39+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. Canada
  2. Prince Edward Island
  3. O'Leary

O'Leary pickleball Stays, Resort Rentals, & Homes

About O'Leary Vacation Rentals

Discover over 39 amazing vacation rental options in O'Leary 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 O'Leary.

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 554.46 ft², with prices averaging US $279 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 O'Leary.

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Top Pickleball-Ready Accommodation Types in O'Leary

Type Count
Cottages 18
Vacation Homes 12
Villas 1

Use these Quick Filters to Find a Vacation Rental in O'Leary

★ 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 O'Leary with PickleTrip™.

Weather in O'Leary, PE

View the weather forecast for O'Leary before booking your O'Leary 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 O'Leary, PE

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


Mill River Golf Course
Prince Edward Island Potato Museum
Mill River Provincial Park
Kouchibouguac National Park
West Point Lighthouse
St. Simon and St. Jude Church
Green Park Shipbuilding Museum & Yeo House
Irving Arboretum
Alberton Museum
St Felix Golf Course
Pointe a Jerome Range Lighthouse
Fisherman's Haven Park
Dixon Point Range Lighthouse
Irish Moss Interpretive Centre
Cedar Dunes Provincial Park
Northport Range Rear Lighthouse
Ellerslie Shellfish Museum
Big Tignish Lighthouse
Irving Eco-Centre
Olivier Soapery

Other Places to Stay in O'Leary, PE


Prince Edward Island Potato Museum 32 Properties
Cape Wolfe 31 Properties
Mill River Provincial Park 31 Properties
Mill River Golf Course 31 Properties

Frequently Asked Questions About O'Leary?

What are the top vacation rentals, resorts, and hotels in O'Leary 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 O'Leary. 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 O'Leary!

How many PickleTrip vacation rentals or resorts are available in O'Leary?

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 O'Leary 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.


People Also Ask

There are 39 O'Leary, PE Vacation Rentals

Recently Booked Vacation Rentals in O'Leary