Vacation rentals in The Settlement

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Top-rated vacation rentals in The Settlement

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Guest favorite

Apartment in Road Town

4.87 out of 5 average rating, 210 reviews

Trunk Bay downstairs self-contained room

Hi! We paused this listing first because it was 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!

Dec 5 – 12

G$22,346 GYD per night

Guest favorite

Villa in Anegada

4.9 out of 5 average rating, 50 reviews

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

Just renovated! *All reviews before 2021 are pre-renovations. The same Caribbean cottage charm, but now with beautiful modern amenities. 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 Big Bamboo for a drink, stargazing, or taking an adventure tour. A private slice of heaven!

Jul 1 – 8

G$45,805 GYD per night

Guest favorite

Villa in Virgin Gorda

4.95 out of 5 average rating, 55 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.

Dec 13 – 20

G$106,595 GYD per night

Guest favorite

Villa in Virgin Gorda

4.97 out of 5 average rating, 78 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.

Dec 5 – 12

G$91,232 GYD per night

Guest favorite

Guesthouse in Tortola

4.96 out of 5 average rating, 46 reviews

The Anchorage- Studio apt above Cane Garden Bay

We are back with a newly renovated guest room! Charming studio apartment on lower level of provencal estate, centrally located in the hills above Cane Garden Bay w/view of Jost Van Dyke & surf at Cane Garden Bay. Private terrace w/outdoor dining. Includes use of shared pool. Small trail through 1 acre of undeveloped but landscaped jungle. 4WD vehicle required. Property is 10 min drive to Road Town & Cane Garden Bay, 5 min to Nanny Cay. 30 min to airport & west end.

Jan 15 – 22

G$41,302 GYD per night

Superhost

Villa in Trunk Bay

4.9 out of 5 average rating, 10 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.

Oct 21 – 28

G$185,527 GYD per night

Guest favorite

Guesthouse in Tortola

5.0 out of 5 average rating, 12 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.

Nov 16 – 23

G$25,899 GYD per night

Guest favorite

Apartment in Cane Garden Bay

4.92 out of 5 average rating, 53 reviews

Windy Hill Sea View

Windy Hill Sea View overlooks the beautiful Cane Garden Bay with a panoramic view of the ocean and neighboring islands. This spacious one bedroom ocean view apartment offers a comfortable atmosphere to stay in during your visit to the BVI. This apartment is located on Windy Hill in Tortola in a very quite low traffic neighborhood . Windy Hill Sea View is perfect for couples or just one person.

Dec 7 – 14

G$26,803 GYD per night

Guest favorite

Villa in Brewers Bay

4.84 out of 5 average rating, 43 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)!

Nov 11 – 18

G$87,069 GYD per night

Guest favorite

Hut in Tortola

4.94 out of 5 average rating, 136 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.

Dec 23 – 30

G$22,114 GYD per night

Guest favorite

Villa in Nail Bay

5.0 out of 5 average rating, 7 reviews

Boulder Crest, Pool, March 20th to 26th $700pn

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.

May 9 – 16

G$154,606 GYD per night

Guest favorite

Home in Tortola

4.93 out of 5 average rating, 122 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.

Aug 13 – 20

G$57,177 GYD per night