Discover a selection of 1,000 vacation rentals in Leeward Settlement that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $160 per night, and houses and villas are popular options for a stay in Leeward Settlement. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Leeward Settlement
Destination guide

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.

Things to do

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.

Natural features

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.

How to get there

Transportation options to and around Leeward Settlement

Fly into Providenciales Intl. Airport (PLS), the closest airport, located 8.2 mi (13.2 km) from the city center.

How many vacation rentals are available around Leeward Settlement?

Our 2022 property listings offer a large selection of 929 vacation rentals around Leeward Settlement. From 589 house rentals to 403 villa rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses in Leeward Settlement?

Yes, of course. Vrbo has 589 Houses in Leeward Settlement. Our other popular types of vacation rentals in Leeward Settlement include:

  • Villas: 403 rentals available
  • Condos/Apartments: 286 rentals available
  • Cottages: 38 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Studios and more.

Can I find a vacation rental with pool in Leeward Settlement?

Yes, you can select your preferred vacation rental with pool among our 780 vacation rentals with pool available in Leeward Settlement. Please use our search bar to access the selection of vacation rentals available.