184+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Oakville pickleball Stays, Resort Rentals, & Homes

About Oakville Vacation Rentals

Discover over 184 amazing vacation rental options in Oakville 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 Oakville.

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 642.27 ft², with prices averaging US $188 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 Oakville.

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Top Pickleball-Ready Accommodation Types in Oakville

Type Count
Vacation Homes 104
Holiday Apartments 37
Villas 3

Use these Quick Filters to Find a Vacation Rental in Oakville

★ 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 Oakville with PickleTrip™.

Weather in Oakville, ON

View the weather forecast for Oakville before booking your Oakville 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

Top Attractions Around Oakville, ON

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


Sheridan College
Coronation Park
Oakville Entertainment Centrum
Oakville Centre for the Performing Arts
Glen Abbey Golf Course
Ifly Toronto Oakville
Oakville Galleries
Gairloch Gardens
Kerr Village
Oakville Art Society
Joshua Creek Heritage Art Centre
Bronte Heritage Park
Saw-Whet golf course
Oakville Museum
Sovereign House
Cameron's Brewing Company
Canadian Golf Hall Of Fame
Lake Ontario
Bronte Creek Provincial Park

Other Places to Stay in Oakville, ON


Oakville Galleries 270 Properties
Joshua Creek Heritage Art Centre 211 Properties
Oakville Entertainment Centrum 161 Properties
Ifly Toronto Oakville 149 Properties
Clearview 127 Properties
Sheridan College 122 Properties
Canadian Golf Hall Of Fame 121 Properties
Cameron's Brewing Company 112 Properties
Glen Abbey Golf Course 109 Properties
West Oak Trails 89 Properties
Glen Abbey 84 Properties
West Oakville 59 Properties

Frequently Asked Questions About Oakville?

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

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

Discover 4 accommodations with private or nearby pickleball courts in Oakville. Some of the best destinations to stay and play pickleball are:

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

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

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 184 properties listed in Oakville 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 (7) 
Neighborhood Property Count
Sheridan Vacation Rentals in Toronto, Ontario 221
Clarkson-Lorne Park Vacation Rentals in Toronto, Ontario 163
West Oak Trails Vacation Rentals in Toronto, Ontario 89
Glen Abbey Vacation Rentals in Toronto, Ontario 84
West Oakville Vacation Rentals in Toronto, Ontario 59
Clearview Vacation Rentals in Toronto, Ontario 127
Bronte Vacation Rentals in Toronto, Ontario 64

People Also Ask

There are 184 Oakville, ON Vacation Rentals

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