape to paradise in this elegant 4BR / 2.5BA villa in a gated community, just minutes from El Yunque Rainforest, beaches, Bio Bay, waterfalls, catamaran tours, ATV & dining 🏝️ Private pool & sun deck with mountain-to-ocean views ⚡Fast Wi-Fi & A/C 🍹 BBQ & dining lounge SUV & Private Chef available upon request (additional fee applies) Where tropical luxury, privacy, and unforgettable experiences come together

Fabulous Ocean Views /Private Infinity Pool /4 BR
Relax at this spacious home with a private heated infinity pool with swim-up bar! With fabulous ocean and rainforest views from two covered decks, this house is family-friendly in a safe gated community only 5 minutes from Luquillo Beach and 15 minutes from the Rainforest. Other nearby activities include world-class golf, bio-bay kayaking, jet skis, ATV, horseback riding, go-karts, snorkeling, scuba diving, ziplining, great restaurants & a casino. Community pool, basketball & tennis courts too!

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.

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 Mami y Papi including private suite
Bring your family and friends to this gated home wih beautiful views of the islands and Caribeen Sea. Minutes from beautiful beaches like Seven Seas (7 miles), and El Yunque Rainforest (8.8 miles), surfing at La Pared (9.4 miles), Boat trips from Puerto Del Rey (2 miles). For nightlife and shopping the Luquillo Kiosks offer 60 open air businesses with food, drinks (7.8 miles). The famous Laguna Grande Bio Bay in Fajardo is just (7.6 miles) away. Ferries to Vieques and Culebra (3 miles).

Vieques ocean view eco villa+pool
-Privately nestled on three acres with Caribbean Sea views from the second floor. -Three private bedroom suites - mosquito nets. Villa doesn’t have Ac -Spa and yoga classes nearby at Finca Victoria -Full service amenities can be arranged: stocking the fridge, chef, massages. -Gunite swimming pool - solar powered -Each bedroom has its own bathroom, dressing area & outdoor shower -The beds are fitted with quality 400-count cotton linens - Strict no children under the age of 10years policy

Entire property in Fajardo 5 minutes from ferry
Your East Tropical Escape in Fajardo, Bella!!, Two story house on a corner, private, nice patio with pool, 5 minutes to Vieques and Culebra's ferry. Close to the Bio Bay in Las Croabas, 3 minutes from grocery stores, pharmacies and restaurants. Gated community with security, common areas with a nice pool, tennis, volley ball and basket ball courts, close to beautiful beaches, kayaking, 20 minutes from the Rain Forest (El Yunque), a must see! 1 minute from Marina Puerto Del Rey.

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.

Family House with Pool on the Naguabo esplanade
Enjoy a private, fully fenced-in accommodation, ideal for sharing with family and friends in complete comfort and safety. 🚗 Just a 30-second walk from Malecón (esplanade), which has a great variety of top restaurants 🏖️ 2 minutes from Fanduca Beach 🎯 Amenities: 🏊 Private pool 🎱 Billiard 🤸 Trampoline 🧸 Swing 🚗 Parking 📶 WiFi 🏀 Basketball 🏐 Volleyball Fun guaranteed. Come and create unforgettable moments with your family on our beautiful island of Puerto Rico 🇵🇷

ONE STOP VACATION HOME, w private pool and jaquzzi
ONE STOP VACATION HOMES OFFERS PRIVATE POOL W/ JACUZZI If you are looking for a place where you can relax at the private pool and entertain with family or a few friends at a beautiful place, !your search ends here!. This great property which is located just a few minutes from Seven Sea Beach, Las Croabas, Biobay, Scuba diving, El Yunque Rain Forest, Zipline at the Rain Forest, ATV Riding at Carabali, Luquillo Kioskos and Luquillo Beach.
Popular amenities for Roosevelt Roads rentals with a pool
House rentals with a pool

Hacienda Azucena, Río Grande, Yunque Rainforest

Amazing Infinity pool @Coqui Tropical House

5 bedroom Exclusive Beach Villa- WOW!

Fajardo, Las Croabas

Casita Paraíso

Renald's Place

Casa Tesoro-pool home. Walk to beaches/restaurants

Beautiful Getaway Home | Private Pool | 4BD
Apartment rentals with a pool

Ocean View Luxury Condo

Beachfront Luxury Apartment w/ Amazing Views

Oceanview Penthouse / Private Rooftop • Near Ferry

Oceanview Bay View Penthouse Beach/Marina/Ferry

New! Breath Taking View at Las Casitas Village

Pristine 4 bdrm (all private) steps to beach/golf

Private Rooftop|Ferry&Marina|Airport| Power Backup

The Felix:Family friendly-pool-3minWalk2Beach-8ppl
Other holiday rentals with a pool

Ocean Bliss Oceanfront view apartment

Beachfront Luxury @ Wyndham Rio Mar Resort

BEAUTIFUL HOUSE WITH A PRIVATE POOL IN EL YUNQUE

Hacienda Torres Paradise of Nature - Villa Limon

Vistamar- Stunning Ocean views & private pool!

Starfish Ceiba, Entire home with private pool!

Rustic Retreat- El Yunque view, pool and game room

Tropical Bliss * 10 min to Ferry~Pool~Beach~BBQ
When is the best time to visit Roosevelt Roads?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €116 | €121 | €121 | €123 | €118 | €117 | €129 | €128 | €119 | €112 | €120 | €129 |
| 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
- San Juan Holiday rentals
- Higüey Holiday rentals
- Punta Cana Holiday rentals
- Santo Domingo Este Holiday rentals
- Las Terrenas Holiday rentals
- Santo Domingo Holiday rentals
- Fajardo Holiday rentals
- La Romana Holiday rentals
- Ponce Holiday rentals
- Luquillo Holiday rentals
- Aguadilla Holiday rentals
- Dominicus Holiday rentals
- Flamenco Beach
- El Yunque National Forest
- Liquillo Beach
- Playa las Picuas, Rio Grande
- Puerto Rico Convention Center
- Distrito T-Mobile
- Rio Mar Village
- Magens Bay Beach
- La Pared Beach
- José Miguel Agrelot Coliseum
- Cond Marbella del Caribe Este
- Playa de Luquillo
- Honeymoon Beach
- Punta Bandera Luquillo PR
- Plaza Las Americas
- Limetree Beach
- San Patricio Plaza
- Isla Verde Beach West
- Isla Palomino
- Museo de Arte de Puerto Rico
- Balneario de Luquillo
- Cond Ashford Imperial
- Hacienda Campo Rico
- Cond Marina Lanais





