278+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. Italy
  2. Tuscany
  3. Pienza

Pienza pickleball Stays, Resort Rentals, & Homes

About Pienza Vacation Rentals

Discover over 278 amazing vacation rental options in Pienza 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 Pienza.

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 1309.9 ft², with prices averaging US $489 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 Pienza.

Show more
Show less

Top Pickleball-Ready Accommodation Types in Pienza

Type Count
Vacation Homes 97
Villas 70
Holiday Apartments 63
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Pienza

★ 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 Pienza with PickleTrip™.

Top Attractions Around Pienza, IT

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


Pienza Cathedral
Piazza Pio II
Palazzo Piccolomini
RI Crea RE
Enoteca Di Ghino
Pieve di CorsigNoneo
Artemisia Gallery
Art Studio di Adelina Quadri
Palazzo Vescovile
Palazzo Borgia
Museo Diocesano
Palazzo Comunale
Historic Centre of Pienza
Lake Trasimeno
Monte Amiata
Baths of San Filippo
Piscine Termali Theia
San Giovanni Terme Rapolano
Terme di Montepulciano Spa
Castello Banfi

Other Places to Stay in Pienza, IT


Art Studio di Adelina Quadri 494 Properties
Palazzo Vescovile 487 Properties
Palazzo Borgia 487 Properties
Museo Diocesano 487 Properties
Pienza Cathedral 487 Properties
Piazza Pio II 487 Properties
Palazzo Comunale 487 Properties
Palazzo Piccolomini 486 Properties
Historic Centre of Pienza 486 Properties
Artemisia Gallery 486 Properties
Enoteca Di Ghino 486 Properties
Monticchiello 37 Properties

Frequently Asked Questions About Pienza?

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

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

Discover 38 accommodations with private or nearby pickleball courts in Pienza. Some of the best destinations to stay and play pickleball are:

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

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

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 278 properties listed in Pienza 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 278 Pienza, IT Vacation Rentals

Recently Booked Vacation Rentals in Pienza