1460+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. Italy
  2. Tuscany
  3. Siena

Siena pickleball Stays, Resort Rentals, & Homes

About Siena Vacation Rentals

Discover over 1460 amazing vacation rental options in Siena 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 Siena.

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 708.33 ft², with prices averaging US $237 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 Siena.

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Top Pickleball-Ready Accommodation Types in Siena

Type Count
Holiday Apartments 945
Vacation Homes 206
Villas 75
Cottages 2

Use these Quick Filters to Find a Vacation Rental in Siena

★ 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 Siena with PickleTrip™.

Weather in Siena, IT

View the weather forecast for Siena before booking your Siena 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 94°F       Low 54°F
September - November
High 76°F       Low 42°F

Top Attractions Around Siena, IT

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


Piazza del Campo
Siena Cathedral
Santa Maria alle Scotte Polyclinic
University of Siena
Banca Monte dei Paschi di Siena
Fortezza Medicea
Porta Camollia
Fonte Gaia
San Martino
Siena State Archives
Palazzo Pubblico
Porta Romana
Museo dell'Opera del Duomo
Basilica di Santa Maria dei Servi
Fontebranda
Siena Baptistry
Civic Museum
Piazza Salimbeni
Casa di Santa Caterina
Siena Stadium

Other Places to Stay in Siena, IT


Agostoli 1,752 Properties
Le Tolfe 1,709 Properties
Castagno 1,627 Properties
Costalpino 1,615 Properties
Siena Historical Center 1,321 Properties
Siena City Centre 1,321 Properties
Sant'Andrea 1,226 Properties
Montecchio 1,118 Properties
Taverne d'Arbia 375 Properties
Montechiaro 252 Properties
lsola d'Arbia 239 Properties
Vico D'arbia 209 Properties

Frequently Asked Questions About Siena?

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

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

Discover 36 accommodations with private or nearby pickleball courts in Siena. Some of the best destinations to stay and play pickleball are:

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

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

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 1460 properties listed in Siena 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 (3) 
Neighborhood Property Count
Siena Historical Center Vacation Rentals in Siena, Tuscany 1321
Siena City Centre Vacation Rentals in Siena, Tuscany 1321
Montarioso Vacation Rentals in Siena, Tuscany 1667

People Also Ask

There are 1460 Siena, IT Vacation Rentals

Recently Booked Vacation Rentals in Siena