595+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Bloomington pickleball Stays, Resort Rentals, & Homes

About Bloomington Vacation Rentals

Discover over 595 amazing vacation rental options in Bloomington 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 Bloomington.

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 800.22 ft², with prices averaging US $386 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 Bloomington.

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Top Pickleball-Ready Accommodation Types in Bloomington

Type Count
Vacation Homes 348
Holiday Apartments 110
Cottages 10
Villas 4

Use these Quick Filters to Find a Vacation Rental in Bloomington

★ 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 Bloomington with PickleTrip™.

Weather in Bloomington, IN

View the weather forecast for Bloomington before booking your Bloomington 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 Bloomington, IN

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


Indiana University Bloomington
Lake Monroe
Assembly Hall
Oliver Winery
Indiana University Auditorium
Bloomington Speedway
Memorial Stadium
Tibetan Mongolian Buddhist Cultural Center
Jump-N-Joey's
Bloomington Monroe County Convention Center
Lawrence County Museum of History
Monroe County Courthouse
Bluespring Caverns
Cascades Golf Course
IU Opera and Ballet Theater
Cascades Park
Otis Park Golf Course
Bill Armstrong Stadium
Indiana University Golf Course

Other Places to Stay in Bloomington, IN


Indiana University Bloomington 407 Properties
Indiana University Auditorium 403 Properties
IU Opera and Ballet Theater 401 Properties
Bloomington Monroe County Convention Center 391 Properties
Monroe County Courthouse 390 Properties
Monroe County 364 Properties
Ellettsville 134 Properties
Spencer 47 Properties
Unionville 38 Properties
Shawswick 34 Properties
Bedford 33 Properties
Lawrence County 24 Properties

Frequently Asked Questions About Bloomington?

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

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

Discover 20 accommodations with private or nearby pickleball courts in Bloomington. Some of the best destinations to stay and play pickleball are:

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

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

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 595 properties listed in Bloomington in 2026, 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 595 Bloomington, IN Vacation Rentals

Recently Booked Vacation Rentals in Bloomington