Pickering Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Pickering

Discover more than 261 vacation rentals available in Pickering. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Pickering.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Pickering, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Pickering. On average, places to stay near Pickering offer 620.24 ft², with nightly prices averaging US $212.

With Casai, finding and comparing holiday rentals in Pickering is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Pickering

Type Count
Vacation Homes177
Holiday Apartments60
Villas6

Use these Quick Filters to Find a Holiday Rental in Pickering

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Pickering.

Weather in Pickering, ON

View the weather forecast for Pickering before booking your Pickering 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 Pickering, ON

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


Herongate Barn Theatre
Deer Creek North Golf Course
Glen Cedars Golf Club
Luke Andrews Wood Sculptures
AnNonedale Golf and Country Club
CN Tower
Toronto Eaton Centre
Canada's Wonderland
Rogers Centre
Scotiabank Arena
Ripley's Aquarium of Canada
Metro Toronto Convention Centre
Royal Ontario Museum
Toronto Zoo
Casa Loma
Vaughan Mills Mall
University of Toronto - St. George Campus
Royal Alexandra Theatre
Hockey Hall of Fame
Harbourfront Centre

Other Places to Stay in Pickering, ON


Annandale Golf and Country Club 271 Properties
Glen Cedars Golf Club 127 Properties
Deer Creek North Golf Course 63 Properties
Herongate Barn Theatre 44 Properties
Luke Andrews Wood Sculptures 32 Properties

Frequently Asked Questions About Pickering?

What are the top holiday rentals in Pickering?

With numerous options available in Pickering, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Pickering:

Which holiday homes in Pickering are best for families?

If you're searching for a family-friendly holiday home in Pickering, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Pickering:

How many Casai.com holiday rentals are available in Pickering?

As of 2026, Casai boasts over 261 properties listed in the Pickering area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Pickering.

Nearby Neighborhood (1) 

NeighborhoodProperty Count
Scarborough Vacation Rentals in Oshawa, Ontario 258

There are 261 Pickering, ON Holiday Rentals

Recently Booked Holiday Rentals in Pickering