774+ Private Villas and Holiday Rentals in Sheboygan |
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Sheboygan Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Sheboygan

Discover more than 774 vacation rentals available in Sheboygan. 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 Sheboygan.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Sheboygan, 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 Sheboygan. On average, places to stay near Sheboygan offer 867.01 ft², with nightly prices averaging ZA R7,349.

With Casai, finding and comparing holiday rentals in Sheboygan 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 Sheboygan

Type Count
Vacation Homes 402
Holiday Apartments 140
Villas 31
Cottages 21

Use these Quick Filters to Find a Holiday Rental in Sheboygan

★ 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 Sheboygan.

Weather in Sheboygan, WI

View the weather forecast for Sheboygan before booking your Sheboygan Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Sheboygan, WI

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


Whistling Straits Golf Course
Blue Harbor Resort & Conference Center Water Park
Road America
Kettle Moraine State Forest
Wisconsin Maritime Museum
Kohler Design Center
Lincoln Park Zoo
Blackwolf Run
Skip Barber Driving School
Kohler-Andrae State Park
John Michael Kohler Arts Center
University of Wisconsin-Sheboygan
Chilton Speedway
St. Peter Claver Parish
Children's Museum
Wade House Historic Site
The Bull at Pinehurst Farms Golf Course
Hamilton Wood Type and Printing Museum
Stefanie H. Weill Center for the Performing Arts
Harrington Beach State Park

Other Places to Stay in Sheboygan, WI


Sheboygan County 589 Properties
Downtown 242 Properties
Ellis Historical District 201 Properties
Rhine 126 Properties
Elkhart Lake 126 Properties
Plymouth 114 Properties
Sheboygan Falls 97 Properties
Two Rivers 74 Properties
Manitowoc 71 Properties
Calumet County 47 Properties
Campbellsport 41 Properties
Chilton 38 Properties

Frequently Asked Questions About Sheboygan?

What are the top holiday rentals in Sheboygan?

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

How many holiday rentals have private pools in Sheboygan?

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

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

How many Casai.co.za holiday rentals are available in Sheboygan?

As of 2025, Casai boasts over 774 properties listed in the Sheboygan area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Sheboygan.

Nearby Neighborhood (3) 
Neighborhood Property Count
Downtown Vacation Rentals in Sheboygan, Wisconsin 242
Ellis Historical District Vacation Rentals in Sheboygan, Wisconsin 201
Raider Vacation Rentals in Sheboygan, Wisconsin 200

People Also Ask

There are 774 Sheboygan, WI Holiday Rentals

Recently Booked Holiday Rentals in Sheboygan