Sheboygan, Wisconsin Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Sheboygan, Wisconsin on RentalSaver.com!

Sheboygan Rentals

From $385 per night (USD)
VRBO
Edgewater Villa: 4 Bedroom, Sleeps 14!
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Modern 4BR Courtyard Condo – Steps from the Beach in the "Malibu of the Midwest" Escape to Sheboygan, WI—a hidden gem o ...
From $385 per night (USD)
VRBO
From $263 per night (USD)
Expedia
Beachfront Paradise: King Suite - Sleeps 8!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Soak in Lake Michigan views from this 2BR/2BA beachside condo, just steps from the boardwalk, harbor, shops, and restaur ...
From $263 per night (USD)
Expedia
From $181 per night (USD)
VRBO
Pet-Friendly Sheboygan Home: 4 Mi to Lake Michigan
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Indulge in a fun-filled getaway when you stay at this 2-bed, 1-bath Wisconsin vacation rental! Boasting a colorful open ...
From $181 per night (USD)
VRBO
From $299 per night (USD)
Expedia
New King Park Beach Lookout Deluxe! 3BR Right at Lake!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Welcome to King Park Beach Lookout Deluxe! Experience the perfect family getaway with panoramic views of Lake Michigan, ...
From $299 per night (USD)
Expedia
From $493 per night (USD)
VRBO
Charming 4-bedroom house with WiFi and AC in lovely Sheboygan
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Unwind in this fabulous 1970's home with modern upgrades. This spacious 3700 SF retreat features 4 bedrooms (3 queen, ...
From $493 per night (USD)
VRBO
From $236 per night (USD)
VRBO
Steps from Lake Michigan: North Point Place
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Conveniently located for adventure and relaxation along the lakeshore and beyond, this historic home is steps away from ...
From $236 per night (USD)
VRBO
From $420 per night (USD)
VRBO
Luxury Lake Front Villa: Sleeps 12!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Experience the ultimate in luxury at this exquisite 4 bedroom lakefront vacation rental on Lake Michigan, just minutes f ...
From $420 per night (USD)
VRBO
From $167 per night (USD)
VRBO
Breezy Beach - 75 Steps to Lake Michigan!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to 𝐁𝐫𝐞𝐞𝐳𝐲 𝐁𝐞𝐚𝐜𝐡 by 𝐆𝐫𝐞𝐚𝐭 𝐋𝐚𝐤𝐞𝐬 𝐆𝐞𝐭𝐚𝐰𝐚𝐲𝐬! Take advantage of FLEXIBLE MONTHLY RENTAL ...
From $167 per night (USD)
VRBO
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VRBO
Shoreline Sanctuary - 4BR Villa w/ Lake Views, Beach Access & Sunsets
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Shoreline Sanctuary by Great Lakes Getaways! This stunning 4-bedroom, 3-bathroom beachfront villa on Lake Michigan offe ...
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VRBO
From $87 per night (USD)
VRBO
Wandering Waves - Beachfront Lake Michigan Stay!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Wandering Waves by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 202 ...
From $87 per night (USD)
VRBO
From $141 per night (USD)
VRBO
NEW! Indigo Waters- Steps to the sand! Sleeps 7! Book today!
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Indigo Waters by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2026. ...
From $141 per night (USD)
VRBO
From $154 per night (USD)
Expedia
Sunset Vista 2br in Sheboygan
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
This cozy vacation rental is a perfect place to relax and enjoy a getaway! From its warm and inviting fireplace, with co ...
From $154 per night (USD)
Expedia
From $426 per night (USD)
VRBO
Luxury Villa on Lake Michigan!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Welcome to the ideal place on Lake Michigan for a family beach getaway, wind surfing, fishing, bachelorette weekend, gol ...
From $426 per night (USD)
VRBO
From $653 per night (USD)
Expedia
Vacation Paradise: 4 Bedroom, Sleeps 14!
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Enjoy life on the shores of Lake Michigan in this luxury, courtyard condo. This two-story, 4 bedroom/3 bathroom get-away ...
From $653 per night (USD)
Expedia
From $130 per night (USD)
VRBO
Charming 2-bedroom condo with WiFi, AC in quaint Sheboygan
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This fantastic condo in Sheboygan offers two bedrooms with queen beds, perfect for a relaxing getaway. With amenities li ...
From $130 per night (USD)
VRBO
From $1267 per night (USD)
Expedia
Baronwood Oasis-Indoor Pool/Spa-Arcades-16beds-LUX
Bedrooms:
5
Bathrooms:
7
Sleeps:
16
🏡 Welcome to Baronwood Oasis – The Ultimate Family Escape - Sleeps 16 This is your moment to be the hero of your fam ...
From $1267 per night (USD)
Expedia
From $151 per night (USD)
VRBO
Lake Breeze on 11th
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Sheboygan has lots to offer & our place is perfect for your homebase. The lakefront, Sunrise, End, & Vollrath park are j ...
From $151 per night (USD)
VRBO
From $371 per night (USD)
VRBO
NEW! Charming 3BR/2BA Lake House in the Woods of the desirable Black River area
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Your much-needed retreat begins at this large 3-bedroom house 300-feet from Lake Michigan. This wonderful property featu ...
From $371 per night (USD)
VRBO
From $199 per night (USD)
VRBO
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Welcome to the Coastal Comfort! Comfort: noun - a state of physical ease and freedom from pain or constraint Come in a ...
From $199 per night (USD)
VRBO
From $163 per night (USD)
Expedia
Sheboygan Sunrise Beach Stay
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
*** STEPS AWAY FROM LAKE MICHIGAN*** Experience the vibrant energy from our stylish apartment with great views. Enjoy e ...
From $163 per night (USD)
Expedia
From $142 per night (USD)
VRBO
Overlook Oasis - Lakeside Stay in Ellis District
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to Overlook Oasis by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through Ap ...
From $142 per night (USD)
VRBO
From $136 per night (USD)
VRBO
2 Mi to Dtwn: Studio Suite in Sheboygan
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Pet Friendly w/ Fee | Walk to Diner & Brewery | Private Balcony Set sail for a getaway near the shore of Lake Michigan ...
From $136 per night (USD)
VRBO
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VRBO
Charming, Modern Riverfront 2-bedroom South Pier, Sheboygan Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Stay comfortably in Sheboygan at this 2-bedroom condo. The space features 2 lovely queen beds, 2 bathrooms with showers, ...
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VRBO
From $231 per night (USD)
Expedia
NEW! Harbor Hideaway - Walk to Beach, Dining & Downtown
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cozy Condo Steps from Sheboygan Harbor – Walk to Beach, Dining & Downtown Perfectly situated just steps from the Sheb ...
From $231 per night (USD)
Expedia
From $385 per night (USD)
VRBO
Edgewater Escape: 4 Bedroom, Sleeps 14!
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
This two-story 4 bedroom/3 bathroom get-away is in close proximity to EVERYTHING, including the boardwalk, harbor and do ...
From $385 per night (USD)
VRBO
From $623 per night (USD)
Expedia
Just Beachy: 4 Bedroom, Sleeps 12!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Newly Renovated 4BR/3BA Upper-Level Condo – Walk to Boardwalk, Harbor & More! Welcome to your perfect home away from ho ...
From $623 per night (USD)
Expedia
From $131 per night (USD)
VRBO
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Your cozy getaway awaits in Sheboygan at this beautiful upper unit duplex . This nice space features 1 bedroom with a co ...
From $131 per night (USD)
VRBO
From $483 per night (USD)
Expedia
Sheboygan Chalet | Nature, Arcade, Sauna & Hot Tub
Bedrooms:
3
Bathrooms:
4
Sleeps:
13
Escape to Sheboygan Chalet—a stunning modern retreat tucked in the woods of the Black River community 🌲 Just two blocks ...
From $483 per night (USD)
Expedia
From $496 per night (USD)
VRBO
4- Bedroom Retreat w/ Sauna, Game Room, Patio & Walk to Golf, Bars & Restaurants
Bedrooms:
2
Bathrooms:
4
Sleeps:
13
This newly renovated home offers the ultimate blend of comfort, fun, and convenience. Located in the heart of the city, ...
From $496 per night (USD)
VRBO
From $498 per night (USD)
Expedia
Fully renovated, updated, and high-end finished 5 bedroom facing the marina!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
No expense spared in this fully renovated, updated, and high-end finished home facing the water and a block from the bea ...
From $498 per night (USD)
Expedia
From $300 per night (USD)
VRBO
Pet-Friendly 3BR Retreat!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Relaxing 3-Bedroom Retreat Near Lake Michigan – Pet Friendly! Welcome to your perfect home base in Sheboygan! This spac ...
From $300 per night (USD)
VRBO
$Lake Breeze Cottage. \nOne block from the lake, walking distance to downtown!$
From $229 per night (USD)
Expedia
Lake Breeze Cottage. \nOne block from the lake, walking distance to downtown!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Lake Breeze Cottage, your year-round getaway just one block from the sparkling shores of Lake Michigan. Wheth ...
From $229 per night (USD)
Expedia
From $222 per night (USD)
VRBO
Large Backyard, Walk to Hospital: Sheboygan Abode!
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Mid-Term Stays & Travel Nurses Welcome | Near Fishing & Golf | WFH Friendly Whether you're here for work or play, you'l ...
From $222 per night (USD)
VRBO
From $140 per night (USD)
Expedia
Surfside Retreat – Walk to Lake
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Perfectly located near downtown Sheboygan and just one block from Lake Michigan, this home offers everything a traveler ...
From $140 per night (USD)
Expedia
From $136 per night (USD)
VRBO
Storybook 2-bedroom apartment 1mi from Lake Michigan
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to The Fox & Folly Inn —a unique whimsical retreat. Perfect for families and those who are kids at heart! • Cr ...
From $136 per night (USD)
VRBO
From $177 per night (USD)
Expedia
Sheboygan Riverside Condo
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Experience the Malibu of the Midwest in this stunning 2-bedroom retreat! The king suite offers a private balcony with a ...
From $177 per night (USD)
Expedia
From $181 per night (USD)
VRBO
The Beach town bungalow
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Cozy second-floor Airbnb in Sheboygan, WI, the “Malibu of the Midwest.” 2-bed, 1-bath with queen master, bunk room, full ...
From $181 per night (USD)
VRBO

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Sheboygan Rentals

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Results: 137 Rentals