434+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. U.S. Virgin Islands
  2. St. John
  3. Estate Chocolate Hole and Great Cruz Bay

Estate Chocolate Hole and Great Cruz Bay pickleball Stays, Resort Rentals, & Homes

About Estate Chocolate Hole and Great Cruz Bay Vacation Rentals

Discover over 434 amazing vacation rental options in Estate Chocolate Hole and Great Cruz Bay 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 Estate Chocolate Hole and Great Cruz Bay.

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 953.45 ft², with prices averaging $1,469 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 Estate Chocolate Hole and Great Cruz Bay.

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Top Pickleball-Ready Accommodation Types in Estate Chocolate Hole and Great Cruz Bay

Type Count
Villas 158
Vacation Homes 36
Holiday Apartments 23
Cottages 8

Use these Quick Filters to Find a Vacation Rental in Estate Chocolate Hole and Great Cruz Bay

★ 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 Estate Chocolate Hole and Great Cruz Bay with PickleTrip™.

Top Attractions Around Estate Chocolate Hole and Great Cruz Bay, VI

PickleTrip offers a large selection of top attractions around Estate Chocolate Hole and Great Cruz Bay . Research things to do on your vacation before you visit Estate Chocolate Hole and Great Cruz Bay.


Sapphire Beach
Trunk Bay
Coki Beach
Honeymoon Beach
Virgin Islands National Park
Bolongo Bay
Magens Bay Beach
Blackbeard's Castle
Cinnamon Bay Beach
Coral World Ocean Park
Caneel Bay Beach
Maho Beach
St. John Spice
Secret Harbour Beach
Morningstar Beach
St. Thomas Synagogue
Lindbergh Bay
Caribbean Genealogy Library
Yacht Haven Grande Marina

Other Places to Stay in Estate Chocolate Hole and Great Cruz Bay, VI


Cruz Bay 784 Properties
Monte 412 Properties

Frequently Asked Questions About Estate Chocolate Hole and Great Cruz Bay?

What are the top vacation rentals, resorts, and hotels in Estate Chocolate Hole and Great Cruz Bay 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 Estate Chocolate Hole and Great Cruz Bay. 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 Estate Chocolate Hole and Great Cruz Bay!

How many pickleball-ready properties have private pools in Estate Chocolate Hole and Great Cruz Bay?

Discover 66 accommodations with private or nearby pickleball courts in Estate Chocolate Hole and Great Cruz Bay. Some of the best destinations to stay and play pickleball are:

Which vacation rentals, resorts, or hotels in Estate Chocolate Hole and Great Cruz Bay is best for families looking for a pickleball-getaway?

Looking for a fun and active getaway with pickleball courts in ? 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 Estate Chocolate Hole and Great Cruz Bay?

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 434 properties listed in Estate Chocolate Hole and Great Cruz Bay 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 (1) 
Neighborhood Property Count
Contant Farms Vacation Rentals in St. John 33

People Also Ask

There are 434 Estate Chocolate Hole and Great Cruz Bay, VI Vacation Rentals

Recently Booked Vacation Rentals in Estate Chocolate Hole and Great Cruz Bay