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

Sheboygan Rentals

From $243 per night (USD)
VRBO
3 Bedroom Beach House
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Three-bedroom house with full kitchen, dining room with spacious living room to watch movies, relax, play board games an ...
From $243 per night (USD)
VRBO
From $227 per night (USD)
Expedia
REMODELED HOME ON LAKE MICHIGAN
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
3 Bedrooms and 1.5 Baths in this two-story brick home. Located about one mile south of downtown Sheboygan on a bluff ove ...
From $227 per night (USD)
Expedia
From $435 per night (USD)
VRBO
5 Bedroom Modern House
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
5 bedroom modern home. Full kitchen includes dishwasher, microwave, stove, fridge, keurig, everyday utensils and pans. P ...
From $435 per night (USD)
VRBO
From $261 per night (USD)
VRBO
Updated Sheboygan Home w/ Porch < 1 Mi to Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
100
Discover contemporary comfort right beside Lake Michigan’s coast with a trip to this 3-bedroom, 2-bathroom Sheboygan vac ...
From $261 per night (USD)
VRBO
$Seagull Beach Guest House, Unique Lake Michigan Cottage\non private beach$
From $230 per night (USD)
VRBO
Seagull Beach Guest House, Unique Lake Michigan Cottage\non private beach
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
The whimsical little cottage has a spectacular view of the private beach, the woods and sunrises. Starting right at your ...
From $230 per night (USD)
VRBO
From $163 per night (USD)
VRBO
The River Bed - Condo sleeps 4 on west side
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
5 minutes from Kohler & minutes from world class champion golf courses! Brand new & clean! Just completed condo with 2 ...
From $163 per night (USD)
VRBO
From $419 per night (USD)
VRBO
Family Home, 1 Block to Lake Michigan Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
- Game Room - Central Location - Recently Remodeled From Lake Michigan to downtown, there's something for everyone at t ...
From $419 per night (USD)
VRBO
From $1283 per night (USD)
Expedia
Quiet and spacious home, close to downtown, the beach, and fantastic golfing.
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Nestled on a wooded acre in a quiet cul de sac. The cozy wood burning fireplace and wet bar in the family room is great ...
From $1283 per night (USD)
Expedia
$Beach Lake House walking disance to lake Close to Downtown\n & South Pier\n4BR 2BA$
From $563 per night (USD)
VRBO
Beach Lake House walking disance to lake Close to Downtown\n & South Pier\n4BR 2BA
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Amazing location just 3 blocks of Lake Michigan. a short walk to the public south beach, 2 min driving to the beach. 4 ...
From $563 per night (USD)
VRBO
From $181 per night (USD)
VRBO
Good Vibes on the Third Coast-Pet Friendly! Cozy and Close by!
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
Peaceful bohemian retreat filled with warmth and a lively vibe! Perfect for couples, remote workers, girls weekends, gol ...
From $181 per night (USD)
VRBO
Click For Pricing
VRBO
Modern Cabin, private wooded lot with lake access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Newly renovated home with grilling deck and fire pit. 600 foot walk to the beach. Brand new Kohler bathrooms, electric f ...
Click For Pricing
VRBO
From $222 per night (USD)
Expedia
2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Modern/updated 2 bedroom 2 bath townhouse on a quite Cul-De-Sac in Sheboygan, WI. Every part of this house has been remo ...
From $222 per night (USD)
Expedia
From $1986 per night (USD)
VRBO
Don’t be a turkey – Celebrate Thanksgiving with family all under one roof.
Bedrooms:
7
Bathrooms:
10
Sleeps:
24
The 10,000 square foot Castino Lakeview Mansion sits high atop a bluff with uninterrupted breathtaking views of Lake Mic ...
From $1986 per night (USD)
VRBO
From $1424 per night (USD)
VRBO
Shoreline Sanctuary - 4 Bedroom Beachfront Condo
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Welcome to your perfect getaway at Shoreline Sanctuary! This beautifully updated and meticulously maintained condo is a ...
From $1424 per night (USD)
VRBO
From $676 per night (USD)
VRBO
Lake Michigan Home with gorgeous views, great spot for family or golf retreat
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Our beautiful lakefront home is perfect for a relaxing retreat! Minutes to downtown Sheboygan, downtown Kohler with 5 ...
From $676 per night (USD)
VRBO
Click For Pricing
Expedia
Ryder Cup - Premier Location!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This newly remodeled and professionally cleaned home is 8 minutes from Whistling Straits and within walking distance to ...
Click For Pricing
Expedia
From $347 per night (USD)
VRBO
Art Collector’s Dream • Remodeled Masterpiece with Gallery Vibes
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Newly renovated 1904 home in prime location. Remodeled kitchen and baths, gorgeous woodwork and floors, off-street parki ...
From $347 per night (USD)
VRBO
From $402 per night (USD)
Expedia
Beach and Golf House
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
This home is in the perfect location to explore everything Sheboygan County has to offer. It is located in the historic ...
From $402 per night (USD)
Expedia
From $141 per night (USD)
VRBO
2BR, 1.5BA, Pet-friendly, Lower duplex w/finished basement + large backyard!
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
This 2 bedroom, 2 bath lower duplex is the perfect spot to stay! It's just 3 short blocks to all of the restaurants of S ...
From $141 per night (USD)
VRBO
From $315 per night (USD)
Expedia
Classic brick charmer close to lake, river, and downtown!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Our classic 3 bedroom, 1 bathroom brick home located in the Historic Ellis District is central to the best experiences i ...
From $315 per night (USD)
Expedia
From $232 per night (USD)
VRBO
2BR Spacious Upper, Overlooking Kiwanis Park, Close to Everything!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This an Upstairs Duplex with 2 bedrooms and 1 bath. Features a kitchen stocked with pots, pans, utensils, and kitchen ga ...
From $232 per night (USD)
VRBO
From $187 per night (USD)
Expedia
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Kohler Design Center Rentals, Kohler Andrae State Park Rentals, Whistling Straits Rentals Blue Harbor Rentals, Road Amer ...
From $187 per night (USD)
Expedia
From $306 per night (USD)
VRBO
Wonderful 3+ Bedroom Home Completely Renovated
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Beautiful home in Sheboygan WI. Entire home has been completely remodeled and updated. Three entire floors of space fo ...
From $306 per night (USD)
VRBO
From $308 per night (USD)
Expedia
Updated Victorian in the Heart of Sheboygan. Beach, Downtown, Golf, Road America
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Lovingly restored 1890s Victorian home, updated to include the modern amenities you expect. Fully stocked kitchen, with ...
From $308 per night (USD)
Expedia
Click For Pricing
VRBO
Ryder Cup 2021 - Home near Lake Michigan, 6 miles from Whistling Straits
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
This mid-century modern home is situated in a quiet north Sheboygan Neighborhood, a 2 min walk to the Lake Michigan shor ...
Click For Pricing
VRBO
From $150 per night (USD)
Expedia
BEST LOCATION IN SHEBOYGAN! Steps to beach & marina, walk to historic downtown!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
My husband and I love to stay in a reasonably priced condo or flat when we travel. We like to feel like we are at a home ...
From $150 per night (USD)
Expedia
Click For Pricing
VRBO
10 min drive to Whistling Straits Golf course
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
4 bedroom House with 2.5 baths and finished basement. Lots of extra room to spread out or add air mattresses to accommod ...
Click For Pricing
VRBO
From $274 per night (USD)
Expedia
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Escape to this spacious downtown riverfront retreat with easy access to nearby beaches, restaurants, and local shopping ...
From $274 per night (USD)
Expedia
From $231 per night (USD)
VRBO
Scenic Lake Views in Sheboygan
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Watch the sun/moon come up over Lake Michigan across from the Sheboygan Marina and scenic lighthouse in this beautifully ...
From $231 per night (USD)
VRBO
From $349 per night (USD)
VRBO
Pet-Friendly Sheboygan Home, 1 Mi to Lake Michigan
Bedrooms:
1
Bathrooms:
4
Sleeps:
10
Whether you’re on the hunt for some good cheese, a delicious fried brat or just a simple lake retreat, this vacation ren ...
From $349 per night (USD)
VRBO
Click For Pricing
VRBO
Fun family home near Ryder Cup
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Minutes from Ryder Cup, steps from Lake Michigan. 4 bedroom home with open concept family room, kitchen, and formal dini ...
Click For Pricing
VRBO
From $827 per night (USD)
Expedia
Central located. Seconds from the highway to get to kohler, and Elkhart lake
Bedrooms:
2
Bathrooms:
4
Sleeps:
14
Everything you need on one level. complete modern Open concept living room, kitchen and dinning area. Hosts two large k ...
From $827 per night (USD)
Expedia
From $202 per night (USD)
VRBO
2BR Duplex Lower Overlooking Kiwanis Park
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This 2BR lower unit of a duplex is located in a quiet neighborhood, yet it is within walking distance of 2 coffee shops, ...
From $202 per night (USD)
VRBO
Click For Pricing
Expedia
Northside Charmer!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Charming Northside Sheboygan home just 5 miles from Whistling Straits, a ten minute walk to Lake Michigan and 15 minute ...
Click For Pricing
Expedia
From $198 per night (USD)
VRBO
BEACHSIDE GETAWAY IN SHEBOYGAN
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Located just one lot in from the beautiful shores or Lake Michigan. This amazing location provides year round stunning v ...
From $198 per night (USD)
VRBO
Click For Pricing
Expedia
Beautiful Historic Home Near Lake Michigan
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Beautiful historic home near Lake Michigan, only 6 blocks away. This house offers 4 bedrooms, 2 full bathrooms dinning ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Perfect location for Ryder Cup!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Tri-level home in a quiet neighborhood with modern updates and less than five miles from the Ryder Cup! Perfect backyard ...
Click For Pricing
VRBO
From $404 per night (USD)
Expedia
BEACHVIEW GETAWAY
Bedrooms:
1
Bathrooms:
5
Sleeps:
10
Amazing location just off of Lake Michigan. A quick walk to the public beach across the street or downtown as well. Prev ...
From $404 per night (USD)
Expedia
Click For Pricing
VRBO
16 MIN FROM RYDERCUP Wooded Retreat
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
3000 sq ft ranch 16 minutes from the Ryder Cup, this lovely 4 bed/2 bath is nestled in a beautiful wooded neighborhood a ...
Click For Pricing
VRBO
From $191 per night (USD)
Expedia
Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Whether you're here to visit friends or family, this lower-level 2-bed, 1-bath Sheboygan vacation rental apartment has a ...
From $191 per night (USD)
Expedia
From $277 per night (USD)
VRBO
Malibu of the Midwest Condo steps from the Lake
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
7th Heaven Condo is in the popular South Pier district. Cute condo is on the 2nd floor with elevator access. Across the ...
From $277 per night (USD)
VRBO
From $199 per night (USD)
Expedia
Logan Ave Holiday House - Upper
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Unique attractions and endless days by Lake Michigan await at this ideally located vacation rental! Hosting 2 bedrooms, ...
From $199 per night (USD)
Expedia
From $346 per night (USD)
VRBO
Beach front luxury spacious villa !
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Beach front luxury spacious condo! Beautiful remodeled four bedroom villa/condo overlooking Lake Michigan, well equippe ...
From $346 per night (USD)
VRBO
From $262 per night (USD)
Expedia
4 Bedroom Home on the River with Private River access
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Take in the coastal vibes as you enjoy your stay at this Riverfront home. With private access to the river, kayaks to us ...
From $262 per night (USD)
Expedia
From $364 per night (USD)
VRBO
LUXE Manor with Modern, Elegant Vibes
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Modern chic blends with classic sophistication in this late 1800s Manor. Enjoy the expansive 4,500 square feet of elegan ...
From $364 per night (USD)
VRBO
From $494 per night (USD)
VRBO
Modern Lakeside House with Treehouse
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
Welcome to Curtiss Castle! Ideal for large families, remote workers, lake lovers, and golf enthusiasts! This peaceful, w ...
From $494 per night (USD)
VRBO
Click For Pricing
VRBO
Top Floor Condo With Lake Michigan Views Throughout!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Relax in this luxurious new construction condo! Enjoy top floor Lake Michigan Views from every room! Balcony with lots o ...
Click For Pricing
VRBO
From $355 per night (USD)
Expedia
*NEW* Sleeps 8 & Spacious!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Superior Commons by Doorway Travel! This newly renovated and professionally decorated apartment is centrally ...
From $355 per night (USD)
Expedia
From $318 per night (USD)
VRBO
Newly Updated! Downtown & Shore
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to Superior Commons by Doorway Travel! This newly renovated and professionally decorated apartment is centrally ...
From $318 per night (USD)
VRBO
From $324 per night (USD)
Expedia
*NEW* Beautiful & Convenient!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to Superior Commons by Doorway Travel! This newly renovated and professionally decorated apartment is centrally ...
From $324 per night (USD)
Expedia
From $552 per night (USD)
VRBO
A Glorious Getaway Sheboygan - LUX Lake Condo
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Summary: Welcome to a Glorious Getaway! Steps to Lake Michigan come and enjoy this luxury 4 bed 3 bath condo. Located i ...
From $552 per night (USD)
VRBO
From $220 per night (USD)
Expedia
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to the Relax ‘n Retreat! Retreat: noun - a quiet or secluded place in which one can rest and relax Unwind at o ...
From $220 per night (USD)
Expedia
From $313 per night (USD)
VRBO
Perfect Paradise - Lakeview Condo w/ 7 Beds, Jacuzzi, and Balcony
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Perfect Paradise by Great Lakes Getaways! Unwind in this spacious 4-bedroom, 3-bath beachfront condo—perfect for famili ...
From $313 per night (USD)
VRBO
From $333 per night (USD)
VRBO
Peaceful Retreat, Near Road America! Mid Century Modern Home
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Peaceful and private getaway in the woods, yet close to everything! Shops, restaurants, bars, parks, golf, fishing, sail ...
From $333 per night (USD)
VRBO
From $310 per night (USD)
VRBO
Sheboygan Getaway w/ Deck + On-Site Lake Access!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Plan for plenty of outdoor fun on your next Lake Michigan getaway when you stay at this Sheboygan vacation rental! With ...
From $310 per night (USD)
VRBO
From $119 per night (USD)
Expedia
3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Place is all for you! No share place. Forget your worries in this spacious and serene Guest House ( sleeps 4 people) q ...
From $119 per night (USD)
Expedia
From $159 per night (USD)
VRBO
Sleeps 7{SPACIOUS}Pets Welcome!
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Welcome to Superior Commons by Doorway Travel! This newly renovated and professionally decorated apartment is centrally ...
From $159 per night (USD)
VRBO
$LUX Uptown Escape - The Trester\n$
From $179 per night (USD)
Expedia
LUX Uptown Escape - The Trester\n
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to our beautiful 2-bedroom historic home in Uptown Sheboygan! This charming and well-appointed residence offers ...
From $179 per night (USD)
Expedia
From $126 per night (USD)
VRBO
Cute Quiet Neighborhood Hideway
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Step back in time and relax in this 1930’s bungalow. Situated on the south side of the City of Sheboygan, able to feel t ...
From $126 per night (USD)
VRBO
From $742 per night (USD)
VRBO
Luxurious artistic 2 bed - 2 bath Condo; feel like living by the Coast!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This is a very well-taken care of condo in the most touristic part of Sheboygan. Be close to two beaches, a pier walk, a ...
From $742 per night (USD)
VRBO
From $222 per night (USD)
VRBO
The Cottage - Newly Renovated Beachfront Condo on Lake Michigan
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
The Cottage by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2026. ...
From $222 per night (USD)
VRBO
From $426 per night (USD)
Expedia
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
Bedrooms:
2
Bathrooms:
4
Sleeps:
11
Enjoy your Sheboygan getaway in this spacious 4-bedroom, 2-bath home just a 5-minute walk to the lake. Sleeps 11 and pac ...
From $426 per night (USD)
Expedia
From $145 per night (USD)
VRBO
Lovely Lake Lookout - Cozy 2BR Condo Steps from Lake Michigan
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Lovely Lake Lookout by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, ...
From $145 per night (USD)
VRBO
From $241 per night (USD)
Expedia
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Nestled in the heart of Sheboygan, our location is a true gem! We are just steps away from the shores of Lake Michigan a ...
From $241 per night (USD)
Expedia
$Pelican Point - Private Retreat - just 4 miles to downtown Sheboygan\n$
From $1230 per night (USD)
VRBO
Pelican Point - Private Retreat - just 4 miles to downtown Sheboygan\n
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Escape to your own private Lakeside Retreat. 4 BR, 2.5 bath Cape Cod overlooking Lake Michigan & Black River giving you ...
From $1230 per night (USD)
VRBO
From $177 per night (USD)
Expedia
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
About this space: Renovated 1930's home located in the historic downtown district within walking distance of breathtakin ...
From $177 per night (USD)
Expedia
Click For Pricing
VRBO
Spacious Blue Harbor 2 bedr courtyard view condo w/ Breaker Bay Waterpark access
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Detach yourself from the main crowd and check yourself into the 1242 square feet of spacious privacy of your own lakesid ...
Click For Pricing
VRBO
From $1167 per night (USD)
Expedia
Fairway Getaway-by Whistling Straits, Golf sim/Theater Room, ZenDen &Poker Room!
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Welcome to Fairway Getaway! This stunning property combines luxury, comfort, and convenience, making it the perfect choi ...
From $1167 per night (USD)
Expedia
From $136 per night (USD)
VRBO
Cozy and private 3 bedroom unit located a few blocks from downtown Sheboygan.
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Located just a couple blocks from downtown Sheboygan! Visit the shops and unique restaurants just a short walk away, or ...
From $136 per night (USD)
VRBO
From $134 per night (USD)
Expedia
Urban Lake Condo in Sheboygan's Historic Ellis District
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Your family will be within walking distance of almost everything when you stay at this centrally-located harborside gem ...
From $134 per night (USD)
Expedia
From $255 per night (USD)
VRBO
Riverwalk Retreat - Riverfront 3BR Condo w/ Jacuzzi & Lake Michigan Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Riverwalk Retreat by Great lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2 ...
From $255 per night (USD)
VRBO
From $74 per night (USD)
VRBO
Lakeside Condo - 2BR, Lake Michigan Views & Massage Chair
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Crystal Cove by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2026. ...
From $74 per night (USD)
VRBO
From $262 per night (USD)
VRBO
Lighthouse Lookout - 3BR / Steps to Lake Michigan & Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Lighthouse Lookout by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, ...
From $262 per night (USD)
VRBO
$\n\nLuxury Downtown Sheboygan 4BR-2.5 Bath - 3 min walk to beach - Lakeside Legacy$
From $766 per night (USD)
Expedia
\n\nLuxury Downtown Sheboygan 4BR-2.5 Bath - 3 min walk to beach - Lakeside Legacy
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Grand colonial meets coastal luxe in this 2800 square ft, 4 bedroom home along the magnificent Lake Michigan coast. Stun ...
From $766 per night (USD)
Expedia
From $552 per night (USD)
VRBO
Luxury Lake House-4Bed-2Bath-NEW Renovation 2023-Walk to Beach, Dining, & More.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Luxury Modern Farmhouse 4B-2Ba Lake & Beach House! Is it time for a Cool Change? Relax and rejuvenate at Sheboygan's n ...
From $552 per night (USD)
VRBO
From $158 per night (USD)
Expedia
Downtown, Uniquely Designed, Near the Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to the Uptown Coach House, hosted by Sheboygan Vacation Rentals. Our newly built coach house is nestled in the ...
From $158 per night (USD)
Expedia
From $355 per night (USD)
VRBO
State Park w/ Orchard Style Yard & Pavilion
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to our Orchard House Retreat, hosted by Sheboygan Vacation Rentals. Our home is situated directly across from t ...
From $355 per night (USD)
VRBO
From $186 per night (USD)
VRBO
Cozy Corner Cottage- 2 blocks to Lake Michigan. Walk to Deland Park and Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Cozy Corner Cottage by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, ...
From $186 per night (USD)
VRBO
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 $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
Click For Pricing
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 ...
Click For Pricing
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 $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)
VRBO
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)
VRBO
From $130 per night (USD)
Expedia
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)
Expedia
From $1267 per night (USD)
VRBO
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)
VRBO
From $151 per night (USD)
Expedia
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)
Expedia
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)
Expedia
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)
Expedia
From $163 per night (USD)
VRBO
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)
VRBO
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
Click For Pricing
Expedia
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, ...
Click For Pricing
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

Search Your Destination Now!

Sheboygan Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 109 Rentals