Vacation rentals in The Settlement

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Top-rated vacation rentals in The Settlement

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Superhost

Villa in Virgin Gorda

4.93 out of 5 average rating, 74 reviews

Sundowner romantic 1BR beachfrontvilla privatepool

Sundowner reigns as Virgin Gorda's most sought-after honeymoon villa. This majestic yet romantic beachfront villa, with a street address of 1 Paradise Lane within Nail Bay Estate, impresses guests with its royally inviting decor. Sliding glass doors on this villa's private patio lead to the inside dining and living areas, and the open-plan spacious gourmet kitchen. The view from the throne bed overlooks the turquoise sea and the cloud-strewn azure sky with colors custom-made in the Caribbean.

Guest favorite

Villa in Tortola

5 out of 5 average rating, 33 reviews

Gorgeous 4 bed villa with pool and amazing views

'Twin Oceans on Spyglass' is our beautiful 4 bed/4 bath villa at the West End of Tortola. Standing majestically on the hillside with beautiful views across the ocean to St John on one side and to Jost on the other. We are sure you will love this home, with its cool breezes, gorgeous pool and spacious entertaining areas. Just a few mins drive to Long Bay, Smugglers or any of the pristine deserted beaches on the North shore and just a five mins to the world renowned surf break at Apple Bay.

Guest favorite

Apartment in Road Town

4.89 out of 5 average rating, 232 reviews

Trunk Bay Spring - downstairs self-contained room

Hi! We paused this listing after being badly damaged by Hurricane Irma, and then due to Covid 19, but we're back – repaired and upgraded! The outdoor shower that our guests loved is still there, only now it has hot water. There's also a new kitchen made of hardwood we were able to salvage after Irma. Great news! The beach is still there, too, and still a just ten minute walk away. Always popular for being simple and beautiful in a fantastic location, now it's the same, but even better!

Top guest favorite

Villa in Anegada

4.93 out of 5 average rating, 76 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

Villa in Leverick Bay

4.98 out of 5 average rating, 112 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 Trunk Bay

4.95 out of 5 average rating, 21 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

Guesthouse in Tortola

5 out of 5 average rating, 61 reviews

Long Bay Surf Shack

"Location, location, location!" This rustic yet charming guest studio is nestled on a hillside above one of the most sought-after and beautiful resorts in the Virgin Islands. Just a two-minute walk to Long Bay Beach and Resort, which offers an amazing spa, beach bar and restaurant. This guest studio is perfect for a couple or a family of three. Hosts have lived in the BVI for 30 years and love to share local insights.

Top guest favorite

Home in Great Camanoe

5 out of 5 average rating, 8 reviews

Private Hilltop Villa with Boat

Enjoy our gorgeous hilltop paradise with easy access to beautiful swimming beaches, fantastic snorkeling reefs, and almost every form of water recreation imaginable. With a sweeping 280-degree panoramic view, the villa is designed to showcase the extraordinary beauty of the surrounding islands. An SUV and boat are included in the rental, ideal for exploring Camanoe and the surrounding islands.

Guest favorite

Villa in Brewers Bay

4.86 out of 5 average rating, 69 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)!

Guest favorite

Hut in Tortola

4.95 out of 5 average rating, 167 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 the sun rise. Simple tiny room (8’x10’) with full size bed has a private bathroom + outdoor shower, no hot water.. Outdoor kitchenette with mini fridge, stove, kettle, toaster. Electricity, solar lights and WiFi available.

Superhost

Villa in Nail Bay

5 out of 5 average rating, 9 reviews

Boulder Crest, Pool, Private, AC Throughout

Welcome to Boulder Crest Villa. Located amidst large island boulders, this private Virgin Gorda villa offers discerning travelers a paradisiacal setting for their next island retreat. Located 70 feet above the sea, the oasis sits just ten minutes away by foot is the pristine beach, and is augmented by a serene island landscape.

Guest favorite

Home in Tortola

4.94 out of 5 average rating, 148 reviews

Private One Bedroom Villa, HotTub, Amazing Views

Nestled on top of Cooten Bay in Tortola, British Virgin Islands, Cooten House has amazing views that will take your breath away. Whether you are looking for a romantic getaway, a place to relax and soak up the sun or all of that plus close proximity to great surfing spots, Cooten House will exceed your expectations.