366+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. Turks and Caicos
  2. Providenciales
  3. Leeward Settlement

Leeward Settlement pickleball Stays, Resort Rentals, & Homes

About Leeward Settlement Vacation Rentals

Discover over 366 amazing vacation rental options in Leeward Settlement with pickleball courts or nearby facilities. From resorts to hotels, villas to condos, PickleTrip connects you with a vast selection of pickleball-ready amenities at great prices, providing you with the perfect spot to base your next pickleball vacation. Stay and Play pickleball When You Travel and uncover great stays in Leeward Settlement.

Find exclusive last-minute deals on vacation rentals, resorts, and hotels with private courts and nearby facilities with PickleTrip™, whether you're traveling solo or with a group. Our platform offers a variety of stay options, from vacation rentals to Airbnb-style properties, all with private pickleball courts or nearby facilities. Compare options from multiple suppliers with a single click to find the perfect stay that fits your budget and style. Places to stay near pickleball courts are an average of 3652.48 ft², with prices averaging US $3,369 per night.

With PickleTrip™, you can easily search for and book your next pickleball vacation rental with courts or nearby facilities. Our platform connects you with the ideal holiday rental to create a lifetime of travel memories. Prices listed are often discounted versus rack rates, so you can secure your perfect place to stay today and get ready to play pickleball in Leeward Settlement.

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Top Pickleball-Ready Accommodation Types in Leeward Settlement

Type Count
Villas 218
Vacation Homes 70
Holiday Apartments 27
Cottages 10

Use these Quick Filters to Find a Vacation Rental in Leeward Settlement

★ Pro Tip: PickleTrip™ is a travel platform, connecting avid pickleball players and enthusiasts with a variety of vacation rentals, resorts, and hotels featuring private pickleball courts or nearby facilities. We curate a vast selection of properties from trusted sources, providing you with unbeatable options and pricing to find the perfect pickleball getaway. Experience unforgettable pickleball matches in Leeward Settlement with PickleTrip™.

Weather in Leeward Settlement, TC

View the weather forecast for Leeward Settlement before booking your Leeward Settlement Vacation Rentals to confirm your best time to go.

December - February
High 84°F       Low 71°F
March - May
High 86°F       Low 73°F
June - August
High 91°F       Low 80°F
September - November
High 89°F       Low 75°F

Top Attractions Around Leeward Settlement, TC

PickleTrip offers a large selection of top attractions around Leeward Settlement . Research things to do on your vacation before you visit Leeward Settlement.


Leeward Beach
Provo Conch Farm
Turtle Cove
Grace Bay Beach
Long Bay Beach
Sapodilla Bay
Providenciales Beaches
Pelican Beach
Taylor Bay Beach
Chalk Sound
The Regent Village Shopping Mall
Coral Gardens Reef
Salt Mills Plaza
Chalk Sound National Park
Pirate's Cove
Northwest Point National Park
Little Water Cay
Parrot Cay Beach
Three Mary Cays
The Hole

Other Places to Stay in Leeward Settlement, TC


Leeward Beach 1,102 Properties
Provo Conch Farm 948 Properties

Frequently Asked Questions About Leeward Settlement?

What are the top vacation rentals, resorts, and hotels in Leeward Settlement with Courts?

Experience the ultimate pickleball vacation with PickleTrip™. We offer a variety of premium rental properties, resorts, and hotels with private pickleball courts or nearby facilities in Leeward Settlement. Whether you're a beginner or a seasoned player, we have the perfect destination for you to stay and play. Book now and discover the best pickleball vacation spots in Leeward Settlement!

How many pickleball-ready properties have private pools in Leeward Settlement?

Discover 155 accommodations with private or nearby pickleball courts in Leeward Settlement. Some of the best destinations to stay and play pickleball are:

Which vacation rentals, resorts, or hotels in Leeward Settlement is best for families looking for a pickleball-getaway?

Looking for a fun and active getaway with pickleball courts in Leeward Settlement? With PickleTrip™, you'll have access to a wide selection of top-rated properties that offer private pickleball courts or nearby facilities. Make the most of you getaway and ace your A-game while you travel.

How many PickleTrip vacation rentals or resorts are available in Leeward Settlement?

PickleTrip™ offers a diverse selection of properties with private pickleball courts or nearby facilities to enhance your pickleball experience on your next trip. With a combination of established great stays and new options in top locations, PickleTrip™ has over 366 properties listed in Leeward Settlement in 2025, and the number only continues to grow. By consolidating listings from various providers, PickleTrip™ brings you the best luxury stays for a sporty, professional, and fun travel experience.


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There are 366 Leeward Settlement, TC Vacation Rentals

Recently Booked Vacation Rentals in Leeward Settlement