2122+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. U.S. Virgin Islands
  2. South Side

South Side pickleball Stays, Resort Rentals, & Homes

About South Side Vacation Rentals

Discover over 2122 amazing vacation rental options in South Side 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 South Side.

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 549.83 ft², with prices averaging US $530 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 South Side.

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Top Pickleball-Ready Accommodation Types in South Side

Type Count
Holiday Apartments 457
Villas 235
Vacation Homes 185
Cottages 11

Use these Quick Filters to Find a Vacation Rental in South Side

★ 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 South Side with PickleTrip™.

Frequently Asked Questions About South Side?

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

How many pickleball-ready properties have private pools in South Side?

Discover 221 accommodations with private or nearby pickleball courts in South Side. Some of the best destinations to stay and play pickleball are:

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

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

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 2122 properties listed in South Side 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.


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There are 2122 South Side, VI Vacation Rentals

Recently Booked Vacation Rentals in South Side