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Holiday rentals with a pool in Road Town

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Road Town

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Top guest favourite
An outdoor area features a private pool surrounded by a deck with lounge chairs. Lush greenery and rocky landscaping create a natural setting, while the two-story house offers large glass windows that showcase scenic views of the hillside.
Villa in Wesley Will
5.0 out of 5 average rating, 68 reviews

Villa Naku, escape and relax.

Villa Naku is a perfect Tortola getaway, enjoy the neighborhood beach Rogues Bay or a quick drive to the the many other spots on Tortola. Situated on one of the most incredible spots on a point, facing east to capture the prevailing and often strong sea breezes, wake up to the majestic sunrise views from practically any room in the villa. The open plan kitchen, living and dining room are in the heart of the house, other areas to enjoy include an outdoor BBQ with lounge, pool and an upper sitting area with a fireplace, hammock and loungers, games and TV room, the whole house is equipped with Air Conditioning two bedrooms with private balconies and all bedrooms with king beds with quality mattresses. There is a Sonos system that can be controlled from your phone. The movie room below with a 65” TV and hidden 50” TV in the upper casual seating area. The house also has two Apple TVs, allowing you to sign in to your personal account or Naku’s. Naku recently completed was designed and is owned by one of the BVI’s local Architects striving to make the home as energy efficient as possible. Partnering with local craftsmen and Artisans most of the villa was constructed by hand. The friendly neighborhood of Rogues Point is unique, each property on the point is not less than an acre providing ample privacy. Albeit close to essential amenity, yet often feels as though you are the only ones on the serene point, perfect for those looking for inspiration and seclusion. The terrain is best explored with a 4WD vehicle, we have attached a list of rental agencies. Each room has a special, unique vibe, two of the three are en suite, the Master with two decks, has an exceptionally large bathroom with separate toilet room and laundry shoot, The second master bedroom below has a private deck and a shower with an outstanding view. The third bedroom has an incredible view with access directly to the pool deck. Whether you wish to cook or hire a chef Naku is equipped with Blue Star gas range & Napoleon grill for your use. The kitchen has a 60” Refrigerator freezer, appliances along with a Breville Barista Espresso machine.. Just off the upper seating area is a pergola space with a central fire pit surrounded by Adirondack chairs, overlooking is our gigantic Buda along with the other Bali sculptures, just up the garden is our King sized hammock for the afternoon siestas or just starring at the stars. Behind the upper seating area is the sheltered lounge and BBQ patio all surrounded by terraced gardens. The lower terraces are accessed through the movie room to the pool, the entire house was designed around monumental boulders, the pool is tucked in amongst them with a wind protected sun lounging area just beyond. There is a fully equipped laundry room for your use, we offer cleaning service’s two times a week, but we can organize more if required. The house is prepped and ready for your adventures with beach chairs, beach towels, and coolers. If you are traveling with small children, we can assist with a trundle bed or crib, car seat and other toys. Please let us know if you require any of these items ahead of time so we can have them prepared.

Guest favourite
An open and airy kitchen features white cabinetry complemented by colorful accents. A large island with bar stools invites gathering. Natural light floods the space through a window, illuminating shelves filled with tableware. A coastal chandelier hangs gracefully from the vaulted ceiling.
Villa in Coral Bay
4.89 out of 5 average rating, 109 reviews

Periwinkle Cottage in Coral Bay w/Pool, and Views🏝

Periwinkle Cottage of Coral Bay is a perfect rendition of a traditional West Indian cottage with modern amenities. 🌴 Ceiling fans, large screened in porch and open air porch areas. Located at the end of a private road, Periwinkle has a Million Dollar view of Coral Bay! Located only minutes from grocery stores, shopping & dining in Coral Bay. This cottage offers privacy & sits on over a half acre lot! You are right near the Virgin Islands National Park and some of the best beaches in the world

Top guest favourite
An outdoor patio features tiled stones surrounding a small salt-system plunge pool. Two lounge chairs with cushions are positioned nearby, while lush green banana plants fill the background. A beige umbrella provides shade, and the sky is bright with scattered clouds.
Cottage in Coral Bay
4.99 out of 5 average rating, 156 reviews

Sweet Spice: A Nifty Little Cottage. With A Pool!

This very small 1 BR cottage lives BIG with a screened porch, SOLAR POWER, valley views, ac, dishwasher, outdoor fitness, and plunge pool. With a clean modern vibe, Sweet Spice is more laidback getaway than luxury villa. It’s an ideal HQ for 2 active STJ adventurers - but with a few extra amenities! Located off the beaten path on the quiet side of STJ, it feels secluded but is only a 5 minute drive to the shops of Coral Bay. Note: road is rough and requires a 4WD and there are LOTS of stairs.

Top guest favourite
A shaded patio area features a long seating arrangement with blue cushions and decorative pillows, paired with a blue lounge chair that includes a yellow accent pillow. Nearby, a small round table in a deep blue color complements the surroundings.
Villa in Ballast Bay
4.93 out of 5 average rating, 87 reviews

Villa Almondeen- Peaceful 2bedroom villa with pool

Villa Almondeen sits about 100 feet from the water’s edge in a private and secured area. It is five minutes away from the popular Cane Garden Bay Beach and 15 minutes from other close-by beaches. You can enjoy views of Jost Van Dyke and the boating activities around the “Bay.” To the left is an area called “The Pointe,” a line-fishing and snorkeling area, and to the right is the famous “Smith’s Toe (pronounced “Smittoe”), another fishing area, and home to the blue parrot fish.

Top guest favourite
Apartment in Cruz Bay
4.92 out of 5 average rating, 146 reviews

Rockroom One Bedroom Condo at The Hills Saint John

"The Rockroom" is a one bedroom apartment located within The Hills Saint John. This large space with amazing views of Cruz Bay and St Thomas features a large bedroom with King bed, two full baths, a large living area and a full kitchen. There is also a large private patio with a gas grill and patio furniture. Guests staying at Rockroom will also have access to The Clubhouse Bar (open seasonally and located on the property) as well as a 24 hour fitness center and community pool.

Guest favourite
Villa in Road Town
4.83 out of 5 average rating, 29 reviews

Lloyd Hill Villas Holiday Suite

Welcome to your new sanctuary! This fully furnished two-bedroom, two-bath suite is located at the Lloyd Hill Villas and offers the ideal blend of sea breeze and sun, and quiet comfortable living. With the added luxury of a swimming pool and a view of nearby Guana Island a lifetime trip awaits you. Step into a space designed for relaxation and functionality. The suite is enhanced with Internet, Satellite Dish, and TV. Washing facilities available. Book your stay today!

Top guest favourite
A serene saltwater pool reflects sunlight, surrounded by tropical foliage and decorative lanterns. The tranquil waters capture the scenery of Coral Bay, with boats gently bobbing on the horizon. Lush greenery enhances the peaceful ambiance of the outdoor space.
Flat in St. John
5.0 out of 5 average rating, 112 reviews

Into the Mystic Lower Suite with POOL and VIEWS!

Into the Mystic Lower Suite is a beautifully finished suite located in peaceful Coral Bay, St. John. Offering every amenity you need for a perfect vacation - Salt water pool, high speed Wi-Fi, DISH TV, electric grill, solar with back up batteries & more. Our lower-level suite is your own private escape after a day exploring St. John's beaches and hiking trails. We offer a beautiful indoor living space & a peaceful balcony which showcases our view of Coral Bay & beyond.

Guest favourite
A spacious pool area is surrounded by lounge chairs, with lush greenery and hills in the background. The pool features distinct sections, including a shallow area. Bright blue skies and scattered clouds add to the inviting atmosphere.
Flat in Tortola
4.93 out of 5 average rating, 43 reviews

Orchid Bloom pool/beach nest

Orchid bloom is privately owned nestled on the premises of the magnificent Wyndham Resort Hotel on Lambert Beach. This unit boast a comfortable, private, first floor, garden view, poolside side apartment. Fine dining Restaurant on premises as well as, gym in a picturesque environment which lends itself to relaxation and rejuvenation. Just ten minutes drive from the airport, with magnificent hill and ocean views. Make Orchid Bloom the place for your next BVI vacation.

Top guest favourite
An aerial view showcases Sailors Cottage perched on a hillside, overlooking Coral Bay and the surrounding islands. The property features a private pool and spacious deck, framed by tropical greenery. The scenic landscape includes patches of water and distant hills, emphasizing its tranquil setting.
Home in St. John
5.0 out of 5 average rating, 99 reviews

Stone Cottage with a pool and gorgeous view

Sailors Cottage is located on a knoll overlooking Coral Bay with views to the BVIs. We are a 5 minute drive to restaurants in Coral Bay, 20 minutes to the pristine National Park beaches. The pool is private with a spacious pool deck, lounge chairs, comfortable seating and a picnic table for family BBQs. It’s the perfect place for morning coffee, sunset cocktails and star gazing. Or a relaxing day playing in the pool. The bedrooms have A/C for a great nights sleep.

Top guest favourite
A bright living area features large windows that frame scenic mountain views. A light-colored sofa and two armchairs surround a wooden coffee table, complemented by a natural stone accent wall. Decorative plants add a touch of greenery, while a television is mounted on the wall.
Flat in Cruz Bay
5.0 out of 5 average rating, 126 reviews

Esperance~Pool~New~National Park

Spacious 2BR, 2BA luxury apartment in Fish Bay Skytop with full kitchen and washer/dryer. Both bedrooms feature Loom & Leaf memory foam mattresses. King bedroom with en-suite bath, second bedroom with queen bed and bathroom across the hallway. Smart TV with Netflix and streaming apps (no cable). 10 min drive to Cruz Bay dining, shopping, groceries, 25 min to North Shore beaches. 4 ft shared pool and BBQ with two other apartments.

Guest favourite
Flat in Road Town
5.0 out of 5 average rating, 17 reviews

Winter’s Nook - Caribbean Escape

Welcome to Winter’s Nook—a cozy studio in a secure Road Town enclave, perfect for solo travelers or couples. Steps from the financial district and walking distance to shops, banks, and restaurants. Enjoy a shared pool, coin laundry, and designated parking. With security cameras on-site and a peaceful vibe, it’s your ideal Caribbean base for work or play. Comfort, convenience and charm all in one.

Top guest favourite
An inviting plunge pool is situated on a wooden deck, surrounded by lush greenery and offering panoramic views of the turquoise waters below. The horizon showcases distant islands under a bright blue sky dotted with fluffy clouds.
Villa in Brewers Bay
4.88 out of 5 average rating, 86 reviews

Villa Matija

Villa Matija is nestled comfortably into the hillside overlooking Brewers Bay on Tortola in the British Virgin Islands. Allow yourself a little luxury and be eco-friendly at the same time! Villa Matija (pronounced ma-TEE-ya) sits above Brewers Bay with an outstanding view of Jost Van Dyke and several other smaller cays & islands. On a clear day you can see Puerto Rico (about 70 miles away)!

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