Family-friendly holiday 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.

4.99 out of 5 average rating, 275 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!

FamilyIndoor spacesOutdoor spaces

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.

4.96 out of 5 average rating, 145 reviews

Lakefront Charmer, cheerful decor gorgeous garden

This 2600 sqft lakefront home is a spacious retreat year round, friendly to kids and dogs. It is perched upon a bluff overlooking Lake Michigan with a gorgeous sunrise view. In winter, enjoy passing cargo ships and eagles along with ice formations. Inside, dine with seating and service for 12 after cooking in the spacious kitchen with wood fireplace. Kitchen, living room, dining room and 2 bedrooms have full lake view. 2 large screen tvs. Spa quality bath with whirlpool. Gas fireplace too!

KitchenIndoor spacesWalkability

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, 165 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.

KitchenIndoor spacesNearby

4.97 out of 5 average rating, 208 reviews

Couple's or Family fun- With outdoor Hot Tub!

Enjoy a Day or week for couples or families at this Beautifully updated beach house just one block from the Lake. Enjoy the backyard with pergola & 2-6 person Hot Tub ALL WINTER! Watch the sunrise & sunset from the second floor master balcony. Walk to the lake & beech just across the street. Close to downtown and parks. This three bedroom home will impress. Tastefully decorated seasonally. Large bathroom w/deep soaking tub. For treasure hunters, a Metal detector for family fun at the beach.

KitchenFamilyBiking

4.97 out of 5 average rating, 248 reviews

LUXE Manor With Modern, Elegant Vibes - 4,500 Sq

Modern chic blends with classic sophistication in this late 1800s Historic Manor, The Herman Hayssen House. Enjoy 4,500 sq ft of elegance and character that adorns this well-appointed home. Complete with 4 bedrooms, 3 full baths, and 1 half bath, many different areas for entertaining, both inside and out. The neighborhood is of the most elite in Sheboygan, situated between the lakefront and downtown and is a short drive to Whistling Straights and within an hour of Milwaukee and Green Bay.

KitchenIndoor spacesOutdoor spaces

4.96 out of 5 average rating, 183 reviews

An aerial view of a spacious home is surrounded by mature trees, showcasing a private sandy beach alongside Lake Michigan. The property features a pathway leading to the house, emphasizing its secluded setting amid natural greenery.

Home in Oostburg

Lake Michigan Beach Home by Frank Lloyd Wright pro

Beautiful view and sand beach on Lake Michigan, completely private, surrounded by mature white pine trees and cedar trees. The spacious home is fully equipped with an "eat in" kitchen, dining room, and living room entertainment space, den with a see-through log-fired fireplace, screened-in porch to accommodate additional eating space, large outdoor deck with grill and fire pit. A canoe and a row boat are available for the boating enthusiast, with life jackets and other floating devices.

FamilyIndoor spacesParking

4.95 out of 5 average rating, 133 reviews

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.

Loft in Sheboygan

Spacious/stylish, 2br loft

Beautiful, spacious loft in active downtown. Laundry, kitchen, 1.5 baths, 2 Qu, 2 Tw beds. Bakery & fitness studio on 1st floor (some a.m. noise). Stocked w/home essentials. Smart TVs, free WIFI. Pay-as-you-go parking in rear but free nights/weekends. Wonderful walkable neighborhood near shops, restaurants, art & children’s museum, river walk & lake front near-by. Short drive to Kohler, Whistling Straits golf course, Shops at Woodlake & Kohler Design Center. Marcus cinema near by.

Indoor spacesKitchenHospitality

The exterior of a charming house is depicted, showcasing a welcoming front porch with steps leading up. The porch features a small seating area and decorative plants, while lush green grass frames the path, adding to the inviting ambiance.

4.97 out of 5 average rating, 243 reviews

Logan's Guest Nest

Logan's Guest Nest is located in a nice small town feel area. With a small look on the outside your Nest has a big feel on the inside. Spacious rooms and quiet area to rest after a day at the many beaches lining Lake Michigan. Or coming back from the races at Road America. Not to mention a day of golf at the many area courses, Whistling Straits maybe. All these wonderful outings are just minutes from the Nest. Plenty of local dinning or delivery for a nice ending of the day.

KitchenIndoor spacesCleanliness

The image captures a scenic view from the deck, showcasing a lush green backyard leading to the shoreline of Lake Michigan. A fire pit is visible on the grass, and white planters frame the deck, while the sky displays a soft gray hue.

4.94 out of 5 average rating, 224 reviews

Stylish Getaway | Cozy Vibes | Perfect Girls Trip

Escape to a cozy, stylish retreat designed for relaxing weekends, girls trips, or family getaways. Start your morning with a sunrise and coffee on the patio looking out onto Lake Michigan, then spend the day exploring, and unwind at night around the firepit with a glass of wine. This home has everything you need for gathering and cooking together or cozying up to the fireplace and playing board games. A short walk to town, close to golf, breweries, winery, and a state park.

Indoor spacesFamilyTV

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, 594 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.

Indoor spacesFamilyCleanliness

4.88 out of 5 average rating, 217 reviews

A view from the open door showcases a spacious deck leading to a grassy area with trees. Beyond the greenery, the blue waters of Lake Michigan are visible, capturing a serene outdoor scene.

Apartment in Sheboygan

Beachside Lake View - 2br - First Floor - Garage

Located just one lot in from the beautiful shores or Lake Michigan. Amazing location provides year round stunning views . This is a lower 2 bedroom 1 bath condo in a 4unit building were all the units have the same basic layout. You can listen to the waves or walk just a few feet and have the sand on your feet. This condo features front and rear balconies. Makes for a great place to enjoy a weekend get away or a place to relax at night while on a business trip.

Indoor spacesFamilyCleanliness

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.

4.99 out of 5 average rating, 102 reviews

The Suncatcher -Steps from Lake - Fenced Yard

Welcome to the Suncatcher. Our cozy and bright Midwest retreat just a block away from Lake Michigan . Step into our lovingly remodeled 1930's home where modern comfort meets timeless charm. As you enter you will be greeted by the inviting warmth of exposed brick walls and abundance of natural light that fill every corner. With three bedrooms and two bathrooms, our spacious retreat is perfect for families, friends, or golf enthusiasts seeking a relaxing getaway.

KitchenIndoor spacesBathroom

Popular amenities for Sheboygan family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 301 reviews

A rustic modern home is showcased, featuring a spacious wraparound deck surrounded by lush greenery. An inviting hot tub glistens in the sun, and an arcade room with various games is displayed, offering entertainment options for guests.

Home in Elkhart Lake

The LODGE in Elkhart Lake. —-Hot Tub & Arcade—-

KitchenIndoor spacesParks

5.0 out of 5 average rating, 281 reviews

Cabin in Cascade

hot tub and sauna on 5 private acres

Indoor spacesKitchenNearby

4.97 out of 5 average rating, 111 reviews

Cabin in Elkhart Lake

Fernwood Elkhart Lakefront: hot tub, pier, kayaks

FamilyIndoor spacesBiking

4.97 out of 5 average rating, 34 reviews

Lakeview Farm | Beach · Hot Tub · Theater · Views

FamilyIndoor spacesHot tub

5.0 out of 5 average rating, 55 reviews

Cabin in Oostburg

Log Cabin At The Lake

FamilyKitchenAccuracy

4.98 out of 5 average rating, 54 reviews

Villa in Plymouth

Road America Oasis: 25 Acres, Hot Tub & Orchard

KitchenFamilyOutdoor spaces

4.98 out of 5 average rating, 88 reviews

Home in Cleveland

Hidden Haven - Modern Cottage w/ Hot Tub & Views

KitchenFamilyLocation

5.0 out of 5 average rating, 20 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 Riverfront home - 4 BR/2.5 Bath + Hot Tub

KitchenIndoor spacesLocation

Family- and pet-friendly home rentals

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, 218 reviews

Lovely modern two bedroom home with fire pit

KitchenFamilyHiking

Superhost

The kitchen area offers light wood cabinetry and a breakfast bar, with a dining table that seats four. Large sliding glass doors provide views of the lake, while ample counter space accompanies a full-size refrigerator and modern appliances.

4.83 out of 5 average rating, 228 reviews

Dog Friendly Cozy Cottage Rental on Lake Michigan!

Indoor spacesFamilyValue

A cozy living room is presented with floral wallpaper and natural light from a large window. Soft couches adorned with decorative pillows are complemented by armchairs. A dark wood coffee table occupies the center, while a floor lamp and side table add functionality and warmth.

4.85 out of 5 average rating, 110 reviews

The Garden | Sheboygan 2 Br/1Ba, Pet Friendly

KitchenFamilyQuiet

A dining area is furnished with a wooden table surrounded by a mix of white and woven chairs. A decorative vase with greenery sits at the center of the table, complemented by a warm-toned armchair nearby. A colorful area rug adds an inviting touch to the hardwood floor.

4.9 out of 5 average rating, 184 reviews

Spacious Home Near Lake MI w/ Fire Pit

FamilyIndoor spacesOutdoor spaces

4.86 out of 5 average rating, 118 reviews

The exterior of a spacious lakeside home is showcased, featuring large windows and a welcoming porch. A green lawn extends towards the water, accompanied by bright blue kayaks and a swing set. A tall tree provides shade, enhancing the outdoor ambiance.

Cottage in Random Lake

Private 3 bedroom lake house

KitchenFamilyNearby

4.98 out of 5 average rating, 323 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.

Flat in Waldo

The Blue Cobb House

FamilyKitchenRiver

4.94 out of 5 average rating, 521 reviews

Home in Plymouth

Country Guest House - Beautiful Gardens!

KitchenFamilyAir conditioning

4.96 out of 5 average rating, 163 reviews

A modern single-story home features a light gray exterior with a striking yellow front door. Large windows provide abundant natural light, while a well-maintained lawn is complemented by colorful flower beds. Skylights on the roof enhance the home's contemporary design.

Home in Cleveland

Guest Favorite | Super Host + Clean & Modern Stay!

FamilyKitchenCleanliness

Family-friendly home rentals with a pool

Earthen home in Elkhart Lake

Secluded Elkhart Retreat | Pool, Hot Tub & Sunset

Indoor spacesKitchenPool

4.97 out of 5 average rating, 158 reviews

5.0 out of 5 average rating, 7 reviews

Home in Elkhart Lake

Lake Views | Walk Everywhere | 3BR Beach Resort

Indoor spacesFamilyLayout

Apartment in Elkhart Lake

An aerial view captures the expansive waters of Elkhart Lake, with shimmering reflections of sunlight. The shoreline is lined with lush greenery and a sandy beach, complemented by a few boats gently floating on the surface. Nearby, various residential structures can be seen nestled among the trees.

Lakefront Condo, Private Beach/Pool, Walk to Town

FamilyKitchenView

4.96 out of 5 average rating, 25 reviews

Superhost

Apartment in Elkhart Lake

Private Beach, Pools & Full-Kitchen

FamilyIndoor spacesCleanliness

5.0 out of 5 average rating, 11 reviews

4.97 out of 5 average rating, 60 reviews

An outdoor area features a heated swimming pool filled with clear blue water, surrounded by a spacious deck. A wooden pavilion with seating is positioned nearby, offering shade and a place to relax. Poolside lounge chairs are arranged for sunbathing.

Home in Plymouth

Road America Retreat-4 BDRM-2BA-Hot Tub+Pool

KitchenFamilyLocation

Superhost

Apartment in Elkhart Lake

VicVill | WaterViews | Vintage Charm Meets Comfort

KitchenFamilyLocation

New place to stay

5.0 out of 5 average rating, 17 reviews

Luxury Pool Retreat-2 Acres-Near Whistling Straits

FamilyKitchenGetting around

A sunlit balcony offers a serene view of the beach, featuring a round dining table and two intricately designed chairs. The railing showcases a classic white finish. Soft sand and a clear sky are visible in the distance, creating a peaceful outdoor setting.