Family-friendly holiday rentals in Sheboygan

Modern Upstairs Apt - Steps from Lake Michigan

Have you ever wondered what Lake Life is like? Here is your chance! This is 1 of 2 AirBnB units in this cute duplex Come stay in this beautiful upper apartment located just one block from Lake Michigan. Take a quick walk to the lake in the morning to jump on your fishing boat or take the family to the beach in the afternoon! Located close to shopping and many local bars and restaurants within walking distance. You'll find relaxation and a great time here at the heart of Sheboygan's Shoreline!

House Near the Lake

Get out and enjoy nature, then return to a quiet mix of modern and retro in this family home only a block away from Lake Michigan. There are three parks and two beaches within a mile, as well as Terry Andrae State Park about 10 minutes away. If the outdoors aren't your thing, downtown Sheboygan hosts the Kohler Art Center, The Weil Center, Blue Harbor, and the Children's Museum, with Road America only 30 minutes away. Located between Milwaukee and Green Bay, this home has all the conveniences.

The Beach | Sheboygan 2Br/1 Ba

Welcome to the Beach, a lakeside retreat in the heart of Sheboygan. Located just 3 blocks from Lake Michigan and a stones throw to down town Sheboygan, The Beach is the perfect place to center your visit to Eastern Wisconsin. The Beach is the main floor unit of a duplex featuring 2 bedrooms, 1 bathroom, a well stocked kitchen, a cozy living room, fast wifi and convenient amenities. We have an easy check out with no to-do lists. Just pack and go! *New cleaning staff hired January 2023!*

Dog Friendly Cozy Cottage Rental on Lake Michigan!

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LUX Downtown Escape | Outdoor Movie Screen

Welcome to our beautiful 2-bedroom historic home in Downtown Sheboygan! This charming and well-appointed residence offers a comfortable and stylish stay for your visit to the area. From the Chef’s kitchen, comfortable living room, and peaceful backyard, to its prime location within walking distance of Sheboygan's vibrant nightlife, theater, and restaurants, you'll have everything you need right at your doorstep. The home is also just a few blocks from Lake Michigan's beautiful beaches.

Spacious/stylish, 2br loft

Lots of space in active downtown Sheboygan. Full kitchen w/essentials, washer/dryer, 1.5 baths, 2 queen, 2 twin ready for family/friends. Stocked w/home essentials. 3 Smart TVs, free WIFI. Pay-as-you-go parking lot in rear but free nights/weekends. Wonderful walkable neighborhood near shops, restaurants, art & children’s museum, river walk & lake front (a bit further). Short drive to Kohler, Whistling Straits golf course, Shops at Woodlake & Kohler Design Center. Marcus cinema near by.

Lovely modern two bedroom home with fire pit

Newly renovated two bedroom home just a mile from the beach and five star restaurants. Enjoy a game of golf at world class Whistling Straight. Car enthusiasts will love Elkhart Lake Road America. Salmon fishing the Great Lake Michigan or just have a relaxing time around the fire pit. There is a laundry with washer/dryer, steamer and folding table. Dogs under 30 pounds. No cats sorry. No smoking in the house. Ample street parking at the front door. Fire pit in back yard.

Cozy Sheboygan Upper

We began caring for this home and property in 2018, and this 1870's home needed some love. We have been steadily remodeling since we moved in and it's starting to feel pretty great. We're excited to share it and the neighborhood with you. We are two blocks west of North Beach/Deland Park, 4 blocks to the river front boardwalk, home to many restaurants, cafe's, and shops. We are also four quick blocks to downtown which hosts many more restaurants, shops, museums and parks.

King Bed Near Lake w/ Fire Pit & Pack N Play

Welcome to the Getaway! Getaway: noun - an act or instance of getting away; a place suitable for a vacation You will unwind in this peaceful 3 bedroom lower unit near Lake Michigan, Whistling Straits and Kohler/Andrae State Park. You can enjoy an evening around the fire pit, or if you don’t feel like staying in, head out to discover some of Sheboygan’s many hidden gems. If this unit is booked for your dates, send me a message to ask about our other available listings.

Sheboygan Surf House - Jetties

Located just 24 steps above Wisconsin's first Surf Shop, EOS Surf. Our Urban living oasis is a fully equipped studio apartment conveniently located in the heart of downtown, just steps from bars and restaurants and only blocks to Lake Michigan South Pier and Blue Harbor. Whether you are here for adventure sports like Surfing on the Great Lake, Kite boarding, charter fishing, a Wedding or leisure time SSH is perfect for you. Support Dog friendly

One Bdrm Apt - The Erie House near lake & downtown

This house was built in 1888 as a single family home and retains its nineteenth century charm along with today's modern conveniences. The location is just walking distance from both majestic Lake Michigan to the east and Sheboygan's charming downtown to the west. The lodging, which sits in an attractive, tree lined neighborhood, has been divided into several living units in which you will be staying on the first floor facing Erie Avenue.

Carriage House Sheboygan, Lake Mich beach access!

The Carriage House is the perfect getaway. Located in a beautiful historic neighborhood with Lake Michigan public beach access across the street, 100 yards away. Ideal for a family of four or an individual in town for business. Amenities have been thoughtfully placed to create the most comfortable and convenient stay for guests. We pride ourselves on ensuring you enjoy your stay with us and guarantee you'll love the neighborhood!