589+ Private Villas and Holiday Rentals in Windsor |
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Windsor Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Windsor

Discover more than 589 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 1105.7 ft², with nightly prices averaging US $206.

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.

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Top Accommodation Types in Windsor

Type Count
Vacation Homes 255
Holiday Apartments 151
Cottages 87
Villas 4

Use these Quick Filters to Find a Holiday Rental in Windsor

★ 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 Windsor.

Weather in Windsor, ON

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

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


Caesars Casino
Detroit Windsor Tunnel
Point Pelee National Park
Caesar's Windsor
University of Windsor
Adventure Bay Family Water Park
The Colosseum
Jackson Park
St. Clair College
Devonshire Mall
Windsor Family Credit Union Centre
Leamington Arts Centre
Ambassador Golf Club
Coventry Gardens
Dieppe Gardens
Leamington Municipal Marina
Willistead Manor
Ontario Travel Information Centre - Windsor
Olde Walkerville Neighborhood
Walkerville Brewery

Other Places to Stay in Windsor, ON


McGregor 395 Properties
South Central 224 Properties
Bridgeview 202 Properties
East Windsor 179 Properties
Leamington 143 Properties
Sandwich Towne 116 Properties
Tecumseh 114 Properties
Riverside 78 Properties
Walkerville 45 Properties
Wheatley 28 Properties
Amherstburg 24 Properties
LaSalle 24 Properties

Frequently Asked Questions About Windsor?

What are the top holiday rentals in Windsor?

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

How many holiday rentals have private pools in Windsor?

Discover a selection of holiday rentals with private pools near Windsor 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 Windsor are best for families?

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

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

As of 2025, Casai boasts over 589 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 45
Bridgeview Vacation Rentals in Windsor, Ontario 202
East Windsor Vacation Rentals in Windsor, Ontario 179
Riverside Vacation Rentals in Windsor, Ontario 78
Romney Vacation Rentals in Windsor, Ontario 59
South Central Vacation Rentals in Windsor, Ontario 224
Sandwich Towne Vacation Rentals in Windsor, Ontario 116

People Also Ask

There are 589 Windsor, ON Holiday Rentals

Recently Booked Holiday Rentals in Windsor