Family-friendly vacation rentals in Sheboygan

Apartment in Ellis Historic

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, 212 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, 124 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.

A sunlit corner nook displays a wooden bench adorned with plush, colorful pillows in varying textures. A small circular table holds a potted plant, while a larger leafy plant is positioned nearby. Sheer curtains allow soft light to filter into the space.

4.92 out of 5 average rating, 102 reviews

Coastal Comfort Near Lake MI & Downtown

Welcome to the Coastal Comfort! Comfort: noun - a state of physical ease and freedom from pain or constraint Come in and unwind at our coastal 3 bedroom lower unit home near Downtown Sheboygan, Lake Michigan, Whistling Straits and Kohler/Andrae State Park. You can enjoy an evening at home with all your favorite streaming services, or 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.

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, 238 reviews

Boutique Wellness Retreat - Hot Tub and Fireplace

Enjoy the Holidays at 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!

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, 151 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 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, 147 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.

Loft in Downtown Sheboygan

A spacious living area features a dark leather sectional sofa with colorful throw pillows. A textured ottoman sits in front, while natural light streams through large windows, illuminating the warm brick wall and wooden furniture. A decorative coffee table holds books and a candle.

4.97 out of 5 average rating, 115 reviews

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.

4.98 out of 5 average rating, 184 reviews

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.

Apartment in Sheboygan

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.

Apartment in Ellis Historic

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, 543 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, 209 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.

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, 501 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!

4.96 out of 5 average rating, 138 reviews

A bright seating area features two modern armchairs and a cozy rug. Large glass doors frame views of the beach, allowing natural light to fill the space. A tall bookshelf holds books and decorative items, while a TV is positioned for entertainment.

Condo in Sheboygan

Beachside Condo w/ Stunning Lake Views

🌅 Upper-Level Lake Views from Dual Decks 🏖️ Just 200 Feet to the Beach 🌇 Walkable to Shops, Dining & Riverwalk 🛏️ King + Queen Bedrooms | Sleeps 4 🔥 Electric Fireplace, Roku TV & Cozy Lounge Vibe ☕ Coffee Bar, Full Kitchen & Lake Breezes 🪂 Steps from Kite Park, Surfing & Waterfront Trails 🧺 In-Unit Washer/Dryer + Beach Gear Included

Popular amenities for Sheboygan family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

5 out of 5 average rating, 201 reviews

Cabin in Cascade

hot tub and sauna on 5 private acres

The exterior of the chalet displays a striking blue facade, enhanced by numerous tall trees surrounding the property. A spacious driveway leads to the two-car garage, while a small front porch awaits at the main entrance.

5 out of 5 average rating, 32 reviews

Sheboygan Chalet | Nature, Arcade, Sauna & Hot Tub

5 out of 5 average rating, 12 reviews

A spacious country home features a mix of stone and siding on the exterior. The front porch, accented with chairs, opens to a well-maintained lawn. A large driveway leads up to the entrance, framed by lush greenery and trees.

Home in Waldo

Spacious Home - 4 BR/2.5 Bath + Hot Tub + Game Rm

4.98 out of 5 average rating, 97 reviews

Home in Elkhart Lake

Fernwood Elkhart Lakefront Retreat w/ Pier, kayaks

4.94 out of 5 average rating, 64 reviews

A two-story home is seen with gray siding and brown shutters, featuring a covered front porch supported by wooden columns. Lush green shrubs and flower beds line the walkway, while a well-maintained lawn extends around the property. A car is parked in the driveway.

Home in Random Lake

Oma's Beach House

5 out of 5 average rating, 5 reviews

Hot Tub, Kayaks, SUP's & Firepit

4.94 out of 5 average rating, 135 reviews

An outdoor fire pit is surrounded by four wooden Adirondack chairs, set against a backdrop of snow-covered rocks and bare trees. The cabin, with its rustic wooden structure and metal roof, is visible in the background under a clear blue sky.

Cabin in Oostburg

HOT TUB w/ Beach Access near Kohler-Andrae

The exterior of a contemporary home is depicted, featuring a combination of wood and stone finishes. Lush greenery and flowering plants frame the entrance, while trees line the background, creating a serene natural setting.

5 out of 5 average rating, 39 reviews

The Woods Estate walk to RoadAmerica modern luxury

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 287 reviews

A quaint living space features an antique-style fireplace made of dark wood, with a circular mirror above it. A flat-screen television is mounted on the wall opposite a small table and a suitcase rests on the hardwood floor, accompanied by a decorative flower arrangement.

Apartment in Waldo

The Blue Cobb House

A charming white house is seen nestled among lush green trees and colorful foliage. A well-manicured lawn leads up to the front porch, which features a dark roof and an inviting entryway. A white picket fence outlines the property, enhancing its quaint appeal.

5 out of 5 average rating, 20 reviews

Riverside House

4.97 out of 5 average rating, 109 reviews

The cabin stands amidst lush greenery with a gently sloping lawn leading to a stone pathway. The modern exterior features large windows and a spacious upper deck surrounded by trees, providing a serene lakeside retreat.

Chalet in Campbellsport

Long Lake Chalet

4.99 out of 5 average rating, 86 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

The dining area features a wooden table set with dark bowls and glassware, illuminated by a soft, modern light fixture. Natural light filters in through two large windows, casting a warm glow on the space. A decorative runner is placed center on the table.

5 out of 5 average rating, 26 reviews

Stylish brick cottage - family & pet friendly

4.96 out of 5 average rating, 47 reviews

The exterior of the home features a charming two-story design with a gabled roof and a welcoming front entrance. Large windows allow natural light to fill the space. A small seating area is visible on the front patio, complemented by greenery and a neatly landscaped yard.

Home in Ellis Historic

The perfect location!

5 out of 5 average rating, 71 reviews

A spacious living area features a comfortable navy blue sectional sofa, complemented by two cushioned chairs. A wooden coffee table sits at the center, while artwork adorns the walls. Soft lighting from multiple chandeliers creates a welcoming environment.

Home in North Point

Sheboygan's Great Lake's House

Apartment in Ellis Historic

A renovated historic home displays a charming exterior with wide steps leading to a wooden front door. Flanking the entrance, tall evergreen trees create a natural boundary. The building features multiple large windows, enhancing its traditional architectural style.

4.96 out of 5 average rating, 89 reviews

Quaint Blast from the Past - walk to lake/8th st

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

A spacious room features two large beds adorned with patterned bedding. Natural light filters through sliding glass doors leading to a balcony. A ceiling fan enhances airflow, while a large mirror and dresser provide functional space. A blue area rug adds a cozy touch to the hardwood floor.

Hotel room in Elkhart Lake

4.33 out of 5 average rating, 6 reviews

Stay in the heart of Elkhart Lake at Victorian Inn Resort

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.

4.98 out of 5 average rating, 43 reviews

Holiday Home for 8ppl w/ Hot Tub in Plymouth, WI

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, 9 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.