107+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  4. Willowdale

Willowdale pickleball Stays, Resort Rentals, & Homes

About Willowdale Vacation Rentals

Discover over 107 amazing vacation rental options in Willowdale 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 Willowdale.

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 512.48 ft², with prices averaging US $277 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 Willowdale.

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Top Pickleball-Ready Accommodation Types in Willowdale

Type Count
Vacation Homes 34
Holiday Apartments 29
Villas 3

Use these Quick Filters to Find a Vacation Rental in Willowdale

★ 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 Willowdale with PickleTrip™.

Weather in Willowdale, ON

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

December - February
High 23°F       Low 2°F
March - May
High 65°F       Low 12°F
June - August
High 76°F       Low 49°F
September - November
High 65°F       Low 8°F

Other Places to Stay in Willowdale, ON


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St. George's Anglican Church 366 Properties
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Frequently Asked Questions About Willowdale?

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

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

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

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 107 properties listed in Willowdale 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 (7) 
Neighborhood Property Count
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Newtonbrook Vacation Rentals in Toronto, Ontario 59
Bayview Woods - Steeles Vacation Rentals in Toronto, Ontario 335
Bayview Village Vacation Rentals in Toronto, Ontario 327
Bathurst Manor Vacation Rentals in Toronto, Ontario 340
Fisherville Vacation Rentals in Toronto, Ontario 320
St. Andrew - Windfields Vacation Rentals in Toronto, Ontario 329

People Also Ask

There are 107 Willowdale, ON Vacation Rentals

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