587+ Pickering Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Pickering

Discover more than 587 holiday rentals in Pickering. Rent By Owner holiday homes has everything you need to find a place to stay near Pickering, .

Whether you are looking for luxury villas in Pickering, furnished homes, unique style condos, flats, cozy cottages for a romantic getaway, spacious apartment for family holidays, or stylish accommodation for a business trip, we can help you find the perfect place. Our holiday rentals include top amenities such as indoor/outdoor swimming pools, kitchen facilities, gyms, hot tubs, Internet connectivity, and more.

If you are planning to travel to Pickering with a whole family or group, RBO holiday accommodations make your trip memorable. We have plenty of places to stay in Pickering for families, large parties, or private owner accommodations for long or short trips. Pickering Pet-friendly holiday rentals are available. Book your favorite vacation rentals in Pickering with Rent By Owner. RBO makes it easy to compare and book holiday rentals today.

Show more
Show less

Frequently Asked Questions About Pickering Holiday Rentals

There are a lot of options in Pickering. If you plan on staying in the Pickering area, consider making a reservation for a few nights at one of these properties as these have been rated the top Holiday Home Rentals in Pickering:

There are many holiday rentals available in Pickering; however, here are a few of the most popular holiday homes listed in Pickering on our website:
At Rent By Owner most of our places to stay are perfect for families. Check out the complete list of holiday homes in Pickering to find one that works for you.
Yes, there are 587 self-catering family homes and holiday rentals in Pickering.
There are more than 587 luxury holiday homes in or near Pickering, according to 2025 data from Rent By Owner. Consider these homes for your next holiday: