309+ Private Villas and Holiday Rentals in Windermere |
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Windermere Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Windermere

Discover more than 309 vacation rentals available in Windermere. 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 Windermere.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Windermere, 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 Windermere. On average, places to stay near Windermere offer 1163.97 ft², with nightly prices averaging $1,267.

With Casai, finding and comparing holiday rentals in Windermere 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 Windermere

Type Count
Cottages 205
Vacation Homes 59
Villas 11
Holiday Apartments 3

Use these Quick Filters to Find a Holiday Rental in Windermere

★ 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 Windermere.

Weather in Windermere, ON

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

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


Windermere Golf & Country Club
Windermere Marina
Arrowhead Provincial Park
Lake Muskoka
Lake of Bays
Lake Rosseau
Torrance Barrens Dark-Sky Preserve
Santa's Village
Lake Joseph
Taboo Golf Course
Muskoka Lakes Winery
Lake Joseph Golf Club
Muskoka Wharf
Skeleton Lake
Rocky Crest Golf Club
Huntsville Civic Center Algonquin Theater
Gravenhurst Opera House
Muskoka Brewery
Diamond In The Ruff Golf Course
Lake of Bays Brewing Company

Other Places to Stay in Windermere, ON


Windermere Marina 72 Properties
Windermere Golf & Country Club 71 Properties

Frequently Asked Questions About Windermere?

What are the top holiday rentals in Windermere?

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

How many holiday rentals have private pools in Windermere?

Discover a selection of holiday rentals with private pools near Windermere with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Windermere are best for families?

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

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

As of 2025, Casai boasts over 309 properties listed in the Windermere area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Windermere.


People Also Ask

There are 309 Windermere, ON Holiday Rentals

Recently Booked Holiday Rentals in Windermere