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Leeward Settlement vacation rentals

We found 1,128 vacation rentals — enter your dates for availability

your current months are May, 2024 and June, 2024.
May 2024
June 2024
Discover a selection of 60 homes, 162 villas, and vacation rentals in Leeward Settlement that are perfect for your trip. Whether you're staying in a vacation rental with family or friends, you'll have the best amenities for spending time at your home away from home, which might include air conditioning and a pool. You're sure to find a rental for everyone's 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?

Based on our research, villas are the most desirable property type in Leeward Settlement. But of course, everyone's idea of an awesome trip can vary. Vrbo has vacation rentals in a variety of sizes and shapes, so you're sure to find the perfect fit.

How much does it cost to rent a vacation rental in Leeward Settlement?

Different things determine what you'll pay for your vacation rental in Leeward Settlement, such as the season, type of property and length of stay. But, all Vrbo homes have one thing in common — amazing value. Just add your travel dates to find your home away from home.

How much does it cost to rent a beach house in Leeward Settlement?

The average price for a vacation rental near the beach in Leeward Settlement will depend on when you're going and the style and size of property you want. You can easily find prices on Vrbo by entering the dates you'll be traveling. Then use the filter tool to choose the number of bedrooms and amenities that you need, like a pool, WiFi and air conditioning.

Are there pet-friendly vacation rentals in Leeward Settlement?

Pack up a suitcase for your pup because Leeward Settlement has 160 vacation homes that throw open their doors to pets. Let your four-legged pal have fun with the family at one of our pet-friendly vacation rentals on Vrbo. Simply enter your dates then check our "Pets allowed" filter box.

Can I rent a house with a pool in Leeward Settlement?

Mark the "pool" box in our handy filter tool and choose from 124 houses with private pools in Leeward Settlement on Vrbo. Morning swim, afternoon splash or midnight soak? Free time is up to you when your Vrbo vacation property has a swimming pool.

What are popular rental amenities in Leeward Settlement?

When it comes to rental amenities that people are looking for in Leeward Settlement, a firepit, a water view and a fireplace rank the highest. With Vrbo vacation rentals, there are options to suit your style and taste, whether you're taking a trip with your partner, your friends or even pets.

Are there large group vacation rentals in Leeward Settlement?

Leeward Settlement has 60 vacation properties that can fit 10 or more people. These properties come with enough space to share good times with your favorite people.

Are there vacation rentals in Leeward Settlement that welcome kids?

With 150 family-friendly vacation homes to pick from in Leeward Settlement, now is a superb time to introduce your children to the thrills of travel. Check our "Properties good for families" filter box to browse stays loaded with amenities ideal for traveling families, like multiple bedrooms, backyards, entertainment areas and bunk beds.

What are the top attractions for families in Leeward Settlement?

Keep the kids busy at these awesome family-friendly attractions in Leeward Settlement:

  • Grace Bay Beach
  • Turtle Cove
  • Providenciales Beaches

Are there one-bedroom vacation rentals in Leeward Settlement?

Leeward Settlement has 20 one-bedroom rentals available. Often located in prime spots due to their smaller size, a one-bedroom property is great if you're traveling with a buddy or your partner. And with plenty of home comforts like laundry facilities and more privacy than a standard hotel, you'll be able to kick back while enjoying this fabulous destination.

Can I find two-bedroom vacation rentals in Leeward Settlement?

Gather your family and experience complete comfort and privacy in one of the 18 two-bedroom vacation properties Leeward Settlement has to offer.

Are there vacation rentals with WiFi in Leeward Settlement?

You'll find 64 vacation rentals with WiFi in Leeward Settlement. If you'd like to disconnect from daily life on your trip, but still want to be connected to the internet, these properties are just what you need. Narrow your search by applying the WiFi filter on Vrbo.

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