Windsor Holiday Rentals

Compare Villas, Resorts, & Rentals in Windsor, Ontario, Canada

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10.0 (2 Reviews)
7 Bedrooms 16 Guests
From CA $351 per night
New
1 Bedroom 2 Guests
10.0 (59 Reviews)
1 Bedroom 2 Guests
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10.0 (2 Reviews)
5 Bedrooms 17 Guests
From CA $211 per night
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10.0 (110 Reviews)
1 Bedroom 2 Guests
10.0 (55 Reviews)
2 Bedrooms 6 Guests
From CA $64 per night
10.0 (2 Reviews)
3 Bedrooms 6 Guests
From CA $199 per night
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10.0 (72 Reviews)
1 Bedroom 2 Guests
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10.0 (1 Review)
1 Bedroom 2 Guests
10.0 (43 Reviews)
2 Bedrooms 6 Guests
10.0 (1 Review)
2 Bedrooms 6 Guests
10.0 (37 Reviews)
2 Bedrooms 4 Guests
From CA $66 per night
10.0 (1 Review)
1 Bedroom 2 Guests
From CA $576 per night
10.0 (37 Reviews)
2 Bedrooms 8 Guests
10.0 (1 Review)
1 Bedroom 2 Guests
From CA $138 per night
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9.8 (57 Reviews)
2 Bedrooms 4 Guests
10.0 (23 Reviews)
2 Bedrooms 4 Guests
From CA $155 per night
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9.8 (56 Reviews)
2 Bedrooms 3 Guests
10.0 (20 Reviews)
2 Bedrooms 6 Guests
From CA $419 per night
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9.8 (10 Reviews)
3 Bedrooms 6 Guests
From CA $259 per night
10.0 (18 Reviews)
1 Bedroom 4 Guests
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9.7 (3 Reviews)
2 Bedrooms 4 Guests
10.0 (14 Reviews)
2 Bedrooms 4 Guests
From CA $80 per night
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9.6 (25 Reviews)
1 Bedroom 2 Guests
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9.5 (148 Reviews)
2 Bedrooms 6 Guests
10.0 (12 Reviews)
1 Bedroom 2 Guests
From CA $163 per night
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9.5 (41 Reviews)
2 Bedrooms 4 Guests
10.0 (10 Reviews)
2 Bedrooms 4 Guests
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9.5 (13 Reviews)
2 Bedrooms 6 Guests
10.0 (8 Reviews)
1 Bedroom 3 Guests
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9.5 (4 Reviews)
1 Bedroom 2 Guests
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9.5 (2 Reviews)
3 Bedrooms 6 Guests
10.0 (5 Reviews)
2 Bedrooms 6 Guests
9.5 (2 Reviews)
1 Bedroom 4 Guests
10.0 (5 Reviews)
2 Bedrooms 6 Guests
10.0 (4 Reviews)
2 Bedrooms 4 Guests
From CA $351 per night
10.0 (2 Reviews)
2 Bedrooms 6 Guests
10.0 (2 Reviews)
2 Bedrooms 4 Guests
10.0 (2 Reviews)
2 Bedrooms 4 Guests
9.8 (6 Reviews)
2 Bedrooms 4 Guests
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9.4 (8 Reviews)
2 Bedrooms 5 Guests
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10.0 (3 Reviews)
1 Bedroom 2 Guests
From CA $402 per night
9.8 (6 Reviews)
2 Bedrooms 4 Guests
From CA $118 per night
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9.1 (172 Reviews)
4 Bedrooms 8 Guests
From CA $142 per night
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9.6 (356 Reviews)
1 Bedroom 2 Guests
9.8 (6 Reviews)
2 Bedrooms 7 Guests
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9.0 (25 Reviews)
3 Bedrooms 6 Guests
From CA $160 per night
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9.6 (106 Reviews)
1 Bedroom 2 Guests
9.8 (6 Reviews)
1 Bedroom 3 Guests
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9.0 (14 Reviews)
2 Bedrooms 4 Guests
9.6 (41 Reviews)
2 Bedrooms 6 Guests
9.0 (6 Reviews)
2 Bedrooms 5 Guests
9.6 (26 Reviews)
2 Bedrooms 4 Guests
From CA $79 per night
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9.0 (3 Reviews)
1 Bedroom 4 Guests
9.6 (18 Reviews)
1 Bedroom 3 Guests
9.0 (2 Reviews)
1 Bedroom 2 Guests
From CA $173 per night
9.6 (10 Reviews)
1 Bedroom 3 Guests
From CA $183 per night
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9.0 (1 Review)
1 Bedroom 2 Guests
9.6 (7 Reviews)
1 Bedroom 3 Guests
9.0 (1 Review)
3 Bedrooms 6 Guests
9.6 (5 Reviews)
1 Bedroom 3 Guests
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8.9 (45 Reviews)
3 Bedrooms 6 Guests
9.6 (5 Reviews)
2 Bedrooms 4 Guests
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8.8 (23 Reviews)
8 Bedrooms 23 Guests
9.4 (51 Reviews)
2 Bedrooms 4 Guests
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8.8 (15 Reviews)
1 Bedroom 3 Guests

About Casai's Private Villas and Holiday Rentals in Windsor

Discover more than 628 vacation rentals available in Windsor. 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 Windsor.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Windsor, 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 Windsor. On average, places to stay near Windsor offer 1026.12 ft², with nightly prices averaging CA $270.

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

Frequently Asked Questions About Windsor?

What are the top holiday rentals in Windsor?

How many Casai.ca holiday rentals are available in Windsor?

As of 2025, Casai boasts over 628 properties listed in the Windsor area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Windsor.

Nearby Neighborhood (7)

Neighborhood Property Count
Walkerville Vacation Rentals in Windsor, Ontario 48
Bridgeview Vacation Rentals in Windsor, Ontario 202
Riverside Vacation Rentals in Windsor, Ontario 78
East Windsor Vacation Rentals in Windsor, Ontario 179
Romney Vacation Rentals in Windsor, Ontario 59
South Central Vacation Rentals in Windsor, Ontario 224
Sandwich Towne Vacation Rentals in Windsor, Ontario 116