Vacation Home Rentals By Owner In Sheboygan, WI

Showing 40 Of 64 Vacation Rentals

Exceptional(23)

$183.6

/ Nightly

Private Vacation Home

Lake Breeze on 11th

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$324.94

/ Nightly

Private Vacation Home

9 Mi to Shore: Home w/ Hot Tub in Howards Grove!

Howards Grove, Wisconsin, United States

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Bath

Sleeps

Exceptional(2)

$396.69

/ Nightly

Private Vacation Home

Pet-Friendly 3BR Retreat!

Sheboygan, Wisconsin, United States

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Bath

Sleeps

Exceptional(17)

$473.17

/ Nightly

Private Vacation Home

Spacious Sheboygan Home w/ Grill & Fire Pit!

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(14)

$616.31

/ Nightly

Private Vacation Home

The Links! - Luxury Golf Retreat with Golf Simulator

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(1)

$711.65

/ Nightly

Private Vacation Home

Luxury Pool Retreat - 2 Acres - Near Whistling Straits

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

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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

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Bath

Sleeps

Exceptional(12)

$1352.93

/ Nightly

Private Vacation Home

Baronwood Oasis | Pool + Arcade Mega Estate

Sheboygan, Wisconsin, United States

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Bath

Sleeps

Exceptional(9)

$1977.17

/ Nightly

Private Vacation Home

Fairway Getaway-by Whistling Straits, Golf sim/Theater Room, ZenDen &Poker Room!

Sheboygan, Wisconsin, United States

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Bath

Sleeps

$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(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)

$177.63

/ Nightly

Private Vacation Home

LUX Uptown Escape - The Trester

Sheboygan, Wisconsin, United States

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Bath

Sleeps

Exceptional(19)

$181.6

/ Nightly

Private Vacation Home

3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(28)

$192.96

/ Nightly

Private Vacation Home

Dog-Friendly Sheboygan Home - 1 Mi to Town!

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(266)

$205.16

/ Nightly

Private Vacation Home

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

Sheboygan, Wisconsin, United States

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Bath

Sleeps

Exceptional(3)

$228.14

/ Nightly

Private Vacation Home

Fresh Coast Craftsman - Pet Friendly | Near Lake

Sheboygan, Wisconsin, United States

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Bath

Sleeps

Exceptional(8)

$238.36

/ Nightly

Private Vacation Home

Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(3)

$245.17

/ Nightly

Private Vacation Home

At River's Edge | 2BR River Retreat with Garage

Sheboygan, Wisconsin, United States

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Bath

Sleeps

Rent a place that suits your needs

Condo

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Private vacation home

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Most popular vacation rentals in Sheboygan

Exceptional(3)

$327.49

/ Nightly

Cottage

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

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(3)

$277.99

/ Nightly

Condo

Beachside Condo Downtown with Lake Michigan Views

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(3)

$289.43

/ Nightly

Private vacation home

REMODELED HOME ON LAKE MICHIGAN

Sheboygan, Wisconsin, United States

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Bath

Sleeps

Exceptional(3)

$301.91

/ Nightly

Private vacation home

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

Sheboygan, Wisconsin, United States

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Bath

Sleeps

Exceptional(3)

$302.48

/ Nightly

Condo

The Cottage | Beachfront Condo on Lake Michigan

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(3)

$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(3)

$312.98

/ Nightly

Condo

Malibu of the Midwest Condo steps from the Lake

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(3)

$321.43

/ Nightly

Private vacation home

Steps from Lake Michigan: North Point Place

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(3)

$354.69

/ Nightly

Private vacation home

Cozy Corner Cottage| Beach Access & Historic Charm

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(3)

$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

$183.6

$324.94

$396.69

$473.17

$616.31

$640.71

$711.65

$999.86

$1003.84

$1352.93

$1977.17

$2164.67

$341.64

$177.63

$181.6

$192.96

$205.16

$228.14

$238.36

$245.17

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