126+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  3. Cupertino

Cupertino pickleball Stays, Resort Rentals, & Homes

About Cupertino Vacation Rentals

Discover over 126 amazing vacation rental options in Cupertino 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 Cupertino.

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 547.82 ft², with prices averaging US $249 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 Cupertino.

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Top Pickleball-Ready Accommodation Types in Cupertino

Type Count
Holiday Apartments 52
Vacation Homes 36
Cottages 2

Use these Quick Filters to Find a Vacation Rental in Cupertino

★ 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 Cupertino with PickleTrip™.

Weather in Cupertino, CA

View the weather forecast for Cupertino before booking your Cupertino Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Cupertino, CA

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


Apple Campus
Apple Park Visitor Center
DeAnza College
Blackberry Farm Golf Course
McClellan Ranch Park
Cupertino Memorial Park
Vallco Shopping Mall
Massage Envy Spa
West Coast Farmers Market
Bowlmor Lanes
Flint Center for the Performing Arts
Cupertino Historical Society and Museum
Euphrat Museum of Art
Levi's Stadium
Stanford University
SAP Center at San Jose
San Jose Convention Center
San Francisco Bay
Winchester Mystery House
Santa Clara Convention Center

Other Places to Stay in Cupertino, CA


Rancho Rinconada 555 Properties
Apple Park Visitor Center 531 Properties
Vallco Shopping Mall 444 Properties
Apple Campus 437 Properties
Bowlmor Lanes 335 Properties
Massage Envy Spa 314 Properties
Cupertino Historical Society and Museum 306 Properties
Euphrat Museum of Art 270 Properties
Cupertino Memorial Park 267 Properties
DeAnza College 256 Properties
West Coast Farmers Market 254 Properties
Flint Center for the Performing Arts 250 Properties

Frequently Asked Questions About Cupertino?

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

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

Discover 20 accommodations with private or nearby pickleball courts in Cupertino. Some of the best destinations to stay and play pickleball are:

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

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

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 126 properties listed in Cupertino in 2026, 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 (5) 
Neighborhood Property Count
Sunnyvale West Vacation Rentals in Cupertino, California 208
West San Jose Vacation Rentals in Cupertino, California 66
Rancho Rinconada Vacation Rentals in Cupertino, California 555
Woodland Acres - The Highlands Vacation Rentals in Cupertino, California 246
South Los Altos Vacation Rentals in Cupertino, California 443

People Also Ask

There are 126 Cupertino, CA Vacation Rentals

Recently Booked Vacation Rentals in Cupertino