Kid-friendly vacation rentals in Sheboygan

Find and book unique kid-friendly rentals on Airbnb

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Popular amenities for Sheboygan kid-friendly rentals

Kid-friendly house rentals

Superhost
Home in Sheboygan
4.76 out of 5 average rating, 21 reviews

Modern 5 Bedroom Getaway House

JanetRating, 5 stars7 months ago
Location was perfect for what we had on our plans. I would definitely recommend BookWorm Gardens. My grandchildren enjoyed the variety of games provided.
Top guest favorite
An entryway greets visitors with original hardwood flooring and contrasting dark wood accents. A set of green velvet chairs sits invitingly beside a sleek table, adorned with decorative items. Natural light enters through multiple windows, illuminating the space and highlighting the staircase.
Home in Sheboygan
4.99 out of 5 average rating, 132 reviews

2 Min Walk to Food, 15 to Pier! 4 Bedrooms 2K/2Q

RicciRating, 5 stars6 months ago
This is the second time I stayed at Chelsea’s house. It is the perfect location for the beach, the river and the downtown Sheboygan area and also super close to Kohler for the spa and food and wine festival! Perfect cozy home for a girls trip or a family get away!
Guest favorite
A cozy reading nook features a patterned armchair next to a side table, with a large window allowing natural light. White built-in shelves are filled with books and games. A blue tablecloth covers a table ready for gatherings, complemented by additional seating.
Home in New Holstein
4.86 out of 5 average rating, 139 reviews

Growe's Guest House - just like Grandma's!

Israel IzzyRating, 5 stars6 months ago
The place was clean, nice and good amenities. Mary was responsive to our questions and very helpful. We were there for the SCCA Championship races at Road America ! We Left at 7am and returned at 10pm everyday. We did enjoy it. We only wish the upstairs bathroom had a shower instead of a soaking tub. (Since 4 guys all trying to take a shower before rushing off to sleep. Very nice place.
Top guest favorite
Home in Glenbeulah
4.98 out of 5 average rating, 125 reviews

Stay at Sunrise LLC, Like being at Grandma's

DavidRating, 5 stars6 months ago
This place is suitable for a small family or a few adults. Very clean and well thought-out amenities made it quite attractive. Because we were very busy at Road America every day, we did not have an opportunity to use the kitchen except to make coffee, but had we wanted to cook, I'm sure we would have found everything needed. The only "warning" is that anyone with some mobility issues might find the stairway to the second floor a bit daunting. If we need a place in the area again, we would likely choose this house again.
Top guest favorite
Home in Sheboygan
4.98 out of 5 average rating, 65 reviews

The Suncatcher -Steps from Lake - Fenced Yard

EmilyRating, 5 stars2 weeks ago
I am quite picky when it comes to my stats at Airbnb. Jessica's place stands out. I'm not a fan of clutter and Sun Catcher was just perfect. Such a cozy bed and the layout is great. Would highly recommend.
Guest favorite
A dining area features a dark wooden table surrounded by six chairs, each with patterned cushions. A sideboard and display cabinet showcase decorative items. Natural light filters in through windows, highlighting the warm wood tones of the space.
Home in Sheboygan
4.85 out of 5 average rating, 27 reviews

*Centrally Located and Updated* The Barrel House

Kyle & CallieRating, 5 stars6 months ago
Two moms an infant and two adolescent children stayed for a quick weekend exploring Cheboygan and this place was perfect, Ryan our host was extremely responsive and helpful and everything was exactly as it was described. We are very happy with this stay.
Top guest favorite
An indoor recreational area is showcased, featuring a ping pong table and a foosball table. Comfortable seating is provided by a stylish chair and an additional lounge chair. The space is finished with a warm area rug and large windows that allow natural light to enter.
Home in Sheboygan
4.95 out of 5 average rating, 42 reviews

Wander Back Inn to Sheboygan

LaurieRating, 5 stars1 month ago
We had a great time at this place. Everything was as described. Very easy to work with and accommodating.
Guest favorite
A charming brick home is showcased with a welcoming blue front door. Two large windows flank the entrance, allowing natural light to illuminate the space. Lush greenery and flowering plants are present near the foundation, enhancing the home's inviting exterior.
Home in Sheboygan
4.95 out of 5 average rating, 221 reviews

Dog Friendly Blue Door Cottage / Fully Fenced Yard

ChristineRating, 5 stars1 week ago
I can’t gush enough about this place! I wish I would have stayed longer, and hope to return with my family later this summer. The yard is huge! Both local recommended restaurants I tried were fantastic. The shopping near by is plentiful, and the lake isn’t far away either although that’s not why I came. I just wanted to get out of Chicago for some peace and quiet. As a city girl, I ran into a little more wildlife than I was used to, but Jordan and his brother were super fast to respond, and quick to help me manage it! Throughout your stay, you can tell Jordan truly encourages traveling with your dog(s), and that kind of warm welcome is priceless.

Kid-friendly apartment rentals

Superhost
The living room features a cozy seating arrangement with two armchairs and a sofa, in front of a wooden coffee table. Natural light enters through two windows adorned with sheer curtains, illuminating the green walls and wooden flooring. A television is positioned on a media console against one wall.
Apartment in Plymouth
4.64 out of 5 average rating, 298 reviews

Pineyard Plymouth Apartment

CynthiaRating, 5 stars2 weeks ago
Kerry's flat was exactly as she described and exactly as pictured in the photos. The price point was also a plus -- artists who were firing a woodburning kiln just outside Plymouth. Climbing into those cozy sheets in such a cute place was soooooooooo much better than camping out as we had originally planned in. We have already booked another stay!
Top guest favorite
The living area features a spacious beige couch with an assortment of decorative pillows. A large area rug adds warmth to the hardwood floor. A flat-screen TV is mounted on the wall, and a desk with natural light invites productivity. Windows are dressed with sheer curtains.
Apartment in Port Washington
4.96 out of 5 average rating, 325 reviews

Grace Adventure House, walk to Port, Shops, Beach

BriannaRating, 5 stars1 week ago
I love the details David added to his home. I loved hanging out in it more than I wanted to go see sites because it was so comfortable and enjoyable. I forgot toothpaste and cotton swabs and he had it supplied. I loved sitting in the living room by the fire place heater and hanging with my family. I lived all his book nooks and unique furniture. David is very kind and accommodating. Loved the town of Port Washington with all of its charm and shops.
Top guest favorite
A cozy living room is presented, featuring a beige sofa adorned with red and white throw pillows. Two red chairs flank a wooden coffee table displaying decorative items. Natural light filters through sheer curtains, illuminating the plush area rug and enhancing the room's inviting atmosphere.
Apartment in Port Washington
4.95 out of 5 average rating, 276 reviews

Silvers Four-Six-Four *A home away from home*

SharonRating, 5 stars4 weeks ago
What a wonderful place for my sisters and I to meet up in Port Washington. It's cozy and clean with comfy beds. The kitchen was well stocked with all the pots, pans and coffee equipment we desired. It's walkable to cafes and restaurants and a cute little resale shop. We would definitely stay there again!
Top guest favorite
A comfortable leather sofa with patterned cushions is positioned in the living area. A wooden cabinet with glass doors displays decorative items. The room features a colorful area rug and walls that are partially adorned with wooden accents, contributing to a cozy ambiance.
Apartment in Port Washington
4.93 out of 5 average rating, 290 reviews

Homeport

BeverlyRating, 5 stars6 days ago
Amy's place was comfortable, peaceful and relaxing. Everything in the apartment worked great - there was nothing to need. Amy's place is within walking distance to many restaurants and shops in Port Washington and has a great view of the lake and marina. I highly recommend staying at Amy's Homeport.
Top guest favorite
An open living space is showcased, featuring a comfortable sectional sofa and a minimalist coffee table. A dining area with two stools is visible next to the kitchenette. Natural light filters through the windows, illuminating the neutral-toned furnishings and wood-style flooring.
Apartment in Sheboygan
4.97 out of 5 average rating, 157 reviews

Modern Upstairs Apt - Steps from Lake Michigan

SamRating, 5 stars4 days ago
Michelle's place has great access to the Bay area and greatly renovated. The primary bedroom with bath is gorgeous especially with heated tile floor. The second bedroom was a bit small but it was also comfortable. The second bath was behind the kitchen so the couple who used the second bedroom has to walk through the living room and the kitchen but it was not a big deal. We felt the coffee table in the living room was a bit small for four of us but again not a big deal at all. One thing we have noticed was the linen are high quality! And we paid the great price probably because it is early (water in Michigan lake was still pretty cold). Neighborhood restaurants were great and kitchen has all the tools and dishes for our first night dinner. We wished that we had access to outdoor grill but maybe it will be available during the summer. Great stay in small coastal town in WI. Highly recommended!
Top guest favorite
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
4.98 out of 5 average rating, 139 reviews

Lovely modern two bedroom home with fire pit

LeaRating, 5 stars4 days ago
We had an amazing stay!!! Ellen was extremely friendly, welcoming and made you feel right at home. The place was in spotless condition and it’s very apparent the owner takes top notch care of the unit! The unit was actually much larger and spacious compared to what I was expecting. Everything you need for a comfortable stay.. and more! You will not be disappointed with anything in this rental, that’s a guarantee!! Thank you, Ellen!
Top guest favorite
The exterior of a two-story home is shown, featuring a beige facade with white trim. A red door adds a pop of color, and flower boxes are mounted under the front windows. In the background, a clock tower is visible, indicating proximity to local attractions.
Apartment in Port Washington
4.97 out of 5 average rating, 183 reviews

Inn on Billy Goat Hill

JamesRating, 5 stars1 week ago
This stay was excellent for 3 nights while visiting our granddaughter at Concordia University. Especially appreciated were our personal welcome upon late arrival, very comfortable beds, super cleanliness, wonderful coffee choices, fruits, delicious cookies, fresh flowers, huge towels, shampoo & more! The stairs are steep so thankful we had a strong daughter and grandson to help carry our luggage up the stairs. We enjoyed being able to walk the quiet neighborhood and down to beautiful Lake Michigan. Thank you for sharing your lovely home with us!
Top guest favorite
A cozy living area is highlighted by a large window that overlooks greenery. A comfortable dark sofa and wooden coffee table are arranged around a patterned rug. A rocking chair and armchair provide additional seating, while potted plants add a touch of nature.
Apartment in Sheboygan
4.93 out of 5 average rating, 483 reviews

Cozy Sheboygan Upper

Heather Rating, 5 stars2 weeks ago
This was the type of stay where you wish you were able to hang out with the owner because the place had such a great vide. It was such a comfortable place- loved the plants, furniture, art!! The neighborhood was right near the lake. Near a great many restaurants, coffee places- several recommendations from their suggestions. We went to several store that knew Craig and had great things to say. I highly recommend this very lovely home!!

Kid-friendly condo rentals

Top guest favorite
The exterior of a renovated two-story townhouse is displayed, featuring a contemporary design with dark grey siding and bright red front doors. Lush landscaping with various shrubs and flowers frames the walkway leading to the entrance. A paved driveway extends along the side of the house.
Condo in Sheboygan
4.97 out of 5 average rating, 65 reviews

Urban Townhouse

HalieRating, 5 stars1 month ago
this was the perfect place for our stay. we wanted a condo with a hot tub so we could relax and hang out. our plan was to spend a good amount of time hanging out and chilling at the BNB, and just go to a couple different places around Sheboygan. this condo was perfect for that. I have no complaints, this place was perfect. if I ever return to Sheboygan, we'll definitely be looking to stay here again.
Top guest favorite
The exterior of a charming two-story building is shown, featuring white siding and red roofs. Stone pillars flank the entrance, and a spacious porch is visible on the lower level. Well-manicured grass and landscaped areas surround the structure.
Condo in Sheboygan
4.98 out of 5 average rating, 41 reviews

A Glorious Getaway Sheboygan - LUX Lake Condo

JohnRating, 5 stars1 month ago
Susan was exceptionally responsive and inviting. She let us arrive early for our Mother's celebration of life weekend. It was easy to find once you figured out the address and unit numbers. Parking was ideal and plentiful. You can see the beach and lake from the walk out balcony.
An open-concept living area features a cozy gray sofa and a round dining table with light-colored chairs. A modern electric fireplace is positioned beneath a large wall-mounted TV. Natural light floods in through expansive sliding glass doors, leading to a furnished balcony.
Condo in Sheboygan
4.79 out of 5 average rating, 14 reviews

Modern South Pier Condo on Sheboygan River!

LauraRating, 5 stars4 months ago
Nice, comfortable condo. Easy parking, elevator, cozy.
Guest favorite
A spacious living area is highlighted by large glass sliding doors that offer views of a green landscape. A comfortable sectional sofa is adorned with colorful cushions, complemented by a round coffee table on a patterned rug. A vibrant piece of wall art adds a touch of charm.
Condo in Sheboygan
4.97 out of 5 average rating, 31 reviews

Heavenly Condo in the Malibu of the Midwest

LisaRating, 5 stars2 months ago
Debbie was super responsive from day 1 onward. Really enjoyed working with her for our 6-day stay. The place was nice and warm despite the sub-zero temps we had when there. Bed was comfortable and lots of hot water for showers. New appliances so meals in were easy. All in all a great place to stay. Thank you Debbie.
Top guest favorite
A well-lit bedroom features a queen-size bed with a patterned blue and white duvet, complemented by neatly arranged towels. A nightstand with a bedside lamp stands beside the bed, and natural light enters through a window dressed with blue curtains.
Condo in Sheboygan
4.93 out of 5 average rating, 40 reviews

Ellis District Urban Lake Condo

ChristyRating, 5 stars1 week ago
Sara was very responsive accommodating for our needs. The space itself was spacious for the size, the kitchen was well equipped with any cooking you may do, tons of towels and travel size toiletries in vase you forgot something walking distance to the marina was a nice option, however it was a tad nippy so I chose to stay inside while my husband and son were in the airspft event. will definitely stay again!
Top guest favorite
A serene view from the second-story balcony overlooks the sandy beach and expansive lake. Soft waves lap at the shore under a cloudy sky, with a faint rainbow visible in the distance, creating a tranquil atmosphere for relaxation.
Condo in Sheboygan
4.97 out of 5 average rating, 36 reviews

Beach condo for 12: 4 bdrms, 2+ baths, treadmill

KateRating, 5 stars1 week ago
We booked this condo for a girls' weekend / reading retreat. The condo was huge, the kitchen was well stocked, and there was plenty of space to spread out. Sheboygan is an adorable town, and the view of the beach was gorgeous even if the weather wasn't quite warm enough to get out there and enjoy it.
Guest favorite
A bridge is seen raised, allowing a sailboat to pass through the waterway. Clear blue skies provide a backdrop to the scene, while trees with autumn foliage line the riverbank. The calm water reflects the colors of the surroundings.
Condo in Sheboygan
4.93 out of 5 average rating, 86 reviews

Janelle's Dockside Condo

ElaineRating, 5 stars2 weeks ago
We loved everything about this stay. Janelle has created a very beautiful space with absolutely everything we needed for a peaceful vacation. It is spacious and immaculately clean. The location is priceless. We had an easy walk to Lake Michigan, great restaurants, fun shops, and great coffee. We will definitely be back!
Top guest favorite
An open concept kitchen and living area features a large island with seating for four, complemented by modern bar stools. Dark cabinetry contrasts against a brick wall, and stainless-steel appliances are visible, enhancing the functional design of the space.
Condo in Elkhart Lake
5 out of 5 average rating, 28 reviews

Car Condo Rental in Elkhart Lake

AaronRating, 5 stars6 months ago
We loved how it was decorated and it had everything we needed even a wine bottle opener! Also it is right down the road from Road America. We will definitely be staying here again!

Quick stats about vacation rentals that are kid-friendly in Sheboygan

  • Total rentals

    80 properties

  • Nightly prices starting at

    ﺩ.ﺇ147 before taxes and fees

  • Total number of reviews

    4.6K reviews

  • Family-friendly rentals

    70 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

Destinations to explore