Kid-friendly vacation rentals in Sheboygan

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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 stars8 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.
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
4.96 out of 5 average rating, 225 reviews

Dog Friendly Blue Door Cottage / Fully Fenced Yard

DebbieRating, 5 stars1 week ago
This place was just what our family needed. It was wonderful to bring our dog Annabelle and explore the Sheboygan area. We used the coffee bar and did the wine exchange and the place felt like "home"! I would highly recommend for a home like atmosphere and spending quality time together. We hope to visit again when the weather is warm to swim in what looks like beautiful beaches. Thank you for your hospitality!
Top guest favorite
An arcade game cabinet is positioned near the entrance, featuring a vibrant design and labels for various classic games, such as Asteroids and Pac-Man. Natural light streams in through the window beside it, illuminating the wood-paneled walls and tiled flooring.
Home in Sheboygan
5 out of 5 average rating, 27 reviews

Private 3 bd country home 2 miles N of Kohler WI

JanetRating, 5 stars8 months ago
The perfect location and house for our visit to Wisconsin for a wedding! We loved the house, it had everything we needed for our stay. Coming from a rural area the location made us feel like being at home. The grandkids enjoyed the backyard, complete with games for them to play and room to run. There was plenty of room and seating outside to sit back and enjoy the cooler weather and sunrise. Shelly was quick to respond to questions and was a great host. If ever back in Wisconsin would definitely stay here again!

Kid-friendly apartment rentals

Top guest favorite
A cozy living area showcases a flat-screen television mounted above a vintage wooden dresser. An elegant fireplace with detailed woodwork is positioned nearby, complemented by wooden flooring. Decorative items are arranged on the mantel, enhancing the room's charm.
Apartment in Waldo
4.98 out of 5 average rating, 278 reviews

The Blue Cobb House

MikeRating, 5 stars3 days ago
My wife and I were celebrating our 45th Wedding Anniversary- Jewel made it so special for us! And her place? WOW! We’ve stayed in AirBnb’s from Olympia to Siesta Key, from Zagreb to Dubrovnik- and Jewel’s place and her hospitality outshines them all! Beautiful accommodations, spotless, every possible provision, comfortable and supportive bed, - it was simply heavenly!!! Thanks to Jewel!!!
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, 301 reviews

Pineyard Plymouth Apartment

AbbyRating, 5 stars3 days ago
Very comfortable and clean. No frills as advertised and priced. Road America is 7 minutes down the road so no complaints here.
Guest favorite
A bright living area features a large window allowing natural light to fill the space. Seating includes two chairs with light wood frames and a yellow couch. A small coffee table sits on a textured rug, accompanied by a tall plant adding a touch of greenery.
Apartment in Sheboygan
4.84 out of 5 average rating, 25 reviews

2BR Apt Near Beach & Downtown

DillonRating, 5 stars4 days ago
Hosts were great. Place was clean! Great first experience using Air B&B would definitely stay again!
Top guest favorite
A spacious seating area is highlighted by a grey leather sofa with decorative cushions. A round grey ottoman sits at the center on a textured area rug, while a small side table displays books and a bowl. A vintage photograph adorns the wall, complemented by a floor lamp.
Apartment in Elkhart Lake
4.96 out of 5 average rating, 142 reviews

Schoolhouse Straight Inn

CandyRating, 5 stars2 days ago
We needed a dog friendly place for a Road America weekend. This was great. I walked the dog nearby and across the road to a beautiful lakefront neighborhood. Didn’t cook there but heated up takeout food. Cute backyard that was too wet for us to hang out in. Comfy beds and cool race memorabilia in unit.
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, 158 reviews

Modern Upstairs Apt - Steps from Lake Michigan

SamRating, 5 stars1 week 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!
Guest favorite
An open living space features a round dining table with four chairs, complemented by a cozy seating area with a sofa adorned in warm tones. Natural light filters through large windows, while string lights add a gentle illumination to the ceiling.
Apartment in Sheboygan
4.89 out of 5 average rating, 9 reviews

Parkside Studio Apartment

TomRating, 5 stars4 days ago
Ashlynn was very kind and helpful. We arrived late at somehow the code wasn’t working for us but thankfully she was alerted to it and was able to assist. I felt badly about waking her up but she was so kind about it. The place was beautiful and bed was great. If in the area definitely a great spot to stay.
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 stars1 week 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!
Guest favorite
A charming two-story house features a welcoming front porch with white railings. American flags adorn the porch, while potted plants add a touch of greenery. The exterior is clad in light siding, with large windows allowing natural light to enter the home.
Apartment in Sheboygan
4.92 out of 5 average rating, 66 reviews

Entire Upper Rental Unit-South Central Sheboygan

EricaRating, 5 stars6 months ago
The apartment was easy to get to, very clean, and in a great location in town. Sarah was very responsive and helpful.

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 stars2 weeks 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, 37 reviews

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

KateRating, 5 stars2 weeks 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 stars3 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

    $40 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