39+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. Canada
  2. Ontario
  3. Toronto
  4. Upper Beaches

Upper Beaches pickleball Stays, Resort Rentals, & Homes

About Upper Beaches Vacation Rentals

Discover over 39 amazing vacation rental options in Upper Beaches 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 Upper Beaches.

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 420.93 ft², with prices averaging US $136 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 Upper Beaches.

Show more
Show less

Top Pickleball-Ready Accommodation Types in Upper Beaches

Type Count
Holiday Apartments 20
Vacation Homes 19

Use these Quick Filters to Find a Vacation Rental in Upper Beaches

★ 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 Upper Beaches with PickleTrip™.

Weather in Upper Beaches, ON

View the weather forecast for Upper Beaches before booking your Upper Beaches 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 Upper Beaches, ON


Beach Hill 26 Properties

Frequently Asked Questions About Upper Beaches?

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

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

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

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 39 properties listed in Upper Beaches 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 (12) 
Neighborhood Property Count
Scarborough Vacation Rentals in Toronto, Ontario 254
Old East York Vacation Rentals in Toronto, Ontario 53
Leslieville Vacation Rentals in Toronto, Ontario 39
Beach Hill Vacation Rentals in Toronto, Ontario 26
The Beaches Vacation Rentals in Toronto, Ontario 26
Woodbine - Lumsden Vacation Rentals in Toronto, Ontario 484
Birch Cliff Vacation Rentals in Toronto, Ontario 112
Fallingbrook Vacation Rentals in Toronto, Ontario 106
The Danforth Vacation Rentals in Toronto, Ontario 919
East Danforth Vacation Rentals in Toronto, Ontario 535
Greenwood - Coxwell Vacation Rentals in Toronto, Ontario 893
The Beach Triangle Vacation Rentals in Toronto, Ontario 509

People Also Ask

There are 39 Upper Beaches, ON Vacation Rentals

Recently Booked Vacation Rentals in Upper Beaches