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Sheboygan Vacation Rentals

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Bedrooms

Bathrooms

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Distance from

5 mi
138 rentals in Sheboygan.
Amazing downtown waterfront condo with full hook-up boat slip! Close to beach!, vacation rental in Sheboygan
Amazing downtown waterfront condo with full hook-up boat slip! Close to beach!, vacation rental in Sheboygan
Amazing downtown waterfront condo with full hook-up boat slip! Close to beach!, vacation rental in Sheboygan

Amazing downtown waterfront condo with full hook-up boat slip! Close to beach!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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Calling all Golfers, RA Enthusiasts, GB Packer fans, and Lake Mich lovers, vacation rental in Sheboygan
Calling all Golfers, RA Enthusiasts, GB Packer fans, and Lake Mich lovers, vacation rental in Sheboygan
Calling all Golfers, RA Enthusiasts, GB Packer fans, and Lake Mich lovers, vacation rental in Sheboygan

Calling all Golfers, RA Enthusiasts, GB Packer fans, and Lake Mich lovers

Condo/Apartment
2 bedrooms
0 bathrooms
Sleeps 2
Match: Sleeps
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Corner River Walk Condo with Spectacular Views, vacation rental in Sheboygan
Corner River Walk Condo with Spectacular Views, vacation rental in Sheboygan
Corner River Walk Condo with Spectacular Views, vacation rental in Sheboygan

Corner River Walk Condo with Spectacular Views

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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Beach front luxury specious condo/ villa !, vacation rental in Sheboygan
Beach front luxury specious condo/ villa !, vacation rental in Sheboygan
Beach front luxury specious condo/ villa !, vacation rental in Sheboygan

Beach front luxury specious condo/ villa !

Rental Home
4 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Malibu of the Midwest Condo steps from the Lake, vacation rental in Sheboygan
Malibu of the Midwest Condo steps from the Lake, vacation rental in Sheboygan
Malibu of the Midwest Condo steps from the Lake, vacation rental in Sheboygan

Malibu of the Midwest Condo steps from the Lake

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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Amazing interior remodel for 6 in quiet safe walkable central neighborhood, vacation rental in Sheboygan
Amazing interior remodel for 6 in quiet safe walkable central neighborhood, vacation rental in Sheboygan
Amazing interior remodel for 6 in quiet safe walkable central neighborhood, vacation rental in Sheboygan

Amazing interior remodel for 6 in quiet safe walkable central neighborhood

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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South Pier Riverwalk Condo-Steps from some of the best Sheboygan has to offer., vacation rental in Sheboygan
South Pier Riverwalk Condo-Steps from some of the best Sheboygan has to offer., vacation rental in Sheboygan
South Pier Riverwalk Condo-Steps from some of the best Sheboygan has to offer., vacation rental in Sheboygan

South Pier Riverwalk Condo-Steps from some of the best Sheboygan has to offer.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Directly on Lake Michigan! Last Minute Bookings Welcome!, vacation rental in Sheboygan
Directly on Lake Michigan! Last Minute Bookings Welcome!, vacation rental in Sheboygan
Directly on Lake Michigan! Last Minute Bookings Welcome!, vacation rental in Sheboygan

Directly on Lake Michigan! Last Minute Bookings Welcome!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Edgewater Escapes - 4 bed/3 bath w/ steps to Lake, vacation rental in Sheboygan
Edgewater Escapes - 4 bed/3 bath w/ steps to Lake, vacation rental in Sheboygan
Edgewater Escapes - 4 bed/3 bath w/ steps to Lake, vacation rental in Sheboygan

Edgewater Escapes - 4 bed/3 bath w/ steps to Lake

Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Lake Michigan home with gorgeous views, great spot for a family or golf retreat, vacation rental in Sheboygan
Lake Michigan home with gorgeous views, great spot for a family or golf retreat, vacation rental in Sheboygan
Lake Michigan home with gorgeous views, great spot for a family or golf retreat, vacation rental in Sheboygan

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

Rental Home
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
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Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home, vacation rental in Sheboygan
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home, vacation rental in Sheboygan
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home, vacation rental in Sheboygan

Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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BEST LOCATION IN SHEBOYGAN!  Steps to beach & marina, walk to historic downtown!, vacation rental in Sheboygan
BEST LOCATION IN SHEBOYGAN!  Steps to beach & marina, walk to historic downtown!, vacation rental in Sheboygan
BEST LOCATION IN SHEBOYGAN!  Steps to beach & marina, walk to historic downtown!, vacation rental in Sheboygan

BEST LOCATION IN SHEBOYGAN! Steps to beach & marina, walk to historic downtown!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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*NEW* Sleeps 8 & Spacious!, vacation rental in Sheboygan
*NEW* Sleeps 8 & Spacious!, vacation rental in Sheboygan
*NEW* Sleeps 8 & Spacious!, vacation rental in Sheboygan

*NEW* Sleeps 8 & Spacious!

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub, vacation rental in Sheboygan
2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub, vacation rental in Sheboygan
2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub, vacation rental in Sheboygan

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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4 Bedroom Home on the River with Private River access, vacation rental in Sheboygan
4 Bedroom Home on the River with Private River access, vacation rental in Sheboygan
4 Bedroom Home on the River with Private River access, vacation rental in Sheboygan

4 Bedroom Home on the River with Private River access

Rental Home
4 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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BEST LOCATION IN SHEBOYGAN!  Steps to beach & marina, walk to historic downtown!, vacation rental in Sheboygan
BEST LOCATION IN SHEBOYGAN!  Steps to beach & marina, walk to historic downtown!, vacation rental in Sheboygan
BEST LOCATION IN SHEBOYGAN!  Steps to beach & marina, walk to historic downtown!, vacation rental in Sheboygan

BEST LOCATION IN SHEBOYGAN! Steps to beach & marina, walk to historic downtown!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Beach and Golf House, vacation rental in Sheboygan
Beach and Golf House, vacation rental in Sheboygan
Beach and Golf House, vacation rental in Sheboygan

Beach and Golf House

Rental Home
4 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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4 Bedroom Beachfront Condo, vacation rental in Sheboygan
4 Bedroom Beachfront Condo, vacation rental in Sheboygan
4 Bedroom Beachfront Condo, vacation rental in Sheboygan

4 Bedroom Beachfront Condo

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Over 1600 sq ft overlooking Sheboygan's Riverfront District right on the water., vacation rental in Sheboygan
Over 1600 sq ft overlooking Sheboygan's Riverfront District right on the water., vacation rental in Sheboygan
Over 1600 sq ft overlooking Sheboygan's Riverfront District right on the water., vacation rental in Sheboygan

Over 1600 sq ft overlooking Sheboygan's Riverfront District right on the water.

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
More info
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*NEW* Beautiful & Convenient!, vacation rental in Sheboygan
*NEW* Beautiful & Convenient!, vacation rental in Sheboygan
*NEW* Beautiful & Convenient!, vacation rental in Sheboygan

*NEW* Beautiful & Convenient!

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
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BEACHSIDE GETAWAY, vacation rental in Sheboygan
BEACHSIDE GETAWAY, vacation rental in Sheboygan
BEACHSIDE GETAWAY, vacation rental in Sheboygan

BEACHSIDE GETAWAY

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Affiliated with FlipKey
Riverfront Townhome with Breathtaking Water Views!, vacation rental in Sheboygan
Riverfront Townhome with Breathtaking Water Views!, vacation rental in Sheboygan
Riverfront Townhome with Breathtaking Water Views!, vacation rental in Sheboygan

Riverfront Townhome with Breathtaking Water Views!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Walk to beach, restaurants, shops! Historic charm with updated amenities, vacation rental in Sheboygan
Walk to beach, restaurants, shops! Historic charm with updated amenities, vacation rental in Sheboygan
Walk to beach, restaurants, shops! Historic charm with updated amenities, vacation rental in Sheboygan

Walk to beach, restaurants, shops! Historic charm with updated amenities

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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The River Bed - Condo sleeps 4 on west side, vacation rental in Sheboygan
The River Bed - Condo sleeps 4 on west side, vacation rental in Sheboygan
The River Bed - Condo sleeps 4 on west side, vacation rental in Sheboygan

The River Bed - Condo sleeps 4 on west side

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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REMODELED HOME ON LAKE MICHIGAN, vacation rental in Sheboygan
REMODELED HOME ON LAKE MICHIGAN, vacation rental in Sheboygan
REMODELED HOME ON LAKE MICHIGAN, vacation rental in Sheboygan

REMODELED HOME ON LAKE MICHIGAN

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city, vacation rental in Sheboygan
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city, vacation rental in Sheboygan
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city, vacation rental in Sheboygan

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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Luxury Downtown Sheboygan 4 Bdr on Lake Michigan Beach, vacation rental in Sheboygan
Luxury Downtown Sheboygan 4 Bdr on Lake Michigan Beach, vacation rental in Sheboygan
Luxury Downtown Sheboygan 4 Bdr on Lake Michigan Beach, vacation rental in Sheboygan

Luxury Downtown Sheboygan 4 Bdr on Lake Michigan Beach

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
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Riverfront Townhome with GIANT Rec Room and Private Riverfront Deck, vacation rental in Sheboygan
Riverfront Townhome with GIANT Rec Room and Private Riverfront Deck, vacation rental in Sheboygan
Riverfront Townhome with GIANT Rec Room and Private Riverfront Deck, vacation rental in Sheboygan

Riverfront Townhome with GIANT Rec Room and Private Riverfront Deck

Rental Home
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Downtown Sheboygan Charmer!, vacation rental in Sheboygan
Downtown Sheboygan Charmer!, vacation rental in Sheboygan
Downtown Sheboygan Charmer!, vacation rental in Sheboygan

Downtown Sheboygan Charmer!

Rental Home
5 bedrooms
1 bathroom
Sleeps 9
Match: Sleeps
More info
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Private Guest Room 2E - East Room Close to Lake Michigan , vacation rental in Sheboygan
Private Guest Room 2E - East Room Close to Lake Michigan , vacation rental in Sheboygan
Private Guest Room 2E - East Room Close to Lake Michigan , vacation rental in Sheboygan

Private Guest Room 2E - East Room Close to Lake Michigan

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Affiliated with FlipKey
Dog-friendly centrally located townhouse on the Sheboygan River., vacation rental in Sheboygan
Dog-friendly centrally located townhouse on the Sheboygan River., vacation rental in Sheboygan
Dog-friendly centrally located townhouse on the Sheboygan River., vacation rental in Sheboygan

Dog-friendly centrally located townhouse on the Sheboygan River.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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BEST LOCATION IN SHEBOYGAN! Watch the sunrise over Lake Michigan Steps to beach., vacation rental in Sheboygan
BEST LOCATION IN SHEBOYGAN! Watch the sunrise over Lake Michigan Steps to beach., vacation rental in Sheboygan
BEST LOCATION IN SHEBOYGAN! Watch the sunrise over Lake Michigan Steps to beach., vacation rental in Sheboygan

BEST LOCATION IN SHEBOYGAN! Watch the sunrise over Lake Michigan Steps to beach.

Rental Home
3 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Stunning 4-Bedroom Lakefront Condo - Your Perfect Escape!, vacation rental in Sheboygan
Stunning 4-Bedroom Lakefront Condo - Your Perfect Escape!, vacation rental in Sheboygan
Stunning 4-Bedroom Lakefront Condo - Your Perfect Escape!, vacation rental in Sheboygan

Stunning 4-Bedroom Lakefront Condo - Your Perfect Escape!

Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Riverfront Sheboygan Townhome w/ Fire Pit!, vacation rental in Sheboygan
Riverfront Sheboygan Townhome w/ Fire Pit!, vacation rental in Sheboygan
Riverfront Sheboygan Townhome w/ Fire Pit!, vacation rental in Sheboygan

Riverfront Sheboygan Townhome w/ Fire Pit!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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3 Bedroom Beach House, vacation rental in Sheboygan
3 Bedroom Beach House, vacation rental in Sheboygan
3 Bedroom Beach House, vacation rental in Sheboygan

3 Bedroom Beach House

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Conveniently located in beautiful Sheboygan!, vacation rental in Sheboygan
Conveniently located in beautiful Sheboygan!, vacation rental in Sheboygan
Conveniently located in beautiful Sheboygan!, vacation rental in Sheboygan

Conveniently located in beautiful Sheboygan!

Rental Home
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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REMODELED HOME OVERLOOKING LAKE MICHIGAN, vacation rental in Sheboygan
REMODELED HOME OVERLOOKING LAKE MICHIGAN, vacation rental in Sheboygan
REMODELED HOME OVERLOOKING LAKE MICHIGAN, vacation rental in Sheboygan

REMODELED HOME OVERLOOKING LAKE MICHIGAN

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Affiliated with FlipKey
Newly updated flat 1 block from Lake Michigan; Lake View; Watch sun rise!, vacation rental in Sheboygan
Newly updated flat 1 block from Lake Michigan; Lake View; Watch sun rise!, vacation rental in Sheboygan
Newly updated flat 1 block from Lake Michigan; Lake View; Watch sun rise!, vacation rental in Sheboygan

Newly updated flat 1 block from Lake Michigan; Lake View; Watch sun rise!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Cozy 2 bd home, minutes from lake Michigan, vacation rental in Sheboygan
Cozy 2 bd home, minutes from lake Michigan, vacation rental in Sheboygan
Cozy 2 bd home, minutes from lake Michigan, vacation rental in Sheboygan

Cozy 2 bd home, minutes from lake Michigan

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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2 Bedroom, 1 bath apartment, vacation rental in Sheboygan
2 Bedroom, 1 bath apartment, vacation rental in Sheboygan
2 Bedroom, 1 bath apartment, vacation rental in Sheboygan

2 Bedroom, 1 bath apartment

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Cute Quiet Neighborhood Hideway, vacation rental in Sheboygan
Cute Quiet Neighborhood Hideway, vacation rental in Sheboygan
Cute Quiet Neighborhood Hideway, vacation rental in Sheboygan

Cute Quiet Neighborhood Hideway

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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3 blocks from Lake Spacious  Entire Place 1 BDRM full bath 5 min to downtown, vacation rental in Sheboygan
3 blocks from Lake Spacious  Entire Place 1 BDRM full bath 5 min to downtown, vacation rental in Sheboygan
3 blocks from Lake Spacious  Entire Place 1 BDRM full bath 5 min to downtown, vacation rental in Sheboygan

3 blocks from Lake Spacious Entire Place 1 BDRM full bath 5 min to downtown

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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This location is13 minutes from 2020 Ryder cup at Whistling straights.  It's 2, vacation rental in Sheboygan
This location is13 minutes from 2020 Ryder cup at Whistling straights.  It's 2, vacation rental in Sheboygan
This location is13 minutes from 2020 Ryder cup at Whistling straights.  It's 2, vacation rental in Sheboygan

This location is13 minutes from 2020 Ryder cup at Whistling straights. It's 2

Rental Home
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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3 Bedroom lower unit -Brand New Remodel, vacation rental in Sheboygan
3 Bedroom lower unit -Brand New Remodel, vacation rental in Sheboygan
3 Bedroom lower unit -Brand New Remodel, vacation rental in Sheboygan

3 Bedroom lower unit -Brand New Remodel

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Corporate Travelers, vacation rental in Sheboygan
Corporate Travelers, vacation rental in Sheboygan
Corporate Travelers, vacation rental in Sheboygan

Corporate Travelers

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Sheboygan Marina 2br Upper Unit. Close to beach and boat launch., vacation rental in Sheboygan
Sheboygan Marina 2br Upper Unit. Close to beach and boat launch., vacation rental in Sheboygan
Sheboygan Marina 2br Upper Unit. Close to beach and boat launch., vacation rental in Sheboygan

Sheboygan Marina 2br Upper Unit. Close to beach and boat launch.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Cottage in the Woods walk to Lake Michigan!, vacation rental in Sheboygan
Cottage in the Woods walk to Lake Michigan!, vacation rental in Sheboygan
Cottage in the Woods walk to Lake Michigan!, vacation rental in Sheboygan

Cottage in the Woods walk to Lake Michigan!

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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2BR Duplex Lower Overlooking Kiwanis Park, vacation rental in Sheboygan
2BR Duplex Lower Overlooking Kiwanis Park, vacation rental in Sheboygan
2BR Duplex Lower Overlooking Kiwanis Park, vacation rental in Sheboygan

2BR Duplex Lower Overlooking Kiwanis Park

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Scenic Lake Views in Sheboygan, vacation rental in Sheboygan
Scenic Lake Views in Sheboygan, vacation rental in Sheboygan
Scenic Lake Views in Sheboygan, vacation rental in Sheboygan

Scenic Lake Views in Sheboygan

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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BEACHSIDE GETAWAY IN SHEBOYAN, vacation rental in Sheboygan
BEACHSIDE GETAWAY IN SHEBOYAN, vacation rental in Sheboygan
BEACHSIDE GETAWAY IN SHEBOYAN, vacation rental in Sheboygan

BEACHSIDE GETAWAY IN SHEBOYAN

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Showing results 1-50 of 138
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