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Vacation Rentals in The Settlement

On the beach, white sand, sun loungers, beach umbrellas

"Nice property with beautiful beach just steps away from your door. "

"Nice personal attention. Owner was extremely attentive bringing us home made pastries and continously looking out for us. Great views from the balacony. "

"This is a great place for a family vacation. The house is in great condition and has all the amenities you may need. It is located in a place to itself but at the same time, close to everything. Virgin Gorda is amazing. Owners were great in helping us get there, and with many tips that made our vacation great!"

On the beach, sun loungers, beach towels

"What a beautiful home and location. Our host Mindy was wonderful!! The home is recently renovated, so clean and has everything you need to enjoy your stay. A close drive to great restaurants and sites to see. You must go and stay at Drakes View. We will be back next year for some more fun. "

"The house is in a beautiful location. It’s well equipped and well laid out for different generations to co-mingle. The owners are easy to deal with and they will go into great pains to make your stay comfortable and deal with any issues or requests."

"When I arrived on the property I had a sense of arriving at the cottage. We walked into our private veranda and it felt like home but in the Caribbean. I read books in the hammock, we played cards at the dining table. We swam off the private dock. The house was equipped with anything and everything. It was spacious. We all had our our rooms with private bath. I could have stayed forever. Only downside, the only local grocery store was crazy expensive. We drove into town and found a much cheaper...

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Other types of properties in The Settlement you may be interested in

"Loved everything "

includes taxes & fees

$267 per night

May 18 - May 19

Find out more about The Settlement

Everything you need to know about The Settlement vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the The Settlement vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect The Settlement vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

The Settlement vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in The Settlement. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit The Settlement in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on The Settlement rentals

At Expedia, we put the best The Settlement vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top The Settlement rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream The Settlement vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around The Settlement. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Recent reviews of The Settlement properties

5/5 Excellent

Couple escape

"Saba Rock is a nice place to stay for a weekend escape. Breakfast was included with the room and is a complete breakfast with options to choose. We had dinner twice and food is good. The room is very nice, especially the shower space is great. It also has two sink very comfortable. Although I have to mention that the right sink was clogged. I reported to the cleaning lady but it was not solved. We managed with the other one. But apart from that the room is very comfortable. The decoration has many details. The place renovation was carefully thought and you could notice the details. Employees are very friendly and educated toward the guest. It is a place I will return."

A verified traveler stayed at Saba Rock Resort

Posted 10 days ago

New Construction Oceanfront Home/Pool Private Walk To Beach

5/5 Excellent

Beauty on the bay

"Beautiful view of Nail Bay, lovely decks and pool with beach a short walk below. House is very tastefully done and well equipped. Bedding is excellent and very comfortable, outdoor showers are awesome. Mindy (Property Mgr.) is wonderful and lives nearby. “Rightway” grocery mart has about everything you would need. (Bring your own tissues, shower soap and shampoo, but hand soap is provided.) "

A verified traveler stayed at New Construction Oceanfront Home/Pool Private Walk To Beach

Posted 2 months ago

Luxury Villa With Fantastic Views Steeped In Privacy

4/5 Good

Our experience

"The house is in a beautiful location. It’s well equipped and well laid out for different generations to co-mingle. The owners are easy to deal with and they will go into great pains to make your stay comfortable and deal with any issues or requests."

A verified traveler stayed at Luxury Villa With Fantastic Views Steeped In Privacy

Posted 4 months ago

VERY Private, Spectacular, Waterfront Location

5/5 Excellent

Beautiful seclusion

"Family of 6 had plenty of room to spread out! The home sits above a beautiful cove, with some construction of a tennis court underway. The cove is very pretty, appears to be shallow water, but with the weather there was quite a bit of debris. The cows enjoy the beach every morning during their grazing time. Humorous to see! The beds were very comfortable, with house management cleaning mid-week, linens were always fresh. AC units worked very well during a very hot spell. Air circulation was pretty decent during rolling power outage from the main electric provider. The road definitely requires a jeep, so heed property description well- it is quite literally a cow path. The pool was quite relaxing, but did need a bit more maintenance on the pump to remove the debris and bugs. There are quite a bit of stairs to climb to reach the entrance, so be prepared if you are traveling with less mobile people. Ample refrigerator space, some provided extras like kitchen supplies. Lots of cooking utensils. Word of advice- food supplies in stores are not like you would find on mainland. So potentially look into delivery service from Tortola or pack your own. The house/property manager was very helpful and responsive to questions. Overall we had a wonderful time!"

A verified traveler from Medina, OH stayed at VERY Private, Spectacular, Waterfront Location

Posted 10 months ago

Frequently asked questions

Can I find a vacation rental in The Settlement?

Yes, we give you a choice of vacation rentals near top attractions in The Settlement, or you can go with a secluded option if you want a relaxing place to stay. The Settlement is known for its beaches and seafood restaurants.

What's the top vacation rental that The Settlement has to offer?

New Construction Oceanfront Home/Pool Private Walk To Beach: This vacation home rental near The Settlement is located on the beach and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What’s there to see and do in The Settlement?

Loblolly Bay Beach and Loblolly Bay are a couple of lovely local spots to get outside and enjoy nature. Oil Nut Bay Beach and Bitter End Gardens are a couple of places you'll find in the larger area.

What’s a vacation rental in The Settlement like?

A vacation rental is a private property you can stay in for a long or short time in The Settlement. Vacation rentals offer amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and bustling concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a small group gathering.

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The Settlement Vacation Rentals

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Check prices for these dates

Vacation Rentals in The Settlement

Sea Grape Villas

Four Diamonds Park Villas

Mango Bay Resort

Gordian Terrace

VERY Private, Spectacular, Waterfront Location

New Construction Oceanfront Home/Pool Private Walk To Beach

Luxury Villa With Fantastic Views Steeped In Privacy

Virgin Gorda Villa Rentals

Nail Bay Resort

Villa Sol Mate

Other types of properties in The Settlement you may be interested in

Sea Grape Villas

Four Diamonds Park Villas

Saba Rock Resort

Find out more about The Settlement

Recent reviews of The Settlement properties

Saba Rock Resort

New Construction Oceanfront Home/Pool Private Walk To Beach

Oil Nut Bay

Mango Bay Resort

Luxury Villa With Fantastic Views Steeped In Privacy

VERY Private, Spectacular, Waterfront Location

Leverick Bay Resort and Marina

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