430+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. U.S. Virgin Islands
  2. St. Thomas
  3. Southside

Southside pickleball Stays, Resort Rentals, & Homes

About Southside Vacation Rentals

Discover over 430 amazing vacation rental options in Southside 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 Southside.

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 438.14 ft², with prices averaging US $651 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 Southside.

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Top Pickleball-Ready Accommodation Types in Southside

Type Count
Holiday Apartments 72
Villas 61
Vacation Homes 32
Cottages 2

Use these Quick Filters to Find a Vacation Rental in Southside

★ 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 Southside with PickleTrip™.

Weather in Southside, VI

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

December - February
High 84°F       Low 72°F
March - May
High 85°F       Low 72°F
June - August
High 88°F       Low 74°F
September - November
High 88°F       Low 73°F

Top Attractions Around Southside, VI

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


Caribbean Genealogy Library
Skyride to Paradise Point
Havensight Mall
Buck Island Turtle Cove
Mangrove Lagoon
Frenchman's Bay
The Butterfly Garden
Mango Tango Art Gallery
Sapphire Beach
Trunk Bay
Coki Beach
Honeymoon Beach
Virgin Islands National Park
Bolongo Bay
Magens Bay Beach
Blackbeard's Castle
Cinnamon Bay Beach
Coral World Ocean Park
Caneel Bay Beach
Maho Beach
St. John Spice
Secret Harbour Beach
Morningstar Beach
St. Thomas Synagogue
Lindbergh Bay
Yacht Haven Grande Marina
University of Virgin Islands
Fort Christian
Smith Bay Beach

Other Places to Stay in Southside, VI


Estate Bovoni 2,012 Properties
Mangrove Lagoon 1,933 Properties
Estate Charlotte Amalie 1,880 Properties
Estate Hoffman 1,614 Properties
Estate Bolongo 1,386 Properties
Havensight 1,073 Properties
Bellevue 1,030 Properties
Frenchman's Bay 303 Properties
South Coast 163 Properties
Estate Frenchman Bay 147 Properties
Green Cay Plantation 147 Properties
Estate Bakkero 146 Properties

Frequently Asked Questions About Southside?

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

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

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

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

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

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 430 properties listed in Southside 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.


People Also Ask

There are 430 Southside, VI Vacation Rentals

Recently Booked Vacation Rentals in Southside