Vacation Home Rentals By Owner In Sheboygan, WI

Showing 20 Of 64 Vacation Rentals

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

Exceptional(10)

$640.71

/ Nightly

Private Vacation Home

Peaceful 4 BDRM Lake Michigan Retreat - Perfect for Friends and Families

Sheboygan, Wisconsin, United States

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Bath

Sleeps

Exceptional(11)

$1003.84

/ Nightly

Private Vacation Home

Lakeview Farm | Beach · Hot Tub · Theater · Views

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$999.86

/ Nightly

Private Vacation Home

Whistling Straights 4 min, Blackwolf Run 7 min, Erin Hills 84 min, 3 Bedroom

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(1)

$711.65

/ Nightly

Private Vacation Home

Luxury Pool Retreat - 2 Acres - Near Whistling Straits

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(25)

$945.85

/ Nightly

Private Vacation Home

Boutique Gallery House - Stay inside a Work of Art

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(4)

$939.78

/ Nightly

Private Vacation Home

Pelican Point - Private Retreat - just 4 miles to downtown Sheboygan

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(43)

$914.81

/ Nightly

Private Vacation Home

Luxury Home Historic location 4BR-3 FullBath- Walk 3 min beach, 10 to downtown

Sheboygan, Wisconsin, United States

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Bath

Sleeps

Exceptional(12)

$879.63

/ Nightly

Private Vacation Home

Modern Lake Michigan House with Treehouse

Sheboygan, Wisconsin, United States

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Bath

Sleeps

$868.85

/ Nightly

Private Vacation Home

Captain`s Quarters | Lake Michigan views for 14

Sheboygan, Wisconsin, United States

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Bath

Sleeps

Exceptional(17)

$961.35

/ Nightly

Private Vacation Home

Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(8)

$725.3

/ Nightly

Private Vacation Home

Walk to Beach & Pier | Fully-Loaded Kitchen

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(21)

$706.54

/ Nightly

Private Vacation Home

Pet-Friendly Sheboygan Home, 1 Mi to Lake Michigan

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(132)

$655.47

/ Nightly

Private Vacation Home

Lake Michigan Home with gorgeous views, great spot for family or golf retreat

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(42)

$599.29

/ Nightly

Private Vacation Home

Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(1)

$537.03

/ Nightly

Private Vacation Home

Beachside Beautifully Renovated Historic Home

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(13)

$528.35

/ Nightly

Private Vacation Home

Sheboygan Shores

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(21)

$490.7

/ Nightly

Private Vacation Home

NEW! Charming 3BR/2BA Lake House in the Woods of the desirable Black River area

Sheboygan, Wisconsin, United States

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Bath

Sleeps

Exceptional(81)

$476.71

/ Nightly

Private Vacation Home

Beach and Golf House

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

Rent a place that suits your needs

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Private vacation home

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Most popular vacation rentals in Sheboygan

Exceptional(4)

$327.49

/ Nightly

Cottage

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

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(4)

$277.99

/ Nightly

Condo

Beachside Condo Downtown with Lake Michigan Views

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(4)

$289.43

/ Nightly

Private vacation home

REMODELED HOME ON LAKE MICHIGAN

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(4)

$301.91

/ Nightly

Private vacation home

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

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(4)

$302.48

/ Nightly

Condo

The Cottage | Beachfront Condo on Lake Michigan

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(4)

$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

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Bath

Sleeps

Exceptional(4)

$312.98

/ Nightly

Condo

Malibu of the Midwest Condo steps from the Lake

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(4)

$321.43

/ Nightly

Private vacation home

Steps from Lake Michigan: North Point Place

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(4)

$354.69

/ Nightly

Private vacation home

Cozy Corner Cottage| Beach Access & Historic Charm

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(4)

$349.02

/ Nightly

Villa

Wandering Waves | Beachfront Lake Michigan Stay!

Sheboygan, Wisconsin, United States

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Bath

Sleeps

Vacation Home Rentals By Owner In Sheboygan, WI

$729.24

$640.71

$1003.84

$999.86

$711.65

$945.85

$939.78

$914.81

$879.63

$868.85

$961.35

$725.3

$706.54

$655.47

$599.29

$537.03

$528.35

$490.7

$476.71

$467.91

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