10354+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. South Carolina
  3. Hilton Head
  4. Hilton Head Island

Hilton Head Island pickleball Stays, Resort Rentals, & Homes

About Hilton Head Island Vacation Rentals

Discover over 10354 amazing vacation rental options in Hilton Head Island 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 Hilton Head Island.

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 1231.39 ft², with prices averaging US $441 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 Hilton Head Island.

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Top Pickleball-Ready Accommodation Types in Hilton Head Island

Type Count
Vacation Homes 3439
Villas 2788
Holiday Apartments 609
Cottages 26

Use these Quick Filters to Find a Vacation Rental in Hilton Head Island

★ 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 Hilton Head Island with PickleTrip™.

Weather in Hilton Head Island, SC

View the weather forecast for Hilton Head Island before booking your Hilton Head Island Vacation Rentals to confirm your best time to go.

December - February
High 74°F       Low 43°F
March - May
High 87°F       Low 48°F
June - August
High 92°F       Low 72°F
September - November
High 89°F       Low 48°F

Top Attractions Around Hilton Head Island, SC

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


Coligny Beach
South Forest Beach
Harbour Town Lighthouse
Coligny Plaza
Hilton Head Island Beaches
Sea Pines Forest Preserve
Palmetto Dunes Club
Harbour Town Golf Links
Folly Field Beach Park
The Sandbox
Shelter Cove Harbour
Port Royal Golf Club
Palmetto Hall Plantation Club
Singleton Beach
Golden Bear Golf Club
Driessen Beach Park
Oyster Reef Golf Club
Ocean Course at The Sea Pines Resort
Country Club of Hilton Head
Robert Trent Jones Course

Other Places to Stay in Hilton Head Island, SC


Hilton Head 9,379 Properties
Sea Pines 2,839 Properties
Folly Field 1,326 Properties
Shipyard Plantation 967 Properties
North Forest Beach 905 Properties
South Beach 381 Properties
Harbour Town 280 Properties
Oceanside 170 Properties
Heritage Woods 151 Properties
Beach Lagoon 97 Properties
Shelter Cove 74 Properties
Lawton Woods 68 Properties

Frequently Asked Questions About Hilton Head Island?

What are the top vacation rentals, resorts, and hotels in Hilton Head Island 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 Hilton Head Island. 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 Hilton Head Island!

How many pickleball-ready properties have private pools in Hilton Head Island?

Discover 1581 accommodations with private or nearby pickleball courts in Hilton Head Island. Some of the best destinations to stay and play pickleball are:

Which vacation rentals, resorts, or hotels in Hilton Head Island is best for families looking for a pickleball-getaway?

Looking for a fun and active getaway with pickleball courts in Hilton Head Island? 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 Hilton Head Island?

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 10354 properties listed in Hilton Head Island 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.

Nearby Neighborhood (16) 
Neighborhood Property Count
Sea Pines Vacation Rentals in Hilton Head Island, South Carolina 2839
North Forest Beach Vacation Rentals in Hilton Head Island, South Carolina 905
South Beach Vacation Rentals in Hilton Head Island, South Carolina 381
Harbour Town Vacation Rentals in Hilton Head Island, South Carolina 280
Oceanside Vacation Rentals in Hilton Head Island, South Carolina 170
Heritage Woods Vacation Rentals in Hilton Head Island, South Carolina 151
Beach Lagoon Vacation Rentals in Hilton Head Island, South Carolina 97
Lawton Woods Vacation Rentals in Hilton Head Island, South Carolina 68
Night Heron Vacation Rentals in Hilton Head Island, South Carolina 56
The Cottages Vacation Rentals in Hilton Head Island, South Carolina 8491
Baynard Oaks Vacation Rentals in Hilton Head Island, South Carolina 2396
Moss Creek Vacation Rentals in Hilton Head Island, South Carolina 69
Spanish Wells Vacation Rentals in Hilton Head Island, South Carolina 2887
Bald Eagle West Vacation Rentals in Hilton Head Island, South Carolina 2766
Calibogue Cay Vacation Rentals in Hilton Head Island, South Carolina 6317
Colleton River Plantation Vacation Rentals in Hilton Head Island, South Carolina 265

People Also Ask

There are 10354 Hilton Head Island, SC Vacation Rentals

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