Vacation rentals in The Settlement

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Top-rated vacation rentals in The Settlement

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Central

4.94 out of 5 average rating, 67 reviews

‘Lots Of Knots’ cute Upper Carolina cottage

Lots Of Knots is a cute cottage on Upper Carolina in Coral Bay. Great outside spaces to appreciate the views and breeze. Close to Northshore, Eastend and South beaches, paved access no need for a 4 wheel drive. Coral Bay shops and restaurants just down the hill, it catches any breeze blowing from the south up through Coral harbor. Harbor and valley views from the front deck, valley view from the back deck with 4 person hot tub, total privacy with no neighbors. Perfect for a romantic getaway.

Top guest favorite

Villa in Tortola

5 out of 5 average rating, 29 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 Long Bay in West end of Tortola

4.95 out of 5 average rating, 19 reviews

Cozy Beachview Retreat Studio For Couple | Balcony

This cozy upper floor studio apartment is the perfect size for a couple looking for an idyllic beach vacation. Your accommodations are equipped with a king bed, wi-fi, TV and AC as well as a private bathroom w/ shower. The kitchen includes a cooktop, refrigerator, & microwave as well as an air-fryer. One of the longest and most romantic beaches in the Caribbean is just a 2 minute walk down the hillside. Your expansive balcony provides stunning views of the mesmerizing oceanfront vista.

Guest favorite

Guest suite in Brewers Bay

5 out of 5 average rating, 23 reviews

Newly updated, stunning views, footpath to beach

You will be close to everything when you stay at this centrally-located, stylish getaway. Situated on the hillside of Anderson Pt of Brewer’s Bay, 60ft above the white sandy beaches- you can take a forrest foot trail to the sparkling waters of the caribbean sea within 5 minutes. If you love to explore, you will find the entry to one of the islands national parks within 1 minute from our driveway. Bring the kids as there are netted hammocks below the avocado trees and a wooden playhouse.

Top guest favorite

Villa in Anegada

4.93 out of 5 average rating, 70 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

Cottage in Saint John

4.94 out of 5 average rating, 121 reviews

"Ocean" 1 Bedroom in The Garden of Eden

Experience ocean views, AC-cooled bedroom comfort, solar power and a spacious deck in this new solar-powered cottage. Part of a unique collection, it shares an infinity waterfall plunge pool with another cottage (two more cottages coming in 2025). Enjoy constant breezes, afternoon shade, and magical moonrises from the “Ocean” cottage. Guests have 24/7 on-site concierge service and assistance, with full vacation planning by a Superhost experienced in welcoming first-timers to St. John.

Superhost

Apartment in Virgin Gorda

4.93 out of 5 average rating, 41 reviews

Bayview Vacation Apartments - Two bedrooms

Full size apartments hidden between lush tropical gardens. Interior decorated in a fancied Caribbean style. Great location for quick access to let you get involved in all activities around the island but quiet and peaceful. location, location, location- 1 minute walk to Dixies fast food.- 30 seconds walk to Bath and Turtle Restaurant.- 2 minutes walk to ferry terminal.- 4 minutes Drive to ONLY airport (VIJ)- $3 pp taxi to the World Famous Baths.- 2 minutes walk to St.Thomas Bay Beach

Guest favorite

Home in Coral Bay

5 out of 5 average rating, 28 reviews

Perfect Pool Villa close to Maho Bay & VI NAT PARK

"All About the View" is a stunning 2 Bedroom 2.5 Bath St John vacation rental with huge views over the BVI and beyond. Easy access, just 5 minutes to Maho Bay with a Pool, private baths, WIFI and all of the amenities. This mountain top gem is the perfect 2 bedroom rental. Big views of Coral Bay, Hurricane Hole, The East End and beyond to all of the British Virgin Islands. Modern and tasteful, spotlessly clean and bright with azure ocean views spilling into every room.

Superhost

Guest suite in Tortola

4.88 out of 5 average rating, 145 reviews

Cane Gdn Villa 2 bd 2 bath for 2-6

Beautiful new 2 bdrm villa in Cane Garden Bay, steps to beach, restaurants & taverns. Villa has been totally renovated including split air conditioning in bdrms, fresh new baths kitchen w granite n stainless. Beach chairs. Price based on 2 guests using 1 bedroom, $40 per person per night extra using 2nd bedroom. Comprises upper level right side of house in pic, we have self contained water system and power if needed. WiFi working most of time.

Guest favorite

Villa in Tortola

4.94 out of 5 average rating, 18 reviews

Sand Dollar- overlooking Long Bay Beach

Escape to this tranquil retreat with its stunning panoramic views, spectacular sunsets, gentle breezes, and the lulling sound of the waves. Sand Dollar is nestled in the prestigious private Belmont Estate and boasts views of Long Bay Beach, the Windward Passage, and Jost Van Dyke. It is only a 3-minute walk to Long Bay Beach and a ~16-minute walk (or short drive) to the more sheltered Smuggler’s Cove, among the loveliest beaches in Tortola.

Guest favorite

Home in Long Bay

4.93 out of 5 average rating, 29 reviews

Elegant House in paradise

Sugarloaf house a designers dream, Sugarloaf, offers a romantic setting, situated in a tropical garden location, with a short walk to two of Tortola’s finest white sand beaches. The House offers everything you could need to make a wonderful vacation, alfresco dining, views of the Caribbean Sea, sparkling turquoise pool and flower filled sundeck. You may never want to leave this Caribbean version of heaven!

Guest favorite

Condo in Road Town

4.89 out of 5 average rating, 18 reviews

Cooper Bay View

Come spend your best vacation ever, here at Cooper Bay View, in the beautiful British Virgin Islands! We are centrally located on Fahie Hill, just off the ridge road, overlooking the gorgeous North Shore! Enjoy island living in this 2 Bedroom 2 Bathroom retreat. Just a 7-minute drive to Road Town where you will find great restaurants, shopping, and a local treat or two.

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What guests are saying

Johnny Horn Trail House St. John

4.79 out of 5 average rating, 14 reviews1 month ago

We stayed for four nights, just the two of us. Loved every minute. In fact, while we intended to eat out most nights for dinner, at the end of each day we were eager to return to the house, cook a meal, and relax on the porch overlooking the bay. Kitchen was well-stocked, and everything you might need is a mile away at the Love City Market (it is a little costly, fyi). The outdoor shower was a highlight, as was the view each morning from the bedroom. The open floor plan was also lovely, and the house felt very private and spacious. I won't comment much on the road, as other guests already have. I will say this: the first time, we thought, halfway up, that we might have been on the wrong road! But by the end of the stay we were mostly used to it. Definitely need four wheel drive (thankfully that's all the rental places have anyway). We would happily come back. Wish we were there now!

Home in Coral Bay

What guests are saying

Villa with kitchenette 1BR

5 out of 5 average rating, 5 reviews4 weeks ago

This is the perfect location for a very peaceful and restful stay on Tortola. The host was really good at communicating both before and throughout our stay. One minor issue with the bathroom basin plug was resolved straight away. The garden area, pool and small beach were all delightful, though loungers could do with an upgrade (a very minor matter). Fall asleep and wake to the sound of the sea and if you’re really lucky watch a pelican fishing right in front of you. We saw it most mornings and late afternoons during our stay. Probably best to have a hire car available though taxis easy to organise. We also used the local bus service, which was ‘an experience’, one I’m glad we had. Would we go back? It’s a very long way from Europe! But we both really enjoyed our stay and, though not as young as we used to be, would love to come again. We had some important communications to make during our stay and excellent WiFi enabled us to do it. Thanks Justin and all the staff.

Apartment in west end

What guests are saying

Just Right Villa St John

4.91 out of 5 average rating, 22 reviews2 months ago

We loved staying at Greg‘s place! Best value on the island in my opinion. Very close to the national Park beaches, which made it super convenient. That side of the island is quiet. It was close to centerline Road, which made it easy to get to Cruz Bay for the few things we needed to do there. Greg was a great host and communicated well and helped us figure out any problems that we had. Make sure you rent a jeep as the driveway is very steep. Most driveways on St. John are however. Overall it was a great place to stay and we will stay there again!

Villa in Central

What guests are saying

Seaside Serenity apt

4.88 out of 5 average rating, 42 reviews2 weeks ago

Absolutely loved my stay at this Airbnb on Tortola! The unit was impeccably clean, thoughtfully designed, and perfectly equipped with everything I needed, from a full kitchen to cozy outdoor seating. I left the doors open while I was there to take advantage of the lovely breeze. And while the unit has air conditioning O didn’t turn it on until I went to bed. The host was incredibly kind, responsive, and full of local tips that made my trip extra special. Whether you’re looking to relax or adventure, this place is a perfect home base while you’re on Tortola.

Apartment in Tortola

What guests are saying

Guava Road Apartments/Palm Unit

5 out of 5 average rating, 20 reviews24 months ago

First of all, the hosts are amazing. Patricia followed up throughout my stay without “hovering.” Alphonso greeted me with patience (it was a long day of travel and my brain wasn’t functioning on all cylinders!) and a big smile. He suggested we get takeaway from Sebastian’s, an easy walk, before they closed for the evening. The food was delicious. The chicken wings are definitely hot…just as I hoped! Settling in was easy. I immediately felt relaxed especially on the porch listening to the neighborhood settle in and then for coffee the next morning. The beach at Apple Bay is clean, private, the water is stunning to look at and refreshing. Patricia and Alphonsos place is ideal for anyone who appreciates immersing themselves in an off the beaten path location. If you yearn to explore everything Tortola has to offer you can also rent a car directly with Alphonso.

Apartment in West End

What guests are saying

Traveler Palm Cottage, Newly built home sleeps 6

4.93 out of 5 average rating, 57 reviews2 months ago

Colleen’s place was wonderful!! Staying on the Coral Bay side of the island was a nice change of pace for us. The house was secluded and quiet. The flowers, fruit trees, birds and lizards added to the beauty. The kitchen had everything we needed to cook dinner in a few nights. The hot tub was a wonderful way to relax in the evenings. The beach chairs and cooler were an added bonus. The location was great, we enjoyed getting to the East End beaches easily but also being close to our favorite beach, Maho. It was also nice being so close to the Love City market grocery store. Colleen’s place was the perfect place for our family of 4!! Thank you!!

Home in Saint John

What guests are saying

New! Cooper's Friendly Club

5 out of 5 average rating, 4 reviews12 months ago

It was perfect for my needs for a few days, within walking distance to restaurants and a mini market. The place supplied all the basics that I required. It was beautifully clean and organised. Charles is a fantastic host. Very helpful and friendly. I definitely recommend this stay if you're looking for something away from the hustle and bustle of the tourist centres. Thank you Charles

Vacation home in Leonards

What guests are saying

Sundowner romantic 1BR beachfrontvilla privatepool

4.93 out of 5 average rating, 72 reviews1 month ago

There’s no words to describe this lovely Villa , the view and the location except that it’s a piece of Heaven on Earth. You just have a car to get around and driving isn’t for the faint at heart. The cliffs on all the Mountains will take your breathe away. We will be back ❤️

Villa in Virgin Gorda

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