103+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Philipsburg
  3. Cay Bay Hill

Cay Bay Hill pickleball Stays, Resort Rentals, & Homes

About Cay Bay Hill Vacation Rentals

Discover over 103 amazing vacation rental options in Cay Bay Hill 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 Cay Bay Hill.

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 1257.88 ft², with prices averaging US $997 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 Cay Bay Hill.

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Top Pickleball-Ready Accommodation Types in Cay Bay Hill

Type Count
Villas 70
Holiday Apartments 20
Vacation Homes 9

Use these Quick Filters to Find a Vacation Rental in Cay Bay Hill

★ 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 Cay Bay Hill with PickleTrip™.

Weather in Cay Bay Hill, SX

View the weather forecast for Cay Bay Hill before booking your Cay Bay Hill 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 Cay Bay Hill, SX

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


Maho Beach
Mullet Bay Beach
American University of the Caribbean
Great Bay Beach
Guana Bay Beach
Kim Sha Beach
Cupecoy Beach
Dawn 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
Casino Royale
Dunes Casino

Other Places to Stay in Cay Bay Hill, SX


Indigo Bay 57 Properties

Frequently Asked Questions About Cay Bay Hill?

What are the top vacation rentals, resorts, and hotels in Cay Bay Hill 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 Cay Bay Hill. 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 Cay Bay Hill!

How many pickleball-ready properties have private pools in Cay Bay Hill?

Discover 22 accommodations with private or nearby pickleball courts in Cay Bay Hill. Some of the best destinations to stay and play pickleball are:

Which vacation rentals, resorts, or hotels in Cay Bay Hill is best for families looking for a pickleball-getaway?

Looking for a fun and active getaway with pickleball courts in Cay Bay Hill? 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 Cay Bay Hill?

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 103 properties listed in Cay Bay Hill 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
Indigo Bay Vacation Rentals in Philipsburg 57

People Also Ask

There are 103 Cay Bay Hill, SX Vacation Rentals

Recently Booked Vacation Rentals in Cay Bay Hill