Kid-friendly holiday rentals in Sheboygan County

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!

Thank you Todd for a wonderful stay! Our group really enjoyed the property and selection of board games to play! Very convenient location to local spots and restaurants. Very simple and direct check in/out progress and great communication. Would love to stay here again if I’m ever in the area!

Beautiful, well-appointed home with a heck of a view AND walking distance to downtown. Tricia was communicative and kind. Great experience!

Charming country home which was a great place for us to relax after attending the races at Road America all day. Very clean and had everything we needed.

Jaclyn is an amazing host. She really cares about the needs of her guest and it showed by the little touches she did to make us feel so at home and so comfortable and the neighbors were also friendly and welcoming. I highly recommend this place and Jaclyn as a host. I can only hope when we return to the area this place will be available.. Jaclyn thanks for making us feel so at home and spoiling us with the little touches you provided for our stay...... Pam

We stayed for a week and felt right at home! It was spacious, well maintained and decorated, and had more than we needed. We especially loved the fenced in yard with decorative pond and the game room downstairs. We would definitely stay here again.

This is my favorite place to stay in the area. The property is beautiful and it is so quiet. We enjoyed a bonfire!

The host was very nice and a nice place to stay. Very clean and very close to the beach

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!!!

Missy and Kyle's apartment in Sheboygan was truly a great recombobulation station! The location was spectacular with only two blocks to Lake Michigan in one direction and two blocks to great dining, farmers market, coffee shops, and local shopping in the other direction. The apartment was incredibly clean, cozy, and comfortable for some rest and relaxation in-between our local adventures. It was a lovely home away from home with everything you would need to prepare meals. And in the event you've forgotten something at home, there is a good chance Missy has thought about it for you.

This is such a gem! We traveled with 2 young children and after a day at Road America it was EVERYTHING we needed. We didn’t get a chance to try to sauna or cold plunge, but the place felt just like home and was so convenient. We can wait to visit again!

Doug was an excellent host making sure everything was perfect during my stay if im ever in Sheboygan again I’ll definitely be staying here again.

Great stay. Great communication. Great accommodations. Chris is an excellent host.

The only place we stay when we're in town! Great to be back in our little home away from home.

Thank you for hosting us. It was exactly what we needed to rest and be ready to go to our daughter’s baby shower the next day.

This place was absolutely perfect and I will definitely stay again when back in Sheboygan. It’s a short walk to Lake Michigan and perfect for a nice evening stroll to downtown for dinner. Great place and just what I needed!

Brian’s instructions to check in was very good. The condo was very clean and the views were great. Short walks to great restaurants and the beach. Every night we ended our day sitting on the patio looking out at the lake. Definitely a place I’d rent again when I visit Sheboygan.

The accommodations were perfect for a large gathering. Lots to see and do just within walking distance. Beautiful location and the space was perfect for our family gathering. Great home with all you needs. Lovely bedrooms with very comfortable beds. Great time was had here Sally

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.

We absolutely loved our location so close to the beach and harbor area! We had everything needed for our stay. There is the perfect little ice cream shop a block away! Parking on the street available right in front of where we stayed. There is a book in the apartment with comments from previous guests with notes on great things they discovered while there as well. We contributed before our departure. We would absolutely consider another stay in the future if we visited again. Sheboygin is a beautiful place. Park across the street made it so easy to see out and over the harbor providing a great view allowing for a great walk to see things. Definitely a "10" in our books!

Janelle’s place was spacious and sparkling clean. The location is great, right on the river and an easy walk to the lake. We would definitely stay again if we come back to Sheboygan.

Very cool and well themed condo situated right between downtown Elkhart Lake and Road America. Was perfect for our group of 4. We would definitely recommend!

Beautiful location. Everything was great from the beginning to the end of our stay. We can’t wait to go back for another stay.

Had a wonderful stay. The location was perfect for us. Loved the restaurants that we could walk to.