
Pet-friendly holiday rentals in Sheboygan
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Top-rated pet-friendly home rentals in Sheboygan
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Popular amenities for Sheboygan pet-friendly home rentals
Pet-friendly house rentals

Sleeps 7{SPACIOUS}Pets Welcome!
they were a great host I felt right at home I give them a 5 star the place was very clean I would recommend them if you are looking for a Airbnb

Norwind Ranch - Peaceful Retreat Near Road America
Flew in for business with Acuity Insurance. Perfect place to stay. Drove up to Green Bay for the Texans vs. Packers game. Only an hour drive from the house in Sheboygan. I will definitely stay here again when I come back to town!

Newly Renovated Beach Front Home in Oostburg WI
Our family stayed with our good friends for a long weekend for a total of 9 including our kids. The house layout worked out well to have our family of four on the upper level and our friend’s family of five on the lower level to give each other some privacy when needed. The sunroom on the upper level is beautiful and it was lovely for watching the sunrise! There was room for everyone at meal time and we felt we had everything we needed to eat in each night. The water pressure in the bathrooms worked well and we managed without a bath tub for the littles. The highlight was the beach where the kids enjoyed hours in the sand. It was very private and quiet, perfect for walks on the beach. Lastly, we picked the location as it was near the Kohler Andre State Park and near Sheboygan where we spent the morning at the water park. Overall an enjoyable trip!

3-bdrm beachfront home on Lake Mich, Sheboygan WI
Now that I have stayed at Jack's home @ 5 times, I can easily verify that every moment spent in that home is magical - steps away from a walk on the beach, the methodical waves lapping on the shoreline, and the majestic sunrises reflecting on the water combine to provide a therapeutic sensory experience that delivers 24 hours each day. If that isn't enough, there are fabulous coffee shops, restaurants, and bars that you can walk to as well as many others a short drive away. No - Jack does not pay me to write these reviews ... the reviews write themselves. Enjoy!

House Near the Lake
Great place to stay. Everything was as stated in the ad. Would definitely stay there again.

SurfDaze! A Lake Michigan property
This was the perfect getaway to enjoy the gorgeous scenery with the dogs. Cassandra was very responsive and everything was easy from booking to departure. Would definitely go back!

The Suncatcher -Steps from Lake - Fenced Yard
The house was perfect for our trip. It looked exactly like the photos. The house was well stocked with everything we needed and was very clean and comfy. We especially appreciated all the stuff geared towards kids. We had 3 little ones who enjoyed all the toys, activities and backyard. Jessica was very responsive and helpful! We would love to stay there again!

Wake on the Lake - Minutes to Whistling Straights
We had the best time at Brian's house and highly recommend it! We gathered with our young adult kids for several days and the house accommodated all 7 of us quite easily. The beds are comfortable and the house is spacious with thoughtful, peaceful decor. The kitchen was well stocked and there was plenty of seating for family dinners. The living room had ample seating for movie nights, and while the internet was a little on the slow side, it was sufficient for streaming movies. The best part of the house is its secluded location and gorgeous lake views out the numerous windows. We would definitely stay here again if we were in the area. The host was so kind and responsive and even left us a tray of locally made chocolates and taffy with a sweet note! They went above and beyond!
Pet-friendly home rentals with a pool

Breezy Acre...Relaxing small family get a way.
Kelly and Don's property is so beautiful and peaceful. It is quiet and relaxing. The pool and hot tub were a nice relief getting away from the city. There were a ton of stars out at night and the moon was bright. Kelly and Don were super responsive and friendly. I would recommend this place to anyone!

Stay in the heart of Elkhart Lake at Victorian Inn Resort
Melissa’s place was exactly as described and perfect our weekend getaway. Melissa was extremely responsive and accommodating. We will definitely stay here again! We loved it! Our littles didn’t want to leave either and ask when we can go back to our room in the big white house!

Country Cottage Indoor Pool HOT TUB NFL Draft ava
Great stay! My group loved it and had a blast. House was Beautiful & Host was GREAT, was very understanding and helpful. DEFINITELY recommend and would love another stay sometime.

Resort Life 2 Queen Suite
Great place in the heart of Elkhart Lake. Close to restaurants and an easy drive to Road America.

Resort Condo on Elkhart Lake
Great stay on Elkhart Lake! Located in a central location, you can walk into town for dinner and also great lake amenities right on site. We rented a boat for the day and enjoyed the pool and beach access. We also greatly appreciate Pam being one of the few places we found that is dog friendly!

First Floor Queen with Single Pull-out
A very nice experience overall. Very responsive with questions and the location is very convenient for swimming, ice cream, getting on the lake, etc.

Sleeps 8! 2 Full Bath with Kitchenette!

1st Floor Double Suite Courtyard View
Private, pet-friendly home rentals

Cozy cabin in the woods
Great place, great location, and no doubt our go to place when in town working. I highly recommend!

Cabin moments away from Road America and Lakes
Jeanette’s cabin was perfect for our couples trip to the Road America track. Close to everything and very peaceful at night! Jeanette was very accommodating and we had everything we needed for our stay.

Parkside Retreat | Minutes from Elkhart Lake
This place is a hidden gem for air bnbs. They had so much to offer and went above and beyond to even suggest places to eat! The place was so clean and was an amazing experience.

Private 3 bedroom lake house
Awesome place. We will be back!

Turn 15 Lodge near Road America
Turn 15 is convenient and an easy place to stay. There are plenty of activities at the house, and it’s not a long drive to the track and town.

Rustic Chic Cabin in Kettle Moraine
Title: A Perfect Getaway in the Woods 🌲✨ We had an incredible stay at this beautiful cabin in the woods. From the moment we arrived, we were impressed by how thoughtfully everything was prepared. The cabin itself was even more stunning than the pictures—immaculately clean, beautifully decorated, and full of cozy touches that made it feel like home. The surroundings were peaceful and private, with nature all around. We especially loved winding down by the fire in the evening. It truly felt like a retreat from everyday life. The host was responsive, kind, and made sure we had everything we needed for a comfortable stay. If you’re looking for a serene and charming place to unwind, this cabin is it. We’re already thinking about our next visit!

Lake Front Cottage With Dock. Walk to Road America
We had a wonderful stay at Robert’s lakefront cottage! The place was peaceful, clean, and had everything we needed for a relaxing weekend getaway. The view of the lake was beautiful, and we really enjoyed the cozy atmosphere. Robert was a fantastic host – communicative, helpful, and very easy to reach if we had any questions. Check-in was smooth and everything was exactly as described. We would definitely recommend this place to anyone looking for a quiet escape, and we’d love to come back in the future. Thank you for hosting us!

Feel at home in this 3 bedroom, 2 bath home.
Felt like we were staying at a family members home. Very cozy and peaceful setting. We brought our dogs and they loved the large and fenced backyard. Plenty of space in the large bedrooms and living room. Kitchen had everything you could possibly need to cook anything you wanted. Host provided thoughtful treats for the dogs, and beverages and coffee. Even had prepared ice balls for beverages that was a nice touch. We loved our stay, worked great for our needs and would return again in the future if needed.
Quick stats about holiday rentals that are pet-friendly in Sheboygan
Total rentals
70 properties
Nightly prices starting at
$92 AUD before taxes and fees
Total number of reviews
3.8K reviews
Family-friendly rentals
60 properties are a good fit for families
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Wi-Fi availability
70 properties include access to Wi-Fi
Destinations to explore
- Rentals with a patio Sheboygan
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- Erin Hills Golf Course
- Kohler-Andrae State Park
- Whistling Straits Golf Course
- Bradford Beach
- Milwaukee Country Club
- The Bull at Pinehurst Farms Golf Course
- Harrington Beach State Park
- Trout Springs Winery
- Heiliger Huegel Ski Club
- West Bend Country Club
- Pine Hills Country Club
- Green Bay Country Club Sports Center
- Blue Mound Golf and Country Club
- Sunburst
- Pollock Community Water Park