560+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Philipsburg pickleball Stays, Resort Rentals, & Homes

About Philipsburg Vacation Rentals

Discover over 560 amazing vacation rental options in Philipsburg 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 Philipsburg.

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 967.21 ft², with prices averaging US $631 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 Philipsburg.

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Top Pickleball-Ready Accommodation Types in Philipsburg

Type Count
Holiday Apartments 189
Villas 166
Vacation Homes 96

Use these Quick Filters to Find a Vacation Rental in Philipsburg

★ 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 Philipsburg with PickleTrip™.

Weather in Philipsburg, SX

View the weather forecast for Philipsburg before booking your Philipsburg 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 Philipsburg, SX

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


Great Bay Beach
Guana Bay Beach
University of St. Martin
Fort Amsterdam
Philipsburg Courthouse
Little Bay Beach
Sint Maarten Park
Cyrus Wathey Square
Museum of Sint Maarten
Guana Bay
Yoda Guy Movie Exhibit
Maho Beach
Mullet Bay Beach
American University of the Caribbean
Kim Sha Beach
Cupecoy Beach
Dawn Beach
Simpson Bay Beach
Starz City Casino

Other Places to Stay in Philipsburg, SX


Sint Maarten 1,633 Properties
Great Bay Beach 1,065 Properties
Madame's Estate 1,054 Properties
Philipsburg Boardwalk 1,027 Properties
Vineyard 780 Properties
Upper Prince's Quarter 354 Properties
Little Bay 128 Properties
Maho 88 Properties
Indigo Bay 57 Properties
Cay Bay Hill 57 Properties
Belair 32 Properties
Point Blanche 30 Properties

Frequently Asked Questions About Philipsburg?

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

How many pickleball-ready properties have private pools in Philipsburg?

Discover 119 accommodations with private or nearby pickleball courts in Philipsburg. Some of the best destinations to stay and play pickleball are:

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

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

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 560 properties listed in Philipsburg 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 (9) 
Neighborhood Property Count
Indigo Bay Vacation Rentals in Philipsburg 57
Belair Vacation Rentals in Philipsburg 32
Point Blanche Vacation Rentals in Philipsburg 30
Vineyard Vacation Rentals in Philipsburg 780
Madame's Estate Vacation Rentals in Philipsburg 1054
Red Pond Estates Vacation Rentals in Philipsburg 671
Sucker Garden Vacation Rentals in Philipsburg 796
Fort William Vacation Rentals in Philipsburg 1015
Hope Estate Vacation Rentals in Philipsburg 777

People Also Ask

There are 560 Philipsburg, SX Vacation Rentals

Recently Booked Vacation Rentals in Philipsburg