11136+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. Italy
  2. Tuscany
  3. Chianti Region

Chianti Region pickleball Stays, Resort Rentals, & Homes

About Chianti Region Vacation Rentals

Discover over 11136 amazing vacation rental options in Chianti Region 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 Chianti Region.

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 1365.8 ft², with prices averaging US $424 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 Chianti Region.

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Top Pickleball-Ready Accommodation Types in Chianti Region

Type Count
Holiday Apartments 3493
Vacation Homes 3466
Villas 2722
Cottages 124

Use these Quick Filters to Find a Vacation Rental in Chianti Region

★ 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 Chianti Region with PickleTrip™.

Weather in Chianti Region, IT

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

December - February
High 60°F       Low 26°F
March - May
High 73°F       Low 31°F
June - August
High 93°F       Low 54°F
September - November
High 76°F       Low 42°F

Top Attractions Around Chianti Region, IT

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


Cantina Antinori
Valdarno
Castle of Brolio
Castello di Radda Winery
Meleto Castle
Villa a Sesta Polo Club
Isole e Olena Winery
Castello della Paneretta
Il Molino di Grace Winery
Castello d'Albola
Tuscany MTB Guide
Montegufoni Castle
Casa del Boccaccio
Castello Sonnino
Santa Lucia al Borghetto Church
Buondonno Winery
Le Miccine
Cantalici Winery
Borgo di Vescine - Tenute di Castelvecchi
Colle di Val d'Elsa Cathedral

Other Places to Stay in Chianti Region, IT


Tuscany 78,334 Properties
Val d'Elsa 6,208 Properties
Colle di Val d'Elsa 4,488 Properties
Valdarno 2,175 Properties
Greve in Chianti 885 Properties
Barberino Tavarnelle 683 Properties
Gaiole in Chianti 511 Properties
Bucine 482 Properties
Barberino Val d'Elsa 463 Properties
Castellina in Chianti 421 Properties
Montespertoli 413 Properties
San Casciano in Val di Pesa 410 Properties

Frequently Asked Questions About Chianti Region?

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

How many pickleball-ready properties have private pools in Chianti Region?

Discover 2674 accommodations with private or nearby pickleball courts in Chianti Region. Some of the best destinations to stay and play pickleball are:

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

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

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 11136 properties listed in Chianti Region 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.

Nearby Neighborhood (2) 
Neighborhood Property Count
Certaldo Alto Vacation Rentals in Tuscany 33
Il Serraglio Vacation Rentals in Tuscany 591

People Also Ask

There are 11136 Chianti Region, IT Vacation Rentals

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