Home Vacation Rentals By Owner In Sheboygan, WI

Showing 60 Of 122 Vacation Rentals
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Exceptional(12)

$242.9

/ Nightly
Apartment

Overlook Oasis | Coastal Haven in Ellis District

Sheboygan, Wisconsin, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(13)

$341.64

/ Nightly
Apartment

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan

Sheboygan, Wisconsin, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(34)

$130.53

/ Nightly
Apartment

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

Sheboygan, Wisconsin, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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Exceptional(16)

$237.22

/ Nightly
Condo

Sheboygan Sunrise Beach Stay

Sheboygan, Wisconsin, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(8)

$707.49

/ Nightly
Private Vacation Home

Walk to Beach & Pier | Fully-Loaded Kitchen

Sheboygan, Wisconsin, United States

Bed 5

Bed

Bath 4

Bath

Sleep 11

Sleeps
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$2164.67

/ Nightly
Private Vacation Home

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

Sheboygan, Wisconsin, United States

Bed 6

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(132)

$639.69

/ Nightly
Private Vacation Home

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

Sheboygan, Wisconsin, United States

Bed 5

Bed

Bath 3

Bath

Sleep 14

Sleeps
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Exceptional(8)

$220.19

/ Nightly
Apartment

Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI

Sheboygan, Wisconsin, United States

Bed 3

Bed

Bath 1

Bath

Sleep 5

Sleeps
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Exceptional(13)

$211.12

/ Nightly
Apartment

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

Sheboygan, Wisconsin, United States

Bed 3

Bed

Bath 1

Bath

Sleep 5

Sleeps
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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

Bed 3

Bed

Bath 2

Bath

Sleep 9

Sleeps
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Exceptional(2)

$355.77

/ Nightly
Private Vacation Home

Black River Retreat Eclectic-Unique-Intriguing

Sheboygan, Wisconsin, United States

Bed 3

Bed

Bath 2

Bath

Sleep 7

Sleeps
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Exceptional(193)

$306.45

/ 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 2

Bed

Bath 2

Bath

Sleep 5

Sleeps
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Exceptional(12)

$354.69

/ Nightly
Private Vacation Home

Cozy Corner Cottage| Beach Access & Historic Charm

Sheboygan, Wisconsin, United States

Bed 3

Bed

Bath 1

Bath

Sleep 7

Sleeps
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Exceptional(3)

$396.12

/ Nightly
Condo

Riverfront Condo Steps to Downtown & Lake Michigan

Sheboygan, Wisconsin, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(29)

$301.91

/ Nightly
Condo

The Cottage | Beachfront Condo on Lake Michigan

Sheboygan, Wisconsin, United States

Bed 2

Bed

Bath 2

Bath

Sleep 8

Sleeps
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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 4

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(10)

$313.26

/ Nightly
Condo

Fits 7! Beachfront Condo - Handicap Accessible

Sheboygan, Wisconsin, United States

Bed 2

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(17)

$337.1

/ Nightly
Condo

Riverfront Loft - FANTASTIC location w/stunning views - on the boardwalk!

Sheboygan, Wisconsin, United States

Bed 1

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(174)

$289.43

/ Nightly
Private Vacation Home

REMODELED HOME ON LAKE MICHIGAN

Sheboygan, Wisconsin, United States

Bed 3

Bed

Bath 1

Bath

Sleep 7

Sleeps
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Exceptional(12)

$1326.49

/ Nightly
Private Vacation Home

Baronwood Oasis | Pool + Arcade Mega Estate

Sheboygan, Wisconsin, United States

Bed 7

Bed

Bath 5

Bath

Sleep 16

Sleeps
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Home Most popular vacation rentals in Sheboygan

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Exceptional(12)

$327.49

/ Nightly
Cottage

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

Sheboygan, Wisconsin, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(12)

$277.99

/ Nightly
Condo

Beachside Condo Downtown with Lake Michigan Views

Sheboygan, Wisconsin, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(12)

$289.43

/ Nightly
Private vacation home

REMODELED HOME ON LAKE MICHIGAN

Sheboygan, Wisconsin, United States

Bed 3

Bed

Bath 1

Bath

Sleep 7

Sleeps
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Exceptional(12)

$301.91

/ Nightly
Private vacation home

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

Sheboygan, Wisconsin, United States

Bed 4

Bed

Bath 2

Bath

Sleep 7

Sleeps
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Exceptional(12)

$302.48

/ Nightly
Condo

The Cottage | Beachfront Condo on Lake Michigan

Sheboygan, Wisconsin, United States

Bed 2

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(12)

$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 2

Bed

Bath 2

Bath

Sleep 5

Sleeps
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Exceptional(12)

$312.98

/ Nightly
Condo

Malibu of the Midwest Condo steps from the Lake

Sheboygan, Wisconsin, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(12)

$321.43

/ Nightly
Private vacation home

Steps from Lake Michigan: North Point Place

Sheboygan, Wisconsin, United States

Bed 3

Bed

Bath 1

Bath

Sleep 7

Sleeps
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Exceptional(12)

$354.69

/ Nightly
Private vacation home

Cozy Corner Cottage| Beach Access & Historic Charm

Sheboygan, Wisconsin, United States

Bed 3

Bed

Bath 1

Bath

Sleep 7

Sleeps
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Exceptional(12)

$349.02

/ Nightly
Villa

Wandering Waves | Beachfront Lake Michigan Stay!

Sheboygan, Wisconsin, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps

Most Popular Cities in Wisconsin