407+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Oyster Pond pickleball Stays, Resort Rentals, & Homes

About Oyster Pond Vacation Rentals

Discover over 407 amazing vacation rental options in Oyster Pond 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 Oyster Pond.

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 1183.93 ft², with prices averaging US $640 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 Oyster Pond.

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Top Pickleball-Ready Accommodation Types in Oyster Pond

Type Count
Villas 203
Holiday Apartments 47
Vacation Homes 25
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Oyster Pond

★ 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 Oyster Pond with PickleTrip™.

Weather in Oyster Pond, SX

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

December - February
High 85°F       Low 69°F
March - May
High 87°F       Low 72°F
June - August
High 89°F       Low 76°F
September - November
High 88°F       Low 73°F

Top Attractions Around Oyster Pond, SX

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


Dawn Beach
Oyster Bay Marina
Gibb's Bay Beach
Maho Beach
Mullet Bay Beach
American University of the Caribbean
Great Bay Beach
Guana Bay Beach
Kim Sha Beach
Cupecoy Beach
Simpson Bay Beach
University of St. Martin
Fort Amsterdam
Starz City Casino
Philipsburg Courthouse
Mullet Bay
Little Bay Beach
Sint Maarten Park
Flamingo Beach

Other Places to Stay in Oyster Pond, SX


Red Pond Estates 671 Properties
Gibb's Bay Beach 671 Properties
Tamarind Hill Estates 661 Properties
Dawn Beach 629 Properties
Oyster Bay Marina 550 Properties
Dawn Beach Estates 30 Properties

Frequently Asked Questions About Oyster Pond?

What are the top vacation rentals, resorts, and hotels in Oyster Pond 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 Oyster Pond. 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 Oyster Pond!

How many pickleball-ready properties have private pools in Oyster Pond?

Discover 156 accommodations with private or nearby pickleball courts in Oyster Pond. Some of the best destinations to stay and play pickleball are:

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

Looking for a fun and active getaway with pickleball courts in Oyster Pond? 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 Oyster Pond?

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 407 properties listed in Oyster Pond 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 (3) 
Neighborhood Property Count
Dawn Beach Estates Vacation Rentals in Oyster Pond 30
Tamarind Hill Estates Vacation Rentals in Oyster Pond 661
Red Pond Estates Vacation Rentals in Oyster Pond 671

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There are 407 Oyster Pond, SX Vacation Rentals

Recently Booked Vacation Rentals in Oyster Pond