Sheboygan Vacation Rentals

Compare 12 vacation rentals.
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Make Sheboygan your next getaway

Sheboygan

Top Sheboygan property types

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House rentals

View 7 House rentals
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Apartments

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Studios

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Popular amenities for Sheboygan vacation rentals

Popular
Dog-friendly Internet Lake view
2 Mi to Dtwn: Studio Suite in Sheboygan
0 Bedroom | 1 Bath | Sleeps 2

2 Mi to Dtwn: Studio Suite in Sheboygan - Sheboygan, WI

$139 avg / night
(excludes fees and taxes)
Large Backyard, Walk to Hospital: Sheboygan Abode!
2 Bedroom | 1 Bath | Sleeps 7

Large Backyard, Walk to Hospital: Sheboygan Abode! - Sheboygan, WI

$153 avg / night
(excludes fees and taxes)
Dog-Friendly Sheboygan Home - 1 Mi to Town!
1 Bedroom | 1 Bath | Sleeps 2

Dog-Friendly Sheboygan Home - 1 Mi to Town! - Sheboygan, WI

$127 avg / night
(excludes fees and taxes)
5.0 (6)
Pet-Friendly Sheboygan Home, 1 Mi to Lake Michigan
4 Bedroom | 1.5 Bath | Sleeps 10

Pet-Friendly Sheboygan Home, 1 Mi to Lake Michigan - Sheboygan, WI

$150 avg / night
(excludes fees and taxes)
5.0 (3)
Sheboygan Getaway w/ Deck + On-Site Lake Access!
2 Bedroom | 1 Bath | Sleeps 5

Sheboygan Getaway w/ Deck + On-Site Lake Access! - Sheboygan, WI

$265 avg / night
(excludes fees and taxes)
5.0 (3)

View 7 more homes

Browse more vacation rental amenities in Sheboygan

Ocean view | Water view | Waterfront | A/C | Elevator | Washer/dryer | Balcony | Bikes | Ping-pong table | Beach access

Recent Sheboygan guest reviews

Couldn’t have asked for a better host. Super clean home. I would definitely come back!
Dave . | Oct 2025
Despite the fact that I’m not a city girl, I was really happy to see the house was absolutely adorable… Very clean, comfortable and easily accessible to various areas in Sheboygan… Came to town to visit friends and I was in the right neighborhood… And of course, being pet friendly so appreciate that would highly recommend!!
Linda . | Oct 2025
The place was nice and my family enjoyed our stay.
Vang . | Sep 2025
Sheboygan vacation rental FAQ

Yes, 6 of our Sheboygan homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 17 of our Sheboygan vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Sheboygan vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find the check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Sheboygan team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Sheboygan, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons cleaning
Professional cleaning

Nearby destinations

Great Lakes   |   Lake Michigan   |   Southern Wisconsin   |   Plymouth   |   Elkhart Lake   |   Kiel   |   Campbellsport   |   Wisconsin
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