Airbnb Management
Full-service Airbnb management for your short-term rental. Nationwide.
Sheboygan, Wisconsin
In Sheboygan, Wisconsin, guests can find a variety of Airbnb accommodations that cater to different preferences and needs. Options range from cozy, rustic cabins and charming cottages that offer a peaceful retreat near the scenic shores of Lake Michigan, to modern apartments and homes located in the heart of the city, providing easy access to local attractions and dining. For those seeking a unique experience, there are also historic homes and converted barns that offer a blend of character and comfort. Whether visitors are looking for a quiet getaway or a convenient base for exploring the area, Sheboygan's diverse Airbnb offerings provide a welcoming and comfortable stay.
As of the latest information, Sheboygan, Wisconsin, does not have specific laws governing short-term rentals like Airbnb. However, property owners must comply with general zoning regulations and any applicable state laws. Hosts are typically required to collect and remit state sales tax and local room tax on short-term rentals. The state of Wisconsin mandates a 5% sales tax, and Sheboygan imposes an additional room tax, which is currently set at 8%. Property owners should ensure they are registered with the Wisconsin Department of Revenue to handle these tax obligations properly. It's advisable for hosts to stay informed about any potential changes in local ordinances that may affect short-term rental operations.
Managing an Airbnb in Sheboygan, Wisconsin, involves several key tasks to ensure a smooth operation and positive guest experiences. Hosts need to focus on maintaining the property, which includes regular cleaning, restocking essentials, and addressing any maintenance issues promptly. Effective communication with guests is crucial, from providing clear check-in instructions to being responsive to inquiries and concerns. Additionally, optimizing the listing with accurate descriptions and appealing photos can help attract more bookings. Hosts should also stay informed about local regulations and compliance requirements for short-term rentals in Sheboygan. Finally, implementing a dynamic pricing strategy can help maximize occupancy and revenue, taking into account seasonal demand and local events.
Sheboygan, Wisconsin, offers several appealing areas for Airbnb stays, each with its unique charm. Downtown Sheboygan is a vibrant choice, featuring a mix of historic architecture, local shops, and a variety of dining options, all within walking distance to the beautiful Lake Michigan shoreline and the John Michael Kohler Arts Center. For those seeking a more tranquil experience, the South Pier District provides picturesque views of the marina and easy access to the South Pier Parlor and Blue Harbor Resort. Meanwhile, the nearby town of Kohler offers a luxurious escape with its world-renowned golf courses and the Kohler Design Center. Each area provides a distinct taste of Sheboygan's welcoming atmosphere and natural beauty.
Sheboygan, Wisconsin, presents a promising market for Airbnb investment due to its scenic location along the shores of Lake Michigan and its reputation as the "Malibu of the Midwest." The city attracts visitors year-round with its beautiful beaches, vibrant arts scene, and outdoor recreational activities, including sailing, fishing, and golfing. Additionally, Sheboygan hosts various events and festivals, such as the annual Sheboygan Bratwurst Days and the Kohler Food & Wine Experience, which draw tourists from across the region. The relatively low property prices compared to larger urban areas make it an attractive option for investors seeking to capitalize on the growing demand for short-term rentals. With its blend of natural beauty and cultural attractions, Sheboygan offers a unique opportunity for Airbnb investors looking to tap into a market with both seasonal and year-round appeal.
As of the latest data, the average Airbnb revenue for properties in Sheboygan, Wisconsin, reflects a modest but steady income stream for hosts. The city's appeal, largely driven by its proximity to Lake Michigan and local attractions such as the John Michael Kohler Arts Center and the Sheboygan County Historical Museum, contributes to a consistent demand for short-term rentals. Hosts in Sheboygan typically see a variation in revenue depending on the season, with summer months generally bringing higher occupancy rates and increased earnings due to the influx of tourists seeking outdoor activities and events. Overall, while not as high as in major metropolitan areas, the average Airbnb revenue in Sheboygan provides a reliable supplementary income for property owners, particularly those who capitalize on peak tourist seasons and maintain well-reviewed accommodations.
Sheboygan, Wisconsin, experiences a moderate occupancy rate for Airbnbs, with notable fluctuations due to its seasonal appeal. The summer months, particularly June through August, see a significant increase in occupancy as tourists flock to the area to enjoy Lake Michigan's beaches, water activities, and local festivals. This peak season often results in higher booking rates and limited availability. Conversely, the winter months tend to have lower occupancy rates, as the colder weather and reduced outdoor activities lead to a decline in tourist visits. However, some winter sports enthusiasts and those seeking a quiet retreat may still contribute to bookings during this period. Overall, Sheboygan's Airbnb market is characterized by its seasonal variations, with summer being the most popular time for visitors.
Why Choose Checkmate Rentals?
![]() | Other Property Managers | |
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Cost | Starting at 15% fee | 25-40% fee |
Guest Communications | Guest response within 10 minutes, 24 hours a day | Sporadic guest communications |
Host Communications | Designated host call in phone line | Bot response assistants |
Insurance | Full damage protection for every reservation | Unreliable insurance coverage |
Contract | No annual agreements | Contract lock-ins |
Checkmate Rentals

Attract Guests
List on top booking sites
Optimize listings for SEO
Feature show-stopping photos
Competitive, dynamic pricing
Mangage Operations
Tailored pricing algorithms
24/7 guest service
Reliable, professional cleaning
Restocking & inventory management
Maintenance coordination


Host Care
Unlimited owner stays
Flexible contract options
East to use host portal
Set it and forget it billing
Exclusive insurance discounts via our partner network
Get in touch with us.

Checkmate Rentals is a full-service property manager. That means the Airbnb listing, the home, the guest and the work is our responsibility.
Local Team Support
Know that you have a friendly, accessible team right up the road to handle any property needs.
Guest Screenings
Book only the most qualified guests 25 and over who’ll enjoy your home the right way.
Unlimited Owner Use
Block off your vacation days with ease, and enjoy your home as often as you want.
Reliable Property Maintenance
Keep your home running smoothly around the clock with a fast, reliable maintenance team.
Transparent Finances
Transparent Finances Booking payouts get paid directly to you for full financial transparency. We never handle your money.
Fast 24/7 Guest Communication
Make every guest feel cared for with industry best response times of 1-15 minutes day and night.
Marketing
Target, attract & book qualified guests with photography, email marketing, and optimized listings.
Revenue Management
Get the competitive edge with dynamic pricing and rates optimized daily by your pricing manager.

Ready to make the jump?
Let's get started! Schedule a call today to learn more about Checkmate Rentals.