159+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  4. Montemassi

Montemassi pickleball Stays, Resort Rentals, & Homes

About Montemassi Vacation Rentals

Discover over 159 amazing vacation rental options in Montemassi 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 Montemassi.

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 790.22 ft², with prices averaging US $225 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 Montemassi.

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Top Pickleball-Ready Accommodation Types in Montemassi

Type Count
Vacation Homes 73
Holiday Apartments 37
Villas 22

Use these Quick Filters to Find a Vacation Rental in Montemassi

★ 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 Montemassi with PickleTrip™.

Top Attractions Around Montemassi, IT

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


Podere Ristella Vineyards and Winery
Cala Violina
Abbazia di San Galgano
Castello Banfi
Terme Petriolo
Scarlino Marina
State Natural Reserve Tomboli Follonica
Natural Reserve Diaccia Botrona
Val di Merse
Baluardo a tre punte
Cala Martina
Castello di Montepescini
Hospital of Mercy - Emergency Room
Abbey of San Lorenzo al Lanzo
Grosseto Cathedral
Vetulonia Ruins
Church of Saints Stephen and Lawrence
Piscina Il Giunco
Le Biancane
Monumento al Milite Ignoto

Other Places to Stay in Montemassi, IT


Podere Ristella Vineyards and Winery 241 Properties

Frequently Asked Questions About Montemassi?

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

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

Discover 6 accommodations with private or nearby pickleball courts in Montemassi. Some of the best destinations to stay and play pickleball are:

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

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

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 159 properties listed in Montemassi 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 159 Montemassi, IT Vacation Rentals

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