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2775+ Simcoe County Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Simcoe County

Discover more than 2775 holiday rentals in Simcoe County. Rent By Owner holiday homes has everything you need to find a place to stay near Simcoe County, ON.

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

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Frequently Asked Questions About Simcoe County Holiday Rentals

There are a lot of options in Simcoe County. If you plan on staying in the Simcoe County 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 Simcoe County:

There are many holiday rentals available in Simcoe County; however, here are a few of the most popular holiday homes listed in Simcoe County 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 Simcoe County to find one that works for you.
Yes, there are 2775 self-catering family homes and holiday rentals in Simcoe County.
There are more than 2775 luxury holiday homes in or near Simcoe County, according to 2025 data from Rent By Owner. Consider these homes for your next holiday: