Kid-friendly vacation rentals in Sheboygan

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Sheboygan

Guests agree: these kid-friendly rentals are highly rated for location, cleanliness, and more.

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Guest favourite

Cottage in Oostburg

4.97 out of 5 average rating, 234 reviews

Sandalwood Cottage - 300 Feet From Lake Michigan

A HIDEAWAY one mile East of I-43 nestled in beautiful wooded acreage across from Lake Michigan, on a private drive. Just South of Sheboygan. Close by: Whistling Straits & PGA golf courses. Ice Age Trail in the Kettle Moraine, Elkhart Lake - Road America, Charter Fishing, Kohler Andrae State Park, Several State & local beaches, & several 5 star restaurants. 2 hours & 20 min from Chicago. 45 min from Milwaukee, 65 min from Green Bay. Rest, Relax and Unwind in the tranquil setting at Sandalwood.

Jan. 2 – 9

$238 CAD per night

Guest favourite

Home in Howards Grove

4.95 out of 5 average rating, 152 reviews

Spacious lower level priv entrance no cleaning fee

Entire basement is for rent with a separate entrance. Kitchen area includes refrigerator, microwave, coffee pot, toaster, sink, dining table and chairs. NO STOVE OR OVEN IS AVAILABLE. Free Wifi and Cable TV. Air conditioning. Plenty of parking, keyless entry. 14 min to Road America, 13 min to Kohler, 9 min to Whistling Straits, 5 min to Lakeland University, 1 hr to Milwaukee, 1 hr to Green Bay. Lots of nice amenities, clean, spacious. No cleaning fee. Unit NOT set up for babies or toddlers.

May 4 – 11

$158 CAD per night

Guest favourite

Home in Sheboygan

4.96 out of 5 average rating, 154 reviews

Dog Friendly Blue Door Cottage / Fully Fenced Yard

Nobody should have to leave their fur baby behind while on vacation. This is exactly why we created this comfortable home with your family & puppy in mind. You'll be at ease knowing that your pooch will be having just as much fun as you are. Modern hints are complemented by the cozy, welcoming decor found throughout. The coffee bar is a fav for any morning person, and the "take-a-wine leave-a-wine" wine bar offers evening excitement! The huge yard features a fire pit, gas grill, & cornhole.

Jan. 9 – 16

$228 CAD per night

Guest favourite

Home in Sheboygan

4.99 out of 5 average rating, 190 reviews

Woodland Creek Retreat: explore & relax!

Lovely home nestled in 9 acres of peaceful woodland. 1.5 miles off I-43. Enjoy a walk in the woods or enjoy the dunes and wonderful views of Lake Michigan from Terry Andrae State Park only .2 miles away! Enjoy relaxing on the front porch or taking in the view of the woods from the spacious back deck. Be on the lookout for turkeys and deer. Wonderful wood burning fireplace and extensive game collection(500+) for staying in! We love the cozy and open cabin feel and hope you will too!

Oct. 18 – 25

$443 CAD per night

Guest favourite

Home in Sheboygan

4.97 out of 5 average rating, 151 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.

Jul. 3 – 10

$243 CAD per night

Guest favourite

Apartment in Sheboygan

4.92 out of 5 average rating, 399 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.

Oct. 24 – 31

$139 CAD per night

Guest favourite

Apartment in Kohler

5.0 out of 5 average rating, 158 reviews

Church Street Romance & Retreats-Village of Kohler

“A well-appointed, cozy and stylish retreat close to everything in Kohler.” -Kim Take the stairs to my secluded 2nd floor tree view retreat! A private side entrance and open floor plan flanked by two bedrooms makes this unit perfect for couples or a girl's getaway spa weekend. Romantic turn-of-the-century touches meet modern convenience & comfort. Baker furniture, previously a Kohler Company, can be found throughout the apartment enhancing your Village of Kohler stay.

Nov. 1 – 8

$273 CAD per night

Guest favourite

Home in Sheboygan

4.94 out of 5 average rating, 172 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.

Oct. 3 – 10

$508 CAD per night

Guest favourite

Apartment in Sheboygan

4.84 out of 5 average rating, 186 reviews

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

Oct. 11 – 18

$99 CAD per night

Superhost

Guesthouse in Sheboygan

4.83 out of 5 average rating, 369 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!

Mar. 14 – 21

$199 CAD per night

Guest favourite

Apartment in Waldo

4.98 out of 5 average rating, 259 reviews

The Blue Cobb House

My place is close to 20 minutes south of Elkhart Lake and Road America. You’ll love my place because of the outdoors space, the comfy bed, and the kitchen. My place is good for couples, solo adventurers, and business travelers. The Blue Cobb House is about 15 minutes from Kohler-Andrae State Park and 30 minutes from Harrington Beach State Park. The Kettle Moraine area is just to our west and it is filled with hiking trails.

Mar. 30 – Apr. 6

$155 CAD per night

Guest favourite

Apartment in Sheboygan

4.89 out of 5 average rating, 271 reviews

Spiritual Vibes Downtown Walk-up

New art and hand crafted decor. Some are even available for purchase, others are for guests to enjoy during their stay. Cozy, inviting, private apartment close to restaurants, shops and entertainment. Wonderful morning and evening light. Large deck for relaxing outdoors or enjoying the sun. We have a storage shed for bikes, strollers and the like if needed. Just give us the heads up and we'll give you the key.

Dec. 27 – Jan. 3

$145 CAD per night