
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 €53 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.
ValueFamilyAmenities
4.93 out of 5 average rating, 128 reviews
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.
LocationFamilyBathroom
4.93 out of 5 average rating, 230 reviews
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!
ValueFamilyCleanliness
4.96 out of 5 average rating, 156 reviews
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!
FamilyValueCheck-in
4.98 out of 5 average rating, 358 reviews
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.
ValueFamilyBreakfast
4.98 out of 5 average rating, 162 reviews
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.
FamilyLocationLaundry
4.89 out of 5 average rating, 235 reviews
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).
LocationFamilyHeating
4.95 out of 5 average rating, 103 reviews
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
FamilyLocationOutdoor spaces
4.96 out of 5 average rating, 103 reviews
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.
ValueFamilyBack garden
4.92 out of 5 average rating, 317 reviews
Ocean View Luxury Condo
My wife and I took great time to remodel our apt considering that we were sold on the High floor ocean view, the moonlight view at night, overlooking the marina, and beautiful mountains overlapping the ocean.Our balcony, off course, is our favorite location, where we hear the sound of the waves, the boats in and out of the marina,the manaties on the water, and the breathtaking winds on both sides of your apt.The apt is very romantic and family oriented at the same time.
FamilyValueSleep quality
4.96 out of 5 average rating, 274 reviews
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. Beachfront house. A unique concept with a swim-up bar connected to the terrace for guests' greater enjoyment. Three fully equipped bedrooms, next to the Paseo El Malecón and 12 minutes from Walmart and all the international stores. Close to everything.We always have drinking water on our property. To enter, there is a lockbox with the keys.
FamilyLocationGetting around
4.97 out of 5 average rating, 153 reviews
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.
LocationFamilyNearby
4.9 out of 5 average rating, 354 reviewsPopular amenities for Roosevelt Roads rentals with a pool
House rentals with a pool

Hacienda Azucena, Río Grande, Yunque Rainforest
LocationValueKitchen
4.95 out of 5 average rating, 197 reviews
Private pool, nearby beach, Wi-Fi, pet-friendly
FamilyLocationHospitality
4.93 out of 5 average rating, 102 reviews
Amazing Infinity pool @Coqui Tropical House
LocationValueComfort
4.98 out of 5 average rating, 127 reviews
Beautiful Rooftop Getaway | Jacuzzi by Rainforest
ValueFamilyWifi
4.93 out of 5 average rating, 151 reviews
5 bedroom Exclusive Beach Villa- WOW!
ValueFamilyNearby
4.95 out of 5 average rating, 152 reviews
Pool +near beaches, amazing home/Back up Water
ValueLocationGetting around
4.98 out of 5 average rating, 136 reviews
Casa Tesoro-pool home. Walk to beaches/restaurants
LocationFamilyGetting around
4.99 out of 5 average rating, 164 reviews
Fajardo, Las Croabas
ValueLocationGetting around
4.88 out of 5 average rating, 145 reviewsApartment rentals with a pool

Oceanview Penthouse / Private Rooftop • Near Ferry
LocationFamilyParking
4.93 out of 5 average rating, 115 reviews
Ocean Front Resort Villa
ValueLocationView
4.89 out of 5 average rating, 135 reviews
Pristine 4 bdrm (all private) steps to beach/golf
LocationFamilyAmenities
4.95 out of 5 average rating, 103 reviews
Beachfront Luxury Apartment w/ Amazing Views
LocationValueKitchen
4.96 out of 5 average rating, 199 reviews
Our slice of paradise
FamilyLocationOutdoor spaces
4.94 out of 5 average rating, 402 reviews
Private Rooftop|Ferry&Marina|Airport| Power Backup
LocationFamilyKitchen
4.97 out of 5 average rating, 244 reviews
Beachfront Apt. Ocean-Facing Bed & City Views+Pool
LocationFamilyKitchen
4.89 out of 5 average rating, 445 reviews
Stunning Ocean and Marina view spacious Penthouse
ValueFamilyKitchen
4.98 out of 5 average rating, 101 reviewsOther holiday rentals with a pool

Family House with Pool on the Naguabo esplanade
ValueLocationNearby
4.93 out of 5 average rating, 329 reviews
Casa Suiza-Private Couple Escape with Heated Pool
ValueLocationComfort
4.99 out of 5 average rating, 205 reviews
Romantic Chalet with Pool by the River
LocationFamilyPool
4.96 out of 5 average rating, 104 reviews
BEAUTIFUL HOUSE WITH A PRIVATE POOL IN EL YUNQUE
LocationFamilyAccuracy
4.95 out of 5 average rating, 150 reviews
Hacienda Torres Paradise of Nature - Villa Limon
LocationValueParks
4.88 out of 5 average rating, 188 reviews
Vistamar- Stunning Ocean views & private pool!
ValueFamilyCheckout
4.94 out of 5 average rating, 157 reviews
Private Rainforest Retreat ~10 min to Playa Azul~
ValueFamilyDecor
4.96 out of 5 average rating, 130 reviews
Wake Up to Ocean Views | Pool + Marina Paradise
LocationFamilyPool
4.93 out of 5 average rating, 151 reviewsWhen is the best time to visit Roosevelt Roads?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €119 | €123 | €123 | €126 | €120 | €120 | €132 | €130 | €121 | €114 | €122 | €132 |
| 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
- Carolina Holiday rentals
- Las Terrenas Holiday rentals
- Punta Cana Holiday rentals
- Santo Domingo Este Holiday rentals
- Santo Domingo Holiday rentals
- Fajardo Holiday rentals
- Culebra Holiday rentals
- La Romana Holiday rentals
- Ponce Holiday rentals
- Luquillo Holiday rentals
- Flamenco Beach
- El Yunque National Forest
- Liquillo Beach
- Playa las Picuas, Rio Grande
- Puerto Rico Convention Center
- Rio Mar Village
- Distrito T-Mobile
- Magens Bay Beach
- José Miguel Agrelot Coliseum
- La Pared Beach
- Cond Marbella del Caribe Este
- Playa de Luquillo
- Honeymoon Beach
- Plaza Las Americas
- Punta Bandera Luquillo PR
- Limetree Beach
- San Patricio Plaza
- Isla Verde Beach West
- Hacienda Campo Rico
- Cond Ashford Imperial
- Isla Palomino
- Museo de Arte de Puerto Rico
- Balneario de Luquillo
- Cond Marina Lanais





