Vacation Home Rentals By Owner In Sheboygan, WI

Showing 60 Of 64 Vacation Rentals

$2164.67

/ Nightly

Private Vacation Home

Private, 4-bedroom, 2.5-bath near Kohler golf & walking distance to winery!

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(12)

$879.63

/ Nightly

Private Vacation Home

Modern Lake Michigan House with Treehouse

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(49)

$370.58

/ Nightly

Private Vacation Home

Coastal Comfort & Golfers' Paradise in Sheboygan!

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(19)

Select Dates for Price

Private Vacation Home

Good Vibes on the Third Coast-Pet Friendly! Cozy and Close by!

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$246.3

/ Nightly

Private Vacation Home

Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(174)

$289.43

/ Nightly

Private Vacation Home

REMODELED HOME ON LAKE MICHIGAN

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(193)

$308.72

/ Nightly

Private Vacation Home

2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(17)

$340.51

/ Nightly

Private Vacation Home

BEACHVIEW GETAWAY

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(1)

$341.64

/ Nightly

Private Vacation Home

Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair

Sheboygan, Wisconsin, United States

Bed

Bath

Exceptional(12)

$354.69

/ Nightly

Private Vacation Home

Cozy Corner Cottage| Beach Access & Historic Charm

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(2)

$355.77

/ Nightly

Private Vacation Home

Black River Retreat Eclectic-Unique-Intriguing

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(30)

$359.91

/ Nightly

Private Vacation Home

LUXE Manor with Modern, Elegant Vibes

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(30)

$366.27

/ Nightly

Private Vacation Home

New King Park Beach Lookout Deluxe! 3BR Right at Lake!

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(2)

$729.24

/ Nightly

Private Vacation Home

4- Bedroom Retreat with Sauna, Game Room, Patio & Walk to Bars & Restaurants

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$382.88

/ Nightly

Private Vacation Home

Sunset Vista- cozy two bedroom retreat

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(42)

$412.58

/ Nightly

Private Vacation Home

The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$416.35

/ Nightly

Private Vacation Home

Windward House - Entire home in Sheboygan

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$421.09

/ Nightly

Private Vacation Home

Lakeside Daydream - Walk to Lake Michigan!

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(4)

$467.91

/ Nightly

Private Vacation Home

Sheboygan Chalet | Nature, Arcade, Sauna & Hot Tub

Sheboygan, Wisconsin, United States

Bath

Sleeps

Exceptional(81)

$476.71

/ Nightly

Private Vacation Home

Beach and Golf House

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Rent a place that suits your needs

Condo

View 26 Condo

Private vacation home

View 64 Private vacation home

Most popular vacation rentals in Sheboygan

Exceptional(81)

$327.49

/ Nightly

Cottage

Lake Breeze Cottage. One block from the lake, walking distance to downtown!

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(81)

$277.99

/ Nightly

Condo

Beachside Condo Downtown with Lake Michigan Views

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(81)

$289.43

/ Nightly

Private vacation home

REMODELED HOME ON LAKE MICHIGAN

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(81)

$301.91

/ Nightly

Private vacation home

4BR Home Near Kohler. Fall Getaway. Sleeps 7.

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(81)

$302.48

/ Nightly

Condo

The Cottage | Beachfront Condo on Lake Michigan

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(81)

$308.72

/ Nightly

Private vacation home

2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(81)

$312.98

/ Nightly

Condo

Malibu of the Midwest Condo steps from the Lake

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(81)

$321.43

/ Nightly

Private vacation home

Steps from Lake Michigan: North Point Place

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(81)

$354.69

/ Nightly

Private vacation home

Cozy Corner Cottage| Beach Access & Historic Charm

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(81)

$349.02

/ Nightly

Villa

Wandering Waves | Beachfront Lake Michigan Stay!

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Vacation Home Rentals By Owner In Sheboygan, WI

$2164.67

$879.63

$370.58

$246.3

$289.43

$308.72

$340.51

$341.64

$354.69

$355.77

$359.91

$366.27

$729.24

$382.88

$412.58

$416.35

$421.09

$467.91

$476.71

Rent a place that suits your needs

Most popular vacation rentals in Sheboygan

$327.49

$277.99

$289.43

$301.91

$302.48

$308.72

$312.98

$321.43

$354.69

$349.02

Most Popular Cities in Wisconsin