123+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. British Virgin Islands
  2. Virgin Gorda
  3. Head of The Bay

Head of The Bay pickleball Stays, Resort Rentals, & Homes

About Head of The Bay Vacation Rentals

Discover over 123 amazing vacation rental options in Head of The 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 Head of The 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 2575.94 ft², with prices averaging US $1,305 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 Head of The Bay.

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Top Pickleball-Ready Accommodation Types in Head of The Bay

Type Count
Villas 106
Holiday Apartments 7
Vacation Homes 5

Use these Quick Filters to Find a Vacation Rental in Head of The 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 Head of The Bay with PickleTrip™.

Weather in Head of The Bay, VG

View the weather forecast for Head of The Bay before booking your Head of The Bay Vacation Rentals to confirm your best time to go.

December - February
High 82°F       Low 72°F
March - May
High 84°F       Low 72°F
June - August
High 86°F       Low 75°F
September - November
High 86°F       Low 74°F

Top Attractions Around Head of The Bay, VG

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


The Baths
Tortola Cruise Ship Port
Little Dix Bay Beach
Cane Garden Bay Beach
Oil Nut Bay Beach
Leverick Bay Marina
Trunk Bay Beach
Trellis Bay Beach
Necker Island
Smuggler's Cove Beach
Savannah Beach
Nanny Cay
Virgin Gorda Harbor
Bitter End Gardens
Mahoe Bay Beach
Long Bay Beach
Soper's Hole Marina
Long Bay Beach
Anegada Island

Frequently Asked Questions About Head of The Bay?

What are the top vacation rentals, resorts, and hotels in Head of The 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 Head of The 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 Head of The Bay!

How many pickleball-ready properties have private pools in Head of The Bay?

Discover 40 accommodations with private or nearby pickleball courts in Head of The Bay. Some of the best destinations to stay and play pickleball are:

Which vacation rentals, resorts, or hotels in Head of The Bay is best for families looking for a pickleball-getaway?

Looking for a fun and active getaway with pickleball courts in Head of The Bay? 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 Head of The 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 123 properties listed in Head of The 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.


People Also Ask

There are 123 Head of The Bay, VG Vacation Rentals

Recently Booked Vacation Rentals in Head of The Bay