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Leeward Settlement vacation rentals

We found 297 vacation rentals — enter your dates for availability

Discover a selection of 49 homes, 167 villas, and vacation rentals in Leeward Settlement that are perfect for your trip. Vacation rentals offer the best amenities for your stay with friends, family, or just your pet, such as parking and a fireplace. You're sure to find a rental that has what everyone needs, including options that are accessible or non-smoking.
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Barefoot luxury in Leeward Settlement

Set on the northern tip of Providenciales, Leeward Settlement is your ticket to a tropical paradise. The laidback community is a gateway to the Turks and Caicos Islands, a string of sandy cays fringed by sugar-white beaches, swaying palms and translucent water. While Grace Bay Beach makes a dreamy first impression, Leeward Settlement is just as enchanting. A favorite with longtime vacationers, Leeward Settlement vacation rentals champion barefoot luxury. Take your pick from condos, cottages and spacious villas.

Conch and cocktails in Leeward Settlement

Most visitors arrive on Providenciales in search of well-deserved R&R. Leeward Settlement vacation rentals deliver, with oceanfront infinity pools and sun-drenched decks. Throw in sunset cocktails and you'll quickly find yourself slipping into island time. When you've had your fill of gorgeous beaches and swaying hammocks, why not check out attractions like the Caicos Conch Farm? It cultivates conch for the entire Bahamian Archipelago, with tours offering a behind the scenes glimpse at the entire process, from shell to seafood restaurant.

Tropical winters in Leeward Settlement

Winter is high season in the Turks and Caicos Islands, when the archipelago enjoys clear skies, calm waters and balmy temperatures. Expect bigger crowds over busy periods like Christmas and the winter school break. Planning a family getaway to the tropics? With spacious living areas and affordable price tags, self-contained Leeward Settlement vacation rentals run circles around hotels. If you don't mind the occasional rain shower, consider visiting in April or May. This is considered a sweet spot, with quieter beaches and highs that hover around the 80s. You'll also sidestep Atlantic hurricane season, which rolls from June to November.

Aquamarine lagoons in Leeward Settlement

Leeward Settlement is perched on the northernmost tip of Providenciales, the most populated island in the Turks and Caicos. The Atlantic archipelago is made up of 40 low-lying coral islands encircled by barrier reefs and underwater sea walls. As well as a myriad of ravishing beaches, Providenciales is also home to gems like Chalk Sound National Park. The lagoon stretches for 3 miles and is strewn with tiny islets that rise up from the turquoise-hued water. Visit in winter and you'll catch 1000s of humpbacks cruise through the Turks and Caicos Islands on their annual migration.

Transportation options to and around Leeward Settlement

Fly into Providenciales Intl. Airport (PLS), the closest airport, located 8.3 mi (13.4 km) from the city center.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Leeward Settlement?
Villas are the most popular style of vacation rental in Leeward Settlement, according to our data. Even if you’ve got a different idea about what you’d like, Vrbo has vacation homes in all sizes and shapes. Take a look at our options to find your perfect fit.
How much does it cost to rent a vacation rental in Leeward Settlement?
Several things determine what you’ll pay for your vacation rental in Leeward Settlement, such as the length of stay, type of property and season. However, all our vacation homes have something in common — unbeatable value. Simply add your travel dates to find your perfect fit.
How much does it cost to rent a beach house in Leeward Settlement?
Prices for beach houses in Leeward Settlement vary depending on the size and type of the property and when you plan to travel. Simply enter your dates of travel into Vrbo and how many guests to view your vacation rental options and prices. From there you can use the filters to tailor your search by ratings, nearby activities, amenities and more.
Are there pet-friendly vacation rentals in Leeward Settlement?
Yes. There are. Take your pick of 173 vacation rentals that allow pets in Leeward Settlement on Vrbo. Our furry best friends also deserve a getaway, so simply use our search function for pet-friendly vacation rentals to find a perfect property where your doggie can lap up the good times.
Can I rent a house with a pool in Leeward Settlement?
Grab your swimming gear and pool noodle, because there are 134 houses with a private pool in Leeward Settlement. Make a booking at one of these terrific vacation homes and you’ll enjoy pool days every day. Simply enter your travel dates into Vrbo, then use the “pool” filter to find the ideal place for a splashing good time!
What are popular rental amenities in Leeward Settlement?
A nearby river, a fireplace and ski-in/ski-out facilities rank as the most popular rental amenities in Leeward Settlement. Whether you plan to travel on your own, with your spouse or as a family, Vrbo can help you find a vacation rental that matches your tastes with all the features you need.
Are there large group vacation rentals in Leeward Settlement?
You’ll discover 67 vacation rentals in Leeward Settlement that can host 10 or more guests. Whether you’re organizing a get-together with extended family or a celebration like a birthday, there’s ample space to get your favorite people together under the same roof.
Are there vacation rentals in Leeward Settlement that welcome kids?
Bring the entire group together for the adventure of a lifetime in Leeward Settlement at one of our 163 family-friendly vacation rentals. Many of these stays offer conveniences that are just perfect for trips with youngsters, like dining rooms, multiple bedrooms and swimming pools. Simply check the “Properties good for families” filter and pick your favorite.
Are there one-bedroom vacation rentals in Leeward Settlement?
Take your pick from 25 one-bedroom rentals in Leeward Settlement. Whether you’re looking for a townhouse or a fancy condo, Vrbo’s one-bedroom properties are just right if you don’t need a lot of space. One of the perks of having your own pad? You won’t ever have to share your adventure with strangers.
Can I find two-bedroom vacation rentals in Leeward Settlement?
Take off with your besties and enjoy peace, privacy and comfort in one of the 21 two-bedroom vacation properties Leeward Settlement has to offer.
Are there vacation rentals with WiFi in Leeward Settlement?
Take your pick of 75 vacation rentals with WiFi in Leeward Settlement. If you’d like to disconnect from daily life on your vacation, but still need to be connected to the web, these getaways have just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Leeward Settlement?
You can choose from 154 Vrbo vacation homes with air conditioning in Leeward Settlement offering that cool, cool breeze and extra bit of comfort. Simply enter your preferred dates of travel and then make use of our filter tool to locate stays with air conditioning.
How old do you have to be to rent a vacation rental in Leeward Settlement?
The minimum age can vary across properties on Vrbo, so be sure to check the rules of the vacation home in Leeward Settlement you’re considering. But in general, it’s 16, 18 or 21.
How long can I rent a vacation rental in Leeward Settlement for?
It’s down to the Leeward Settlement property. To view a list of options offering extended stays, just type your dates and guest number into the Vrbo search page. You can look forward to having the entire place to yourself, along with home comforts such as air conditioning, a fully-equipped kitchen and a yard where the kids can burn off energy. Be on the lookout for any long-term stays that offer discounted weekly or monthly prices.
Does Vrbo offer discounts for vacation homes in Leeward Settlement?
Whether you’re after one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you’re sure to find some incredible deals and discounts on Vrbo. From short stays to extended vacations, we’ve got the ideal space for your next Leeward Settlement escape.

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