
Pet-friendly vacation rentals in Sheboygan County
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Top-rated pet-friendly home rentals in Sheboygan County
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Popular amenities for Sheboygan County 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 Links! - Luxury Golf Retreat
We were on a golf trip and this was the perfect house for a trip to Whistling Straights. The house is located nearly right in between the Straights/Irish Course and Black Wolf Run which just made every day convenient. The Garage was a great place to unwind, relive the day’s adventures and get some last minute practice in. Chris was very helpful, from letting us check in a bit early to answering the phone right away when we reached out; he was a tremendous host and I would highly recommend you spend your time in Sheboygan/Kohler at this rental!

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.
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.

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!

Sleeps 8! 2 Full Bath with Kitchenette!

1st Floor Double Suite Courtyard View

The Queen Victoria Two Queen Suite
Private, pet-friendly home rentals

Charming 2bd/2bath condo
Cheryl was very responsive.

Summit Ranch - Elkhart Lake/Road America- 3 mins
Great location for visiting Road America - just a few short minutes away! We loved watching the sunset and deer from the big front windows. Quick drive to Elkhart Lake for some good restaurants as well.

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!

North 7th Place - Spacious 2 Bedroom Lower Unit!
We stayed at Chris’s place to visit nearby family with our two children and dog. The apartment was perfect for us: comfy beds and sofas; well-stocked kitchen; loads of games and books for entertainment. Lake Michigan is blocks away, and we took several (longish) walks to the beach and downtown shopping. Chris was quick to return texts, and he was a great host. 10/10 would return!

Pet-Friendly Sheboygan Home, 1 Mi to Lake Michigan
If your in Sheboygan fora youth Soccer tournament, this is a great alternative to staying in a hotel. Great location relative to fields in Sheboygan and Sheboygan Falls

Casa De Bell - Monthly Rentals Available!
Wonderful place to stay and great communication. Definitely 10 of 10 would stay again .

Road America & Golf Retreat
Was a lot larger than photograph, bunkbed room were queen size beds very roomy, the room itself had more space than expected, the property had plenty of space to park lots of cars. Pretty much had everything you needed if you were living in that house.

Cozy Cottage just steps from Lake MI
A terrific location with perfect access to the water. With great decor and thoughtful touches offering lovely hospitality. We'd love to stay again
Destinations to explore
- Rentals with outdoor seating Sheboygan County
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- Erin Hills Golf Course
- Milwaukee Public Museum
- Kohler-Andrae State Park
- Whistling Straits Golf Course
- Bradford Beach
- Milwaukee Country Club
- Harrington Beach State Park
- The Bull at Pinehurst Farms Golf Course
- Trout Springs Winery
- Heiliger Huegel Ski Club
- West Bend Country Club
- Pine Hills Country Club
- Discovery World
- Sunburst
- Blue Mound Golf and Country Club