951+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. Sint Maarten
  2. Lower Prince's Quarter
  3. Middle Region

Middle Region pickleball Stays, Resort Rentals, & Homes

About Middle Region Vacation Rentals

Discover over 951 amazing vacation rental options in Middle Region 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 Middle Region.

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 1045.97 ft², with prices averaging $637 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 Middle Region.

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Top Pickleball-Ready Accommodation Types in Middle Region

Type Count
Villas 373
Holiday Apartments 229
Vacation Homes 123
Cottages 3

Use these Quick Filters to Find a Vacation Rental in Middle Region

★ 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 Middle Region with PickleTrip™.

Weather in Middle Region, SX

View the weather forecast for Middle Region before booking your Middle Region 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

Frequently Asked Questions About Middle Region?

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

How many pickleball-ready properties have private pools in Middle Region?

Discover 313 accommodations with private or nearby pickleball courts in Middle Region. Some of the best destinations to stay and play pickleball are:

Which vacation rentals, resorts, or hotels in Middle Region 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 Middle Region?

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 951 properties listed in Middle Region 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 (2) 
Neighborhood Property Count
Madame's Estate Vacation Rentals in Lower Prince's Quarter 1054
Sucker Garden Vacation Rentals in Lower Prince's Quarter 796

People Also Ask

There are 951 Middle Region, SX Vacation Rentals

Recently Booked Vacation Rentals in Middle Region