
Kid-friendly vacation 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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Popular amenities for Sheboygan kid-friendly rentals
Kid-friendly house rentals

Modern 5 Bedroom Getaway House
Location was perfect for what we had on our plans. I would definitely recommend BookWorm Gardens. My grandchildren enjoyed the variety of games provided.

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

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

Stay at Sunrise LLC, Like being at Grandma's
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.

The Suncatcher -Steps from Lake - Fenced Yard
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.

*Centrally Located and Updated* The Barrel House
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.

Wander Back Inn to Sheboygan
We had a great time at this place. Everything was as described. Very easy to work with and accommodating.

Dog Friendly Blue Door Cottage / Fully Fenced Yard
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

Pineyard Plymouth Apartment
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!

Grace Adventure House, walk to Port, Shops, Beach
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.

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

Homeport
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.

Modern Upstairs Apt - Steps from Lake Michigan
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!

Lovely modern two bedroom home with fire pit
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!

Inn on Billy Goat Hill
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!

Cozy Sheboygan Upper
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

Urban Townhouse
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.

A Glorious Getaway Sheboygan - LUX Lake Condo
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.

Modern South Pier Condo on Sheboygan River!
Nice, comfortable condo. Easy parking, elevator, cozy.

Heavenly Condo in the Malibu of the Midwest
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.

Ellis District Urban Lake Condo
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!

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

Janelle's Dockside Condo
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!

Car Condo Rental in Elkhart Lake
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
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- Kohler-Andrae State Park
- Whistling Straits Golf Course
- Erin Hills Golf Course
- Milwaukee Country Club
- The Bull at Pinehurst Farms Golf Course
- Harrington Beach State Park
- Heiliger Huegel Ski Club
- Bradford Beach
- Trout Springs Winery
- Pollock Community Water Park
- Sunburst
- West Bend Country Club
- Blue Mound Golf and Country Club
- Green Bay Country Club Sports Center
- Pine Hills Country Club