81+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Pleasant Prairie pickleball Stays, Resort Rentals, & Homes

About Pleasant Prairie Vacation Rentals

Discover over 81 amazing vacation rental options in Pleasant Prairie 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 Pleasant Prairie.

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 479.49 ft², with prices averaging US $461 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 Pleasant Prairie.

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Top Pickleball-Ready Accommodation Types in Pleasant Prairie

Type Count
Vacation Homes 42
Holiday Apartments 6
Villas 1

Use these Quick Filters to Find a Vacation Rental in Pleasant Prairie

★ 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 Pleasant Prairie with PickleTrip™.

Weather in Pleasant Prairie, WI

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

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Pleasant Prairie, WI

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


Pleasant Prairie RecPlex
Pleasant Prairie Premium Outlets
Jelly Belly Center
Keno Drive-In
Naval Base Great Lakes
Six Flags Great America
Gurnee Mills
Wilmot Mountain
Illinois Beach State Park
Volo Auto Museum
Genesee Theater
Lake Forest College
Northwestern Lake Forest Hospital
Carthage College
Lake County Fairgrounds
College of Lake County
Waukegan Harbor
Racine Zoological Gardens
Jump America
Kenosha Public Museum

Other Places to Stay in Pleasant Prairie, WI


Jelly Belly Center 98 Properties
Pleasant Prairie RecPlex 88 Properties
Pleasant Prairie Premium Outlets 71 Properties
Keno Drive-In 59 Properties

Frequently Asked Questions About Pleasant Prairie?

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

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

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

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 81 properties listed in Pleasant Prairie 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 81 Pleasant Prairie, WI Vacation Rentals

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