
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!
There were no mice or roaches. There was not any kind of sticky goo on the floor or in the sinks. Everything was clean! The dishes were especially spotless. The refrigerator cold our food perfectly. The televisions in each room had crystal clear high definition and excellent sound quality. We baked cookies in the oven and they turned out great. I overcooked a pizza and the smoke detector was fully functional and might have saved our lives. We felt secure and safe with a numeric door lock where only we knew the secret code. The beds were soft and comfortable. I would highly recommend this property to anyone. If you like living the dream this is the place for you!

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!

Spacious Home Near Lake MI w/ Fire Pit
We had a great stay! Check in and out were simple, the home was immaculate, and the hosts are very responsive. We look forward to staying again!

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!

The Asher - A Designer Lake Michigan Retreat
We ones the sound of the waves. We were at home from the minute we walked in. We walked the beaches and grilled terrific dinners. The kitchen was fully stocked and the home was neat and clean. The amount of light that came in the home and view of the water was breathtaking. The bedrooms were roomy and beds were super comfortable. We loved every minute of our stay and will be back again soon. Sara, our host, was amazing and very responsive. She has created an absolute sanctuary.

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.

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.

Beautiful Home Near Lake Michigan & Downtown
We have stayed at Jocelyn's now 4 times so we knew we were getting a great "home" away from home. I highly recommend a stay at Jocelyn's you will not be disappointed.
Pet-friendly home rentals with a pool

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!

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.

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 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!
Private, pet-friendly home rentals

Quiet Country Charm
Would absolutely stay here again! Beautiful barn, Terese was so friendly, got to visit the goats and two adorable kittens, and very peaceful. The loft smelt very nice and fresh, much better than I expected and was very clean! We were able to cook out on the grill outside of the barn and Terese was extremely helpful and responsive when we had questions.

Turn 15 Lodge near Road America
This was our first time racing at Road America and Dean and Lori's place was absolutely perfect. It is so close, you can actually walk over to the track in the nice weather, and there are plenty of other great areas to explore on foot as well! Their home is perfectly comfortable and enjoyable while being subtly themed with fun racing references. We will definitely be back to Road America, and plan to stay at this home every time possible. Thank you so much for making our first weekend here an enjoyable one!

Lakeside Cabin Retreat Relax at Private Lake House
My husband and I stayed here for a weekend in April. We enjoyed walking around the lake with our dog, and curling up to read afterwards in the cozy great room. The kitchen was well-stocked, as was the rest of the cabin. We especially liked how accessible Kohler, Sheboygan and Elkhart Lake were, with lots to do. Hope to come back!

Road America Treasure @ Elkhart Lake - 4 bedrooms
excellent host, very warm felt house, a place to relax and disconnect, thank you wendy

Lake Front Cottage With Dock. Walk to Road America
Nice place and nice people, would go back for any events I find myself at Road America.

SurfDaze! A Lake Michigan property
We had an incredible stay at SurfDaze! The pictures don’t do it justice—this is a truly stunning beachfront property on Lake Michigan. The home was spotless, beautifully maintained, and exceptionally comfortable. Waking up to the sound of the waves and enjoying the breathtaking views made our trip unforgettable. We can’t wait to come back!

Secluded Country Farm Getaway
Sarah has a great place in the country that allows you to get close to nature, while also staying comfortable in the camper with lots of amenities. Our daughter absolutely loved interacting with the chickens, goat and especially the cow. The hiking trails are great. Sarah is a welcoming host and went out of her way to make sure we had everything we needed for a fantastic visit!

Character filled 3 Bedroom Carriage House
The Carriage House is a cozy, welcoming space in an awesome location. We loved being able to walk to the beach, coffee shops, museums, and more. We appreciated all the thoughtful touches like plenty of lamps, blankets, and charging cords, and the wine and drink chips on arrival were so generous. The well-stocked kitchen had all the equipment we needed to make a few meals. The place was just the right size for our group of four adults, two kids, and a dog. Some of the furniture is on the shabby-chic end of things but we all found comfortable spots.
Quick stats about holiday rentals that are pet-friendly in Sheboygan
Total rentals
70 properties
Nightly prices starting at
£45 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
Wifi availability
70 properties include access to wifi
Destinations to explore
- Rentals with lake access Sheboygan
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- Kohler-Andrae State Park
- Erin Hills Golf Course
- Whistling Straits Golf Course
- Milwaukee Country Club
- The Bull at Pinehurst Farms Golf Course
- Harrington Beach State Park
- Heiliger Huegel Ski Club
- Trout Springs Winery
- Bradford Beach
- Pine Hills Country Club
- Pollock Community Water Park
- Sunburst
- West Bend Country Club
- Green Bay Country Club Sports Center
- Blue Mound Golf and Country Club