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

Montegrossi pickleball Stays, Resort Rentals, & Homes

About Montegrossi Vacation Rentals

Discover over 365 amazing vacation rental options in Montegrossi 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 Montegrossi.

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 1377.54 ft², with prices averaging US $542 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 Montegrossi.

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Top Pickleball-Ready Accommodation Types in Montegrossi

Type Count
Villas 141
Holiday Apartments 95
Vacation Homes 91
Cottages 8

Use these Quick Filters to Find a Vacation Rental in Montegrossi

★ 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 Montegrossi with PickleTrip™.

Top Attractions Around Montegrossi, IT

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


Piazza del Campo
Siena Cathedral
The Mall Luxury Outlet
Santa Maria alle Scotte Polyclinic
University of Siena
Arezzo Equestrian Centre
San Giovanni Terme Rapolano
Banca Monte dei Paschi di Siena
Monteriggioni Castle
Cantina Antinori
Valdarno
Val di Chiana
Castle of Brolio
Castello di Radda Winery
Terme Antica Querciolaia
Meleto Castle
Villa a Sesta Polo Club
Fortezza Medicea
Porta Camollia
Ruffino - Tenuta di Poggio Casciano

Frequently Asked Questions About Montegrossi?

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

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

Discover 85 accommodations with private or nearby pickleball courts in Montegrossi. Some of the best destinations to stay and play pickleball are:

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

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

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 365 properties listed in Montegrossi 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 365 Montegrossi, IT Vacation Rentals

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