153+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. South Carolina
  3. Hilton Head
  4. Windmill Harbor

Windmill Harbor pickleball Stays, Resort Rentals, & Homes

About Windmill Harbor Vacation Rentals

Discover over 153 amazing vacation rental options in Windmill Harbor 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 Windmill Harbor.

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 719.25 ft², with prices averaging US $387 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 Windmill Harbor.

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Top Pickleball-Ready Accommodation Types in Windmill Harbor

Type Count
Vacation Homes 61
Villas 9
Holiday Apartments 8
Cottages 3

Use these Quick Filters to Find a Vacation Rental in Windmill Harbor

★ 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 Windmill Harbor with PickleTrip™.

Weather in Windmill Harbor, SC

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

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Windmill Harbor, SC

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


Marine Corps Recruit Depot Parris Island
Coligny Beach
Tybee Island Beach
South Forest Beach
Harbour Town Lighthouse
Coligny Plaza
Tybee Island Light Station and Museum
Bay Street
Hilton Head Island Beaches
Sea Pines Forest Preserve
Palmetto Dunes Club
Harbour Town Golf Links
Tybee Island Fishing Pier and Pavilion
North Beach
Folly Field Beach Park
The Sandbox
Parris Island Museum
Shelter Cove Harbour
Wilmington Island Club
Marine Corps Air Station Beaufort

Frequently Asked Questions About Windmill Harbor?

What are the top vacation rentals, resorts, and hotels in Windmill Harbor 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 Windmill Harbor. 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 Windmill Harbor!

How many pickleball-ready properties have private pools in Windmill Harbor?

Discover 8 accommodations with private or nearby pickleball courts in Windmill Harbor. Some of the best destinations to stay and play pickleball are:

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

Looking for a fun and active getaway with pickleball courts in Windmill Harbor? 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 Windmill Harbor?

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 153 properties listed in Windmill Harbor 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.


People Also Ask

There are 153 Windmill Harbor, SC Vacation Rentals

Recently Booked Vacation Rentals in Windmill Harbor