Osceola pickleball Stays, Resort Rentals, & Homes
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Luxury Places to Stay in Osceola
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Top-Rated Villas with a Pool in Osceola
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Pet-Friendly Villas in Osceola
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Large Private Villas in Osceola
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Osceola Villas, Airbnb and Holiday Homes Under $200
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Instantly Bookable Villa Rentals in Osceola
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Book a Last Minute Place to Stay in Osceola
About Osceola Vacation Rentals
Discover over 58 amazing vacation rental options in Osceola 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 Osceola.
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 559.51 ft², with prices averaging US $180 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 Osceola.
Top Pickleball-Ready Accommodation Types in Osceola
| Type | Count |
|---|---|
| Vacation Homes | 29 |
| Holiday Apartments | 8 |
Use these Quick Filters to Find a Vacation Rental in Osceola
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★ 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 Osceola with PickleTrip™.
Weather in Osceola, MO
View the weather forecast for Osceola before booking your Osceola Vacation Rentals to confirm your best time to go.
Top Attractions Around Osceola, MO
PickleTrip offers a large selection of top attractions around Osceola . Research things to do on your vacation before you visit Osceola.
Other Places to Stay in Osceola, MO
Frequently Asked Questions About Osceola?
What are the top vacation rentals, resorts, and hotels in Osceola 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 Osceola. 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 Osceola!
- Newly Renovated Super Clean Cabin on Truman Lake Warsaw, Clinton, Bucksaw.
- The Chestnut on the Square Historic Loft A
- Johnnie Sue’s in Wheatland. 3 bed, 2 bath home, plenty of parking, sleeps 10.
- T's Fish Camp-Crappie Are Biting—Sleeps up to Six
- Postcard Cabins Ozark Highlands, Outdoor Collection by Marriott Bonvoy
- Chestnut on the square, unit B
- Secluded Hunting & Fishing cabin in the Woods - Osceola, MO
- Quiet home near Berry Bend boat ramp with carports
- Farm house close to lake and public hunting land but yet far away for privacy !
- Quaint cabin with AC in Weaubleau
Which vacation rentals, resorts, or hotels in Osceola is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Osceola? 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.
- Spectacular view on the bluff of Truman Lake
- Truman Lake Cabin - Secluded and private
- Cozy Camper at Truman Lake
How many PickleTrip vacation rentals or resorts are available in Osceola?
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 58 properties listed in Osceola 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.
