Family-friendly vacation rentals in Sheboygan

A well-lit bedroom features a spacious bed with a dark headboard and light bedding. Two bedside lamps illuminate the room, complemented by natural light from the two windows. A wall-mounted television adds functionality, while a piece of art decorates one wall, enhancing the inviting ambiance.

4.98 out of 5 average rating, 205 reviews

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!

A cozy living area is filled with neutral-toned furniture, including a large sofa, accent chairs, and a circular coffee table. Natural light filters in through large windows, highlighting the wooden floors and a decorative area rug beneath. Soft green accents are present in the lamps and curtains.

4.98 out of 5 average rating, 120 reviews

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.

4.97 out of 5 average rating, 142 reviews

A wooden table displays a variety of items: an open book, a lime, a glass filled with dark liquid, and a bottle of rum beside a vintage Coca-Cola. A bouquet of vibrant flowers sits neatly in the background, with light filtering through a window.

Apartment in Kohler

The Hemingway on Church - It Tolls For Thee

"Kristine's property has all the charm of a modern day Mayberry" -Michael This 1906 historic home is nestled in the heart of the equally historic "Village of Kohler." Completely remodeled in 2019 adding Kohler spa amenities and modern touches to its original charm. Mixing modern & antique furniture finds like the Hemingway Sideboard (which inspired the literary theme) make this historic hideaway a true Kohler destination. "You cannot get a better location in Kohler than this house!" -Dennis

Apartment in Downtown Sheboygan

A leather sectional sofa is positioned beside a round coffee table, set on a textured area rug. A vintage surfboard is displayed above the couch, complementing the decor. A chair and lamp provide additional seating, while a small dresser holds a decorative lamp, enhancing the cozy ambiance.

4.91 out of 5 average rating, 149 reviews

Sheboygan Surf House - North Point

This super spacious studio apartment is the largest of our 3 spaces, located above Wisconsin's first Surf shop which is located in the heart of Sheboygan's Downtown District. Located directly next to bars , shopping and widely known restaurants like Tratoria Stephanos, Feild to Fork and IL Ritrovo, make walking everywhere easy. Whether you are here for beach days, a little get away or a wedding we are close to it all. Blue Harbor Resort, River front and the shores of Lake Michigan are close.

A cozy living room is featured, with a dark sofa, light-colored chairs, and a round pouf. A woven pendant light hangs above, illuminating textured wall art. Natural light filters through multiple windows, highlighting a striped area rug laid on the wooden floor.

4.9 out of 5 average rating, 109 reviews

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!*

A cozy backyard oasis is illuminated in evening light, featuring comfortable seating around a fire pit. An outdoor movie screen projects a vibrant image onto the adjacent wall, surrounded by lush landscaping and wooden fencing that enhances privacy.

4.95 out of 5 average rating, 139 reviews

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.

A well-lit living area features a neutral-colored sofa adorned with a soft throw. A glass coffee table sits on a patterned rug, complemented by a wicker basket. Natural light filters through the window, illuminating the space and the nearby armchair.

4.98 out of 5 average rating, 181 reviews

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.

A hot tub, illuminated with soft blue lights, features cascading water and inviting seating. Adjacent, a traditional sauna with wood paneling provides a relaxing retreat. Decorative cushions accent modern chairs nearby, enhancing the tranquil space.

4.98 out of 5 average rating, 228 reviews

Boutique Wellness Retreat - Hot Tub and Fireplace

Enjoy this beautiful boutique home. New patio and deck! Hot tub/Dry Sauna! Comfort and charm throughout. Cooks kitchen with all amenities. Primary bedroom with King size bed. Secondary bedroom has 2 twin beds. The beautiful fireplace in the living room is perfect for a relaxing couples evening. Enjoy a glass of wine or local brew on the patio while you grill out. EV Charger and E-Bikes to explore the area. Sonos audio throughout. This beautiful boutique home is sure to impress!

A comfortable living area features a sectional sofa in a soft grey hue, a rustic wooden coffee table, and natural light streaming through large windows. Unique décor includes a vintage style chair and a wall-mounted shelf with plants and books.

4.93 out of 5 average rating, 534 reviews

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.

A tranquil view of Lake Michigan at sunset, where calm waters reflect soft hues of orange and pink. The sky showcases wispy clouds, and a distant bird is seen soaring above the serene landscape, creating a peaceful setting.

4.94 out of 5 average rating, 208 reviews

Beachfront getaway in Sheboygan

One of the few homes in Sheboygan that walks out onto the sands of Lake Michigan, this 3 bedroom/ 2 bath home is meant for total relaxation and fun. The open kitchen, dining and living room is full of light from the sliding glass doors on the back of the house, which access a deck and a large back yard. Upstairs is a spacious loft with a pull out couch. Fire pit in the back yard. Just steps from a playground at King Park. Amazing sunrises, worth waking up for.

A spacious living room is equipped with a comfortable sofa and two armchairs. A TV screen is positioned adjacent to an original fireplace, which now houses an electric device. Natural light enters through a window, and a decorative area rug enhances the room's charm.

4.87 out of 5 average rating, 112 reviews

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.

Guesthouse in North Point

A view of the serene shoreline along Lake Michigan is presented, framed by lush greenery. A blue railing leads down toward the beach, where sand and water are visible, inviting outdoor activities. The sky is overcast, creating a calm atmosphere.

4.82 out of 5 average rating, 497 reviews

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!

Popular amenities for Sheboygan family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a pool

Apartment in Elkhart Lake

A spacious room features two queen beds dressed in light-colored bedding. A wooden dresser and a desk are positioned against the wall, with natural light entering through sliding glass doors leading to a balcony. A ceiling fan adds comfort to the ambiance.

4.62 out of 5 average rating, 21 reviews

Siebkens Lockout Unit

Home in Kiel

4.94 out of 5 average rating, 17 reviews

Family Home w/ Indoor Pool ~ 2 Mi to Elkhart Lake!

4.98 out of 5 average rating, 43 reviews

The exterior of a two-story home is portrayed, featuring a welcoming front porch with potted plants. Lush green grass lines the pathway leading to the stairs. The facade combines traditional elements with modern updates, reflecting a craftsman style. A clear sky with scattered clouds adds to the scene.

Home in Plymouth

Private Home 4 BR+2Ba, Heated Pool by Road America

Apartment in Elkhart Lake

A living room featuring large windows that provide views of the surrounding landscape. A patterned armchair invites relaxation alongside a small side table. A white fireplace serves as a focal point, with a stylish arrangement of decorative items above it. A soft area rug covers the hardwood floor.

5 out of 5 average rating, 11 reviews

Resort Condo on Elkhart Lake

Hotel room in Elkhart Lake

A well-lit room features two spacious beds dressed in crisp white linens. A flat-screen television is mounted on the wall, while a dresser provides storage. A small desk is set against one wall, accompanied by a decorative indoor plant in a pot.

5 out of 5 average rating, 8 reviews

Resort Life 2 Queen Suite

A spacious room features a king-size bed with a textured blanket. Modern appliances, including a refrigerator, are visible. A television is mounted above a decorative fireplace, and a small desk with a chair is positioned nearby. Natural light is welcomed through a door leading to the outside.

Hotel room in Elkhart Lake

Sleeps 8! 2 Full Bath with Kitchenette!

4.27 out of 5 average rating, 15 reviews

A cozy bedroom features a spacious bed with a light-tone blanket, complemented by two wooden nightstands. A large window with a sliding door offers access to a balcony. Dark curtains frame the window, and a flat-screen television rests on a wooden dresser.

Condo in Elkhart Lake

Siebkens 1 bedroom condo

An indoor pool is framed by natural stone and wood paneling, with large windows allowing natural light. Lounge chairs are arranged at one end of the pool, offering a relaxed setting. The pool area is spacious, creating a calming atmosphere for leisure activities.

Home in Plymouth

5 out of 5 average rating, 3 reviews

Road America lake house.

Family-friendly home rentals with air conditioning

A contemporary living area features a brown leather couch paired with green and gray cushions. A circular mirror is set above a wooden coffee table adorned with a small potted plant. The space includes hanging greenery and a soft area rug, enhancing a calm ambiance.

4.94 out of 5 average rating, 53 reviews

Sleeps 7{SPACIOUS}Pets Welcome!

4.87 out of 5 average rating, 39 reviews

Geele Getaway 2 BD Comfortable Stay.

A comfortable living area features a plush sofa, a bean bag chair, and a modern television. A wooden dining table with three high stools is positioned in the center. Natural light flows in through large windows, enhancing the inviting space.

5 out of 5 average rating, 86 reviews

Recombobulation Station-Locally Owned Surf Escape

A serene beach stretches along the shoreline, with gentle waves lapping at the sandy coast. The sky is painted with soft pastel hues as the sun sets, casting a warm glow over the water. A few trees line the beach in the distance.

5 out of 5 average rating, 15 reviews

Clara Vida Inn- 1/2 Block from Lake and beach!

4.94 out of 5 average rating, 488 reviews

Home in Plymouth

Country Guest House - Beautiful Gardens!

An open living space features a round dining table with four chairs, complemented by a cozy seating area with a sofa adorned in warm tones. Natural light filters through large windows, while string lights add a gentle illumination to the ceiling.

4.92 out of 5 average rating, 36 reviews

Parkside Studio Apartment

A charming two-story house features a welcoming front porch with white railings. American flags adorn the porch, while potted plants add a touch of greenery. The exterior is clad in light siding, with large windows allowing natural light to enter the home.

4.93 out of 5 average rating, 82 reviews

Cozy 2BR Upper Apt • Quiet Area • 1 Mile to Beach

5 out of 5 average rating, 26 reviews

Clean, Comfy Stay Near Parks, Downtown & Lake!

Family-friendly home rentals with Wifi

The Victorian home showcases a charming, multi-level façade with intricate details and a light-colored exterior. Welcoming porches are present at the front, surrounded by well-maintained landscaping featuring green grass and vibrant flowers, all under a clear blue sky.

5 out of 5 average rating, 81 reviews

Updated Victorian in the Heart of Sheboygan

4.94 out of 5 average rating, 36 reviews

A functional kitchenette features wooden cabinets and a granite countertop. A black refrigerator and coffee maker are visible. The open layout includes a dining table and seating. In the background, a bathroom entrance and additional countertop space can be seen, enhancing the convenience of the space.

Guesthouse in Sheboygan

Unique Guest House close to everything

4.99 out of 5 average rating, 83 reviews

A spacious living area is highlighted by large windows allowing natural light to fill the room. Comfortable seating includes a sectional sofa and two armchairs, arranged around a stylish fireplace with intricate tile work. Light-colored curtains complement the modern decor.

Home in North Point

The Suncatcher -Steps from Lake - Fenced Yard

4.96 out of 5 average rating, 73 reviews

A comfortable living area is presented with two brown couches facing a coffee table. A television is positioned on a white entertainment unit against the wall. Natural light enters through double doors leading to the deck, enhancing the spaciousness of the room.

Guest suite in Waldo

Above Garage Apartment w/ Private Beach

4.96 out of 5 average rating, 46 reviews

The exterior view of the condo showcases a welcoming entrance with a private porch, adorned with white columns and railings. Lush landscaping enhances the property, and a subtle name sign identifies the villa, creating a charming and inviting atmosphere for guests.

Villa in South Pier

Lovely Lake Lookout - Cozy Condo Steps from Lake

The kitchen features a spacious granite countertop and a black sink, highlighted by wooden cabinetry. A large window allows natural light to fill the room, showcasing scenic outdoor views. Colorful yellow chairs and a small table create a cozy seating area nearby.

4.97 out of 5 average rating, 135 reviews

Lakefront Charmer, cheerful decor gorgeous garden

4.96 out of 5 average rating, 82 reviews

A well-equipped galley kitchen features modern appliances, including a dishwasher and stove. Light yellow walls enhance the inviting atmosphere, while wooden countertops offer ample workspace. Two high stools are positioned at the counter, and a door leads to the outdoor area, allowing natural light to fill the space.

Guesthouse in Sheboygan

Moonrise Kingdom surf shack. One block to beach.