114+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. U.S. Virgin Islands
  2. St. Croix Island
  3. Southwest

Southwest pickleball Stays, Resort Rentals, & Homes

About Southwest Vacation Rentals

Discover over 114 amazing vacation rental options in Southwest 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 Southwest.

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 432.09 ft², with prices averaging US $500 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 Southwest.

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Top Pickleball-Ready Accommodation Types in Southwest

Type Count
Vacation Homes 39
Holiday Apartments 27
Cottages 4
Villas 4

Use these Quick Filters to Find a Vacation Rental in Southwest

★ 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 Southwest with PickleTrip™.

Weather in Southwest, VI

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

December - February
High 85°F       Low 73°F
March - May
High 87°F       Low 73°F
June - August
High 89°F       Low 78°F
September - November
High 88°F       Low 76°F

Top Attractions Around Southwest, VI

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


Sandy Point
Carmbola Tide Pools
Estate Whim Museum
East Wall
Moravian Church
Carambola Golf Club
Anchor Wall
Reef Club Golf Course
West Wall
St. Croix Point Udall
St. Croix Government House
Buccaneer Golf Course
Frederiksted Pier
Christiansted National Historic Site
Cane Bay
Rainbow Beach
Sugar Beach
Buck Island Reef National Monument
Chenay Bay Beach
Cruzan Rum Factory
Casino at the Divi Carina Bay
Reef Beach
Old Danish Customs House
Old Danish School
Isaac Bay
Protestant Cay
Grape Tree Beach
St Paul's Episcopal Anglican Church
Buccaneer Beach

Other Places to Stay in Southwest, VI


Estate Whim Museum 97 Properties
Estate Carlton 1 North 95 Properties
Estate Cane 93 Properties
Carlton 90 Properties
West Wall 88 Properties
East Wall 88 Properties
Hannah's Rest 87 Properties
Estate Hannahs Rest 86 Properties
Estate Two Brothers 82 Properties
Estate Whites Bay 1 82 Properties
Estate Whim 46 Properties
Estate Enfield Green 33 Properties

Frequently Asked Questions About Southwest?

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

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

Discover 4 accommodations with private or nearby pickleball courts in Southwest. Some of the best destinations to stay and play pickleball are:

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

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

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 114 properties listed in Southwest 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 114 Southwest, VI Vacation Rentals

Recently Booked Vacation Rentals in Southwest