559+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. Italy
  2. Tuscany
  3. Gaiole in Chianti

Gaiole in Chianti pickleball Stays, Resort Rentals, & Homes

About Gaiole in Chianti Vacation Rentals

Discover over 559 amazing vacation rental options in Gaiole in Chianti 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 Gaiole in Chianti.

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 1443.1 ft², with prices averaging US $535 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 Gaiole in Chianti.

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Top Pickleball-Ready Accommodation Types in Gaiole in Chianti

Type Count
Villas 204
Holiday Apartments 175
Vacation Homes 141
Cottages 2

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

★ 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 Gaiole in Chianti with PickleTrip™.

Top Attractions Around Gaiole in Chianti, IT

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


Castle of Brolio
Meleto Castle
Cantalici Winery
Badia a Coltibuono
Medieval Tower of Barbischio
Gaiole in Chianti Stadium
Church of San Sigismondo
PoggioBrandani
Piazza del Campo
Siena Cathedral
The Mall Luxury Outlet
Santa Maria alle Scotte Polyclinic
University of Siena
Piazza della Cisterna
Arezzo Equestrian Centre
San Donato Hospital
San Giovanni Terme Rapolano
Banca Monte dei Paschi di Siena
Centro Chirurgico Toscano
Monteriggioni Castle

Other Places to Stay in Gaiole in Chianti, IT


Vertine 680 Properties
PoggioBrandani 602 Properties
Lecchi in Chianti 591 Properties
Montegrossi 564 Properties
Monti 447 Properties
Monti di Sotto 432 Properties
San Vincenti 374 Properties
Nusenna 371 Properties
Starda 338 Properties
Rietine 97 Properties
Badia Coltibuono 91 Properties
San Sano 31 Properties

Frequently Asked Questions About Gaiole in Chianti?

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

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

Discover 129 accommodations with private or nearby pickleball courts in Gaiole in Chianti. Some of the best destinations to stay and play pickleball are:

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

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

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 559 properties listed in Gaiole in Chianti 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.


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There are 559 Gaiole in Chianti, IT Vacation Rentals

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