Madison County pickleball Stays, Resort Rentals, & Homes
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Luxury Places to Stay in Madison County
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Top-Rated Villas with a Pool in Madison County
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Pet-Friendly Villas in Madison County
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Large Private Villas in Madison County
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Madison County Villas, Airbnb and Holiday Homes Under $200
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Book a Last Minute Place to Stay in Madison County
About Madison County Vacation Rentals
Discover over 27 amazing vacation rental options in Madison County 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 Madison County.
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 486.83 ft², with prices averaging US $189 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 Madison County.
Top Pickleball-Ready Accommodation Types in Madison County
| Type | Count |
|---|---|
| Vacation Homes | 11 |
| Cottages | 2 |
| Holiday Apartments | 1 |
Use these Quick Filters to Find a Vacation Rental in Madison County
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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 Madison County with PickleTrip™.
Weather in Madison County, FL
View the weather forecast for Madison County before booking your Madison County Vacation Rentals to confirm your best time to go.
Top Attractions Around Madison County, FL
PickleTrip offers a large selection of top attractions around Madison County . Research things to do on your vacation before you visit Madison County.
Other Places to Stay in Madison County, FL
Frequently Asked Questions About Madison County?
What are the top vacation rentals, resorts, and hotels in Madison County 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 Madison County. 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 Madison County!
- Peaceful cabin on the Cochee river w/4 acres land
- 'All Decked Out' Home on Cherry Lake w/Dock!
- The Haven of Peace in Madison County, FL
- Delightful 5th wheel w/ queen bed, patio deck, and high speed internet.
- Lakefront southern charm in beautiful quiet area
- Florida Waterfront Country Home, Fishing & Pet Friendly
- Family home on the lake. Please read the description!
- Cherry Lake Home Perfect for Family Gatherings. Close to Wild Adventures.
- Peaceful Country Getaway Pet Friendly and Cozy!
- Best Western Plus Madison
Which vacation rentals, resorts, or hotels in Madison County is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Madison County? 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 Madison County?
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 27 properties listed in Madison County 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.
