
Holiday rentals with a pool in Culebra
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Culebra

Total holiday rentals
Explore 30 holiday rentals in Culebra

Nightly prices starting at
Culebra holiday rentals start at $90 SGD per night before taxes and fees

Verified guest reviews
Over 5,520 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
30 of Culebra holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Culebra rentals

4.9 Average rating
Culebra stays are highly rated by guests – averaging 4.9 out of 5!
Top-rated rentals with a pool in Culebra
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Cacimar House - Pool, Privacy and Sleeps 6
Welcome to Cacimar House - 10 min to South Shore Beaches and 5 min to Isabel Segunda. Cacimar House offers Pool, Privacy, Location, Quality Furnishings, Attentive House Managers. Perfect for Couples, Families and Friends. 3 bedrooms with two Queens and one King for up to 6 people. 3 bathrooms. Air conditioning in bedrooms. Other rooms include: open kitchen, living room , separate dining room, ping pong room, screened in porch and laundry room. Excellent wi-fi, satellite TV and stereo equipment.

Casa Sunny
NEW immaculately kept saltwater pool. House sleeps 6. Two queen bedrooms and one bedroom with 2 twin bed and one bathroom. Beach amenities. You only need to bring clothes and shoes, a toothbrush and toothpaste (or get that here), we have everything else ready for you! Our TouchStay guest guide includes trip planning support with links to ferry tickets and flight options with a map to all the places you need to know about on the island. Ask us for the perfect 2- or 3-night trip recommendation!

Casa Tesoro-pool home. Walk to beaches/restaurants
Newly renovated home with constant ocean breezes and breathtaking views of the Caribbean Sea and Esperanza Keys. This home offers 'casual luxury' with premium furnishings and cool, comfortable linens and fabrics. We are located in the heart of Esperanza, no car is needed as we are less than a 5 minute walk to the Malecon, Restaurants and 2 minutes to the neighborhood Grocery store. Coco, Esperanza and Sun Bay beaches are a short walk away or enjoy your private pool, one of a few in Esperanza.

Surf Side, Private Salt Water Pool, Ocean View
Across from the turquoise waters of the Atlantic Ocean and a short walk to La Chata Beach, you’ll find Surf Side House, with an expansive ocean view, and the main island of Puerto Rico and the sister island of Culebra as your backdrop. Located in Bravos de Boston on Vieques’ North Shore, this peaceful, private single family home features air conditioned bedroom with king size bed, two bathrooms with showers, one outdoor shower and a private heated salt water pool. Maximum occupancy 2 adults.

Private Pool Bar with Panoramic View! 5* A/C, WiFi
Designed as a private paradise for two adults only, Bonita Vista is centrally located and easy to get to, yet very private. This new hillside retreat features a large covered pool bar with breathtaking views overlooking the Vieques National Wildlife Refuge and the Caribbean Sea. Artifacts from the sugar cane era offer connection to Vieques history. An afternoon poolside slips easily into sunset cocktail hour and dinner from the grill, a swim under the stars or magical moonrise over the bay!

Casa Maya @ Hilltop (private infinity plunge pool)
If you’re craving Caribbean romance, come home to Casa Maya, where the magic of Culebra melds with a touch of passionate India. You’ll gaze out at the blue Bay from the infinity plunge pool, the wrap-around deck, and even inside, from the full kitchen, the king bedroom, and the bathroom. You’ll savor a rainfall shower in a grotto of stones from nearby Flamenco Beach, and candlelit dinners under the Milky Way. “Maya” means “illusion” in Hindi. You’ll pinch yourself to make sure it’s real!

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

Location, Location, Location with Pool
House, 3 Bedroom, 2 full Bathrooms, Sleeps 6 Casa Angie is a newly renovated home across the street from the ocean and a 3-minute walk to the Malecon in the fishing village of Esperanza. The Malecon is a boardwalk fronting the ocean with restaurants, bars and boutique shops, along with water sports rentals. Our Casa with its brand new kitchen is completely equipped for your convenience; whither dining in or barbecuing by the pool, you will surely enjoy your island experience.

Costa Bonita Suite Culebra
Our suite is elegantly decorated in a coastal style, soft tones and comfortable furniture that invite relaxation. The fully equipped kitchen allows you to prepare your favorite meals. The balcony is the perfect place to enjoy outdoor meals with a table for 4 people. It has a king size bed, a queen size sofa bed and a 55'' smart TV. The complex offers a community pool and private dock for dropping off and picking up passengers. All new for you to enjoy an unforgettable stay

Scenic Hideaway Ocean Views & Private Roof Deck
This scenic island hideaway, designed by acclaimed architect John Hix, is a serene oasis perched atop a breezy hill with breathtaking views of the Atlantic Ocean and the Caribbean Sea. The loft features a private rooftop terrace, open-air shower, well-equipped kitchen, high thread count sheets, oversized plush towels, strong WiFi, and a uniquely beautiful shared pool. Despite the privacy of the property, Vieques' best beaches, restaurants, and trail heads are minutes away.

“Casita Agua” @ Campo Alto
***Newly Updated*** Relax and refresh at this unique and tranquil island getaway. Set in the tropical hillside of Mount Resaca, Casita Agua at Campo Alto is the perfect escape while visiting our beautiful island! Spend your days adventuring and your evenings relaxing in the pool. Our casita provides the perfect space for single travelers or couples looking to get away from it all! This studio unit features a dedicated plunge pool, queen bed, kitchenette and custom bath.

Casa Amor Home Esperanza Salt Pool- close to Beach
Casa Amor in Esperanza hills is a dream escape. A case of privacy, offering two fully separate suites, an outdoor dinning area with views of the of the ocean, saltwater pool, and BBQ. Breezes are free! A lovely outdoor shower for a rinse under the stars, a hammock for lazy afternoons… From the pool and gardens, you’ll find ocean views. (Clothing optional) It’s private and peaceful! Tucked into a safe locals’ neighborhood, three blocks from the nearest beach.
Popular amenities for Culebra rentals with a pool
House rentals with a pool

Casa Tolteca:4BR-Salt Water Pool - Tropical Garden

Home for 9 with Pool and Solar Panels in Vieques!

Casa Blanca with pool, tropical garden and rooftop

5Br -3Bth Infinity Pool & Ocean view &Walktobeach

Hilltop Esperanza with ocean views, saltwater pool

Coconut Cay

Breathtaking Oceanfront Vistas by the Reef

Casa Sole Mio!
Apartment rentals with a pool

Cozy Beach Apartment

Serenity Studio ~ Stunning Views / Pool

Costa Bonita Private Villa 604

Beautiful Coast Villa-Culebra

Studio Villa with Pool and Bay View (CB #4101)

Casa Anonna - Hidden oasis & Stunning ocean views

Costa Bonita Private Villa 602
Other holiday rentals with a pool

Esperanza Casita, Pool, Walk to Beach & Top Food

Secluded Villa with Stunning Views & Dipping Pool

Casa Aquabella | Ocean View Villa w/ Private Pool

Villa Mar Azul, Culebra, PR

Quiet 3 bdrms. 3 min to Zoni. Private. 33' pool.

Pool Suite #3 @CBV

Costa Bonita - Suite # 4102

Casa Corona 2026 - Central location with a pool
When is the best time to visit Culebra?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $218 SGD | $245 SGD | $271 SGD | $179 SGD | $179 SGD | $182 SGD | $183 SGD | $182 SGD | $160 SGD | $181 SGD | $172 SGD | $218 SGD |
| Avg. temp | 26°C | 26°C | 26°C | 27°C | 28°C | 29°C | 29°C | 29°C | 29°C | 29°C | 28°C | 27°C |
Destinations to explore
- San Juan Holiday rentals
- Higüey Holiday rentals
- Punta Cana Holiday rentals
- Santo Domingo Este Holiday rentals
- Las Terrenas Holiday rentals
- Fajardo Holiday rentals
- La Romana Holiday rentals
- Ponce Holiday rentals
- Luquillo Holiday rentals
- Aguadilla Holiday rentals
- Sainte-Anne Holiday rentals
- Dominicus Holiday rentals
- Pet-friendly rentals Culebra
- Rentals with a washing machine and dryer Culebra
- House rentals Culebra
- Waterfront rentals Culebra
- Villa rentals Culebra
- Rentals with outdoor seating Culebra
- Rentals with beach access Culebra
- Rentals with a patio Culebra
- Beach house rentals Culebra
- Family-friendly rentals Culebra
- Guest house rentals Culebra
- Beachfront rentals Culebra
- Flat rentals Culebra
- Rentals with pools Culebra
- Rentals with pools Puerto Rico
- Flamenco Beach
- El Yunque National Forest
- Liquillo Beach
- Playa las Picuas, Rio Grande
- Magens Bay Beach
- Coki Beach
- Cane Garden Beach
- Honeymoon Beach
- Secret Harbor Beach
- La Pared Beach
- Cinnamon Bay Beach
- Playa de Luquillo
- Cond Marbella del Caribe Este
- Virgin Islands National Park
- Cane Bay Beach
- Punta Bandera Luquillo PR
- Limetree Beach
- Isla Verde Beach West
- Peter Bay Beach
- Isla Palomino
- Josiah's Bay
- Maho Bay Beach
- Coral World Ocean Park
- Balneario de Luquillo





