173+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Osage pickleball Stays, Resort Rentals, & Homes

About Osage Vacation Rentals

Discover over 173 amazing vacation rental options in Osage 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 Osage.

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 411.12 ft², with prices averaging US $177 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 Osage.

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Top Pickleball-Ready Accommodation Types in Osage

Type Count
Vacation Homes 79
Holiday Apartments 19
Cottages 7
Villas 2

Use these Quick Filters to Find a Vacation Rental in Osage

★ 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 Osage with PickleTrip™.

Weather in Osage, IA

View the weather forecast for Osage before booking your Osage 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 Osage, IA

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


Mitchell County Courthouse
Sunny Brae Golf and Country Club
Osage City Park
Mitchell County Regional Health Center
Diamond Jo Casino
Paramount Theatre
The Historic Park Inn Hotel and City National Bank
Riverland Community College - Austin Campus
Spam Museum
Carrie Chapman Catt Girlhood Home and Museum
Hormel Historic Home
Buddy Holly Crash Site
Fossil & Prairie Center
Jay C. Hormel Nature Center
Community Park
North West Park
Austin ArtWorks Center
Echoes of the Past
Music Man Square
Meredith Willson Boyhood Home

Other Places to Stay in Osage, IA


Mitchell 253 Properties
Mitchell County 136 Properties
New Haven 32 Properties
Sunny Brae Golf and Country Club 28 Properties
Osage City Park 27 Properties
Mitchell County Regional Health Center 26 Properties
Mitchell County Courthouse 26 Properties

Frequently Asked Questions About Osage?

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

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

Discover 6 accommodations with private or nearby pickleball courts in Osage. Some of the best destinations to stay and play pickleball are:

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

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

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 173 properties listed in Osage 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 173 Osage, IA Vacation Rentals

Recently Booked Vacation Rentals in Osage