Kid-friendly accommodation & holiday rentals in Sheboygan

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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.

1 – 8 Mar

$1,705 AUD total

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.

3 – 10 May

$1,219 AUD total

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.

9 – 16 Jan

$1,759 AUD total

Guest favourite

Home in Sheboygan

4.85 out of 5 average rating, 178 reviews

Serene Home One Block From Lake Michigan

Bring your loved ones to this spacious home a block from Lake Michigan and beautiful Deland Park! Located mere steps from North Beach and the local YMCA and minutes from downtown shops and nightlife. You will have the ability to be as relaxed or active as you wish while staying at our home. This is the perfect home for any group or occasion. Golfers will find this home located near some of the best courses in Wisconsin, 15 min from Whistling Straits! Within an hour of Milwaukee & Green Bay.

15 – 22 May

$2,384 AUD total

Guest favourite

Home in Plymouth

4.97 out of 5 average rating, 165 reviews

Wyatt's Country Home - King Bed!

Soak up the modern vintage charm of our fully remodeled and updated home! Thank you for choosing our sparkling clean space. Our home is nestled on two quiet acres just north of Plymouth in the peaceful country. Enjoy coffee as the sun rises from one of the two decks, or perhaps a cocktail by the fire as the sun sets. We ourselves lived in this home for our first 5 years and turned it into a beautiful and peaceful space for ourselves that we would now like to share with everyone.

14 – 21 Nov

$1,332 AUD total

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.

23 – 30 July

$1,822 AUD total

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.

26 Nov – 3 Dec

$994 AUD total

Guest favourite

Condo in Sheboygan

4.87 out of 5 average rating, 192 reviews

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.

24 Nov – 1 Dec

$1,908 AUD total

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.

3 – 10 Oct

$3,923 AUD total

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

4 – 11 Apr

$828 AUD total

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!

3 – 10 Nov

$1,541 AUD total

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.

29 Mar – 5 Apr

$1,200 AUD total