204+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Tortola
  3. Road Town
  4. Pleasent Valley

Pleasent Valley pickleball Stays, Resort Rentals, & Homes

About Pleasent Valley Vacation Rentals

Discover over 204 amazing vacation rental options in Pleasent Valley 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 Pleasent Valley.

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 781.17 ft², with prices averaging $690 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 Pleasent Valley.

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Top Pickleball-Ready Accommodation Types in Pleasent Valley

Type Count
Villas 67
Holiday Apartments 57
Vacation Homes 24
Cottages 6

Use these Quick Filters to Find a Vacation Rental in Pleasent Valley

★ 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 Pleasent Valley with PickleTrip™.

Top Attractions Around Pleasent Valley, VG

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


The Baths
Tortola Cruise Ship Port
Little Dix Bay Beach
Cane Garden Bay Beach
White Bay Beach
Leverick Bay Marina
Trunk Bay Beach
Trellis Bay Beach
Smuggler's Cove Beach
Savannah Beach
Nanny Cay
Virgin Gorda Harbor
Mahoe Bay Beach
Long Bay Beach
Soper's Hole Marina
Long Bay Beach
Anegada Island
Hodge's Creek Marina
Cam Bay Beach

Frequently Asked Questions About Pleasent Valley?

What are the top vacation rentals, resorts, and hotels in Pleasent Valley 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 Pleasent Valley. 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 Pleasent Valley!

How many pickleball-ready properties have private pools in Pleasent Valley?

Discover 25 accommodations with private or nearby pickleball courts in Pleasent Valley. Some of the best destinations to stay and play pickleball are:

Which vacation rentals, resorts, or hotels in Pleasent Valley 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 Pleasent Valley?

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 204 properties listed in Pleasent Valley 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 204 Pleasent Valley, VG Vacation Rentals

Recently Booked Vacation Rentals in Pleasent Valley