Vacation rentals in The Settlement

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Top-rated vacation rentals in The Settlement

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Top guest favorite
The modern villa is prominently positioned on a hillside, featuring a spacious terrace and an inviting pool. Large glass doors enhance the seamless connection between indoor and outdoor areas. Lush greenery surrounds the property, adding to its serene environment.
Villa in Road Town
5 out of 5 average rating, 33 reviews

Luxurious 4 bed with pool and spectacular views

Welcome to The Lighthouse, our beautiful new build four bed, four bath villa, perched on the hillside overlooking the marinas of Road Town. This stylish, centrally located home, with its modern aspect, cool breezes, pool, ample entertaining space and work-from-home office has easy access to squash, tennis, gym and restaurant just two minutes away on the Pasea Estate at the Tortola Sports Club and is less than ten minutes to unspoiled pristine beaches and the upscale restaurants of Tortola.

Guest favorite
A panoramic view of Cane Garden Bay is presented, showcasing turquoise waters meeting a sandy beach. Lush greenery lines the coastline, while hills in the background are dotted with residential homes, creating a serene landscape that captures the beauty of the island.
Apartment in Cane Garden Bay
4.89 out of 5 average rating, 102 reviews

Windy Hill Sea View

Windy Hill Sea View overlooks the stunning Cane Garden Bay, offering panoramic views of the ocean and neighboring islands. This spacious one-bedroom ocean-view apartment provides a comfortable and welcoming retreat for your stay in the British Virgin Islands. Located on Windy Hill in Tortola, the apartment sits in a quiet, low-traffic neighborhood, perfect for relaxation. Windy Hill Sea View is a non-smoking apartment, ideally suited for couples or solo travelers seeking a peaceful getaway.

Top guest favorite
An aerial view captures the serene landscape of Anegada, showcasing sandy beaches meeting clear, turquoise waters. The green vegetation surrounds several cottages set along the shoreline, with winding paths leading through the property, emphasizing the peaceful and remote atmosphere.
Villa in Anegada
4.94 out of 5 average rating, 89 reviews

Loblolly Beach Cottages: GREEN (1 bedroom/1 bath)

“Green Cottage” Caribbean cottage charm that is unique to Anegada, but now with beautiful modern amenities and a property with lots to do! Location is everything here. Step out of your cottage and into the sand at beautiful Loblolly Bay. We located on one of the most beautiful beaches and coral reefs in the Caribbean (and on most days you will have it all to yourself). Snorkeling, relaxing, walking to get a drink, stargazing, or taking an adventure tour. A private slice of heaven!

Guest favorite
An open living area features retractable sliding glass doors that offer stunning views of the blue Caribbean Sea and nearby sailboats. Natural wood ceilings complement sleek concrete floors. Comfortable seating arrangements include a sofa, chairs, and a workspace, enhancing the inviting atmosphere.
Villa in Leverick Bay
4.97 out of 5 average rating, 132 reviews

Seascape Guest House, Leverick Bay, Virgin Gorda

Seascape Guest House is an exquisitely designed one bedroom villa on Virgin Gorda in the British Virgin Islands. Just completed, the spacious 650 SF villa is sustainably designed and features an open plan kitchen and living area with master bedroom and ensuite bathroom. The screened in patio and roof deck provide additional outdoor space to relax and take in the stunning ocean views. A short walk from all the amenities of Leverick Bay Resort, Seascape is a one of a kind BVI retreat.

Guest favorite
Villa in Nail Bay
4.84 out of 5 average rating, 25 reviews

1 Paradise Lane-A Modern Tropical Beachfront Oasis

Our street address is indeed 1 Paradise Lane. This centrally air-conditioned 2-BR 2.5 bath villa is situated within a lush tropical garden bordering the private Nail Bay Golf Course & the sea. Our 1,000+/- sq. ft roof top deck with glass railings is perfectly situated to capture the best sunset views and the never-ending boating traffic on the Sir Francis Drake Channel. Please note that Sunset Watch and 1 Paradise Lane share a pool and they can be rented together as a 3 BR villa.

Guest favorite
A swing is situated beneath a white trellis, surrounded by lush greenery and overlooking the bay with moored boats. The sunset casts a warm glow over the scene, highlighting the peaceful atmosphere and natural beauty of the tropical landscape.
Apartment in Cane Garden Bay
4.97 out of 5 average rating, 34 reviews

Cane Garden Bay 2 bed Apt

Just a short walk to the beach and vibrant local restaurants, this cozy and modern retreat offers breathtaking views of the bay and unforgettable sunsets. The apartment is equipped with modern amenities, including two flat-screen TVs, washer/dryer, and a fully stocked kitchen. Perfect for couples, families, or friends seeking comfort and convenience in a beautiful, tropical setting. Your island getaway awaits! Rental cars available at an additional $70-80 per day.

Guest favorite
A spacious outdoor area features a large private pool surrounded by a wooden deck. Comfortable lounge chairs are positioned for relaxation, and a dining table is arranged beneath a shaded pavilion, with lush tropical greenery framing the scene.
Home in Princess Quarters
5 out of 5 average rating, 5 reviews

Salt Spring Villa & Spa - Superb

This is the perfect sanctuary for one family or two couples. Separated by a beautiful and lush tropical Garden, Salt Spring Villa is the sister villa to Red Rock Villa and Spa. It was built by the same architect and decorated with a similar tropical and balinese style. The biggest pool of private villas invites you to take a swim anytime in total privacy. Two king size beds in spacious bedroom suites serve your longing for comfort and quiet. A special place indeed.

Guest favorite
An outdoor dining area features a wooden pergola providing shade over a large table and chairs, complemented by a hammock nearby. A sparkling pool is set against a backdrop of breathtaking ocean views, while lush greenery and decorative plants enhance the tranquil setting.
Villa in Trunk Bay
4.96 out of 5 average rating, 25 reviews

Luxury Villa near Beach~ Private Estate~ Pool

This listing highlights Odyssea House, our 2-bedroom sanctuary within Odyssea Villas in Tortola. Enjoy luxury with stunning Trunk Bay views, modern amenities, and pool access. Perfect for those seeking tranquility and natural beauty, it's a short stroll from secluded beaches. Interested in more space? Explore our 3-bedroom option in our other listing, with the addition of the nearby "Odyssea Oasis" - a one bed unit with rooftop entertainment, lawn and jaccuzi.

Top guest favorite
Villa in Tortola
5 out of 5 average rating, 25 reviews

Villa Soleil, 3 BDs, Pool, Walk to the Beach

Villa Soleil is a luxuriously appointed vacation villa on the North shore of Tortola, British Virgin Islands.  Privately nestled in the tropical hillside overlooking the paradisiacal Trunk Bay beach, this villa emanates the perfect balance of sophistication, style and comfort. There are 3 bedrooms, 2.5 bathrooms and 2 outdoor stone showers.  Choose from, a King, Queen or King with Double/Twin bunk (ideal for kids/family/couple)

Top guest favorite
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)!

Top guest favorite
Apartment in Road Town
4.98 out of 5 average rating, 49 reviews

2 Bedroom Apartment in Great Mountain

Experience this spacious 2-bedroom, 1-bathroom apartment nestled in the peaceful hills of Great Mountain. Just a 7-minute drive from the capital, Road Town, this inviting retreat offers the perfect blend of comfort and convenience. Unwind and feel at home as you take in the breathtaking views and enjoy the tranquility of nature in this hidden gem your perfect home away from home.

Guest favorite
A small, charming shack is nestled among large boulders, showcasing a wooden deck with seating. Light blue shutters frame the windows, allowing natural light to enter. Lush greenery surrounds the structure, while the sky is a bright blue with scattered clouds.
Hut in Tortola
4.95 out of 5 average rating, 188 reviews

Tiny Cozy Shack 8 minutes from Beef Island airport

Located in a breezy valley on the East End of Tortola overlooking Beef Island & Virgin Gorda. Nestled among boulders where you can enjoy beautiful sun rises. Simple tiny room (8’x10’) with full size bed with a private bathroom + outdoor shower, NO hot water.. Outdoor kitchenette with mini fridge, stove, kettle, toaster. Electricity, solar lights, fan and WiFi.

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