
Holiday rentals with outdoor seating in Sheboygan County
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Sheboygan County
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Sheboygan County outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Lakefront Blue Dune Cottage on Lake Michigan.
I can't say enough about this beautiful lake house! Greta is one of the finest hosts that I've ever come across. Timely information, quick responses, and there are so many extras!! So many toiletries, pantry, and fridge items for your comfort and convenience. We visited in October, so didn't need them, but a caddy by the rear door with suntan lotion and beach towels. Just an extremely considerate person. We enjoyed our stay very much and would love to return in the future.

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!

The 2400 sq ft Plymouth Paddock near Road America!
This is our second time staying at Eric and Anna's place. They are perfect hosts! Their place is perfect, clean, roomy and just a stones throw from downtown Plymouth and Road America. We will be booking again! Thank you so much!

Beach Break - Historic Home Meets Modern Comfort
Very clean, comfortable and quiet! Location was perfect. Missy responded to questions almost immediately. And had great suggestions for food and entertainment.

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!

Private Home 4 BR+2Ba, Heated Pool by Road America
Very nice house, ideal for us coming to town. We were 2 families with 4 kids and the place was the perfect size and convenient for all. The hot tub is a great addition, right next to the backdoor deck, very close actually from the house. Very clean and very flexible hosts, kitchen was great and the large dining table is perfect for 8 guests.

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!

Stay at Sunrise LLC, Like being at Grandma's
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.
Apartment rentals with outdoor seating

Home away from home
What a gem! I truly think this property is highly undervalued. The grounds alone are magnificent. Such a gorgeous historic home and peaceful neighborhood. It felt private and secluded yet close to everything that we needed to get to and very walkable safe area. I cannot say enough good things about this Airbnb and hope to stay there again on future trips! Thank you to our wonderful Host, Julie, who was responsive, kind, and very accommodating of us.

Helene's room
We absolutely loved our stay! Our first time at a bed and breakfast! Can’t say enough about how great Ashley was! She greeted us upon our arrival and gave us a tour of the property. We got up early for a fishing trip and she had set us aside a breakfast to go and the second day brought us breakfast to our room! She gave great fish fry recommendations as well! We loved having the lake view from our room!

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!

Country Apartment
Great place! Peaceful, country setting with places to eat within a short drive! It was super quiet! Would stay again!

Terrace View a Charming 1 Bedroom Apt
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.

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan
Great stay. Great communication. Great accommodations. Chris is an excellent host.

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!

Private Retreat near Road America and Elkhart Lake
Had a long weekend at Road America so wanted to stay close so I could get back and forth during the day. This place was a perfect fit. Like 7-8 minutes to the track and the perfect amount of space. Nice and quiet so I could sleep with the countryside right outside the door. Btw, love that bench by the door. Perfect spot to sit and take my shoes off and park my backpack. You’re 5-10 minutes from downtown Plymouth and Elkhart Lake. Dozens of restaurants, stores and whatever else you need. Great place!
Condo rentals with outdoor seating

Modern 2 Bedroom Condo with Lake Michigan View
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.

A Glorious Getaway Sheboygan - LUX Lake Condo
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

Modern South Pier Condo on Sheboygan River!
Beautiful condo with well stocked kitchen, very nice bathrooms and great walkable location!!

Heavenly Condo in the Malibu of the Midwest
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.

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

Janelle's Dockside Condo
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.

Adorable modern cottage-upper unit
We enjoyed our stay. She was very responsive and the location can't be located in a better spot. Will definitely stay again.

Beachside Lake View - 2br - First Floor - Garage
Beautiful location. Everything was great from the beginning to the end of our stay. We can’t wait to go back for another stay.
Destinations to explore
- Apartment rentals Sheboygan County
- Rentals with a kayak Sheboygan County
- Pet-friendly rentals Sheboygan County
- Condo rentals Sheboygan County
- Rentals with a patio Sheboygan County
- Rentals with breakfast Sheboygan County
- Kid-friendly rentals Sheboygan County
- Rentals with beach access Sheboygan County
- Rentals with a fire pit Sheboygan County
- Rentals with lake access Sheboygan County
- Rentals with a fireplace Sheboygan County
- Beachfront rentals Sheboygan County
- Rentals with a washing machine and dryer Sheboygan County
- Rentals with a hot tub Sheboygan County
- Rentals with outdoor seating Wisconsin
- Rentals with outdoor seating United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Erin Hills Golf Course
- Milwaukee Public Museum
- Kohler-Andrae State Park
- Whistling Straits Golf Course
- Bradford Beach
- Harrington Beach State Park
- Milwaukee Country Club
- The Bull at Pinehurst Farms Golf Course
- West Bend Country Club
- Trout Springs Winery
- Pine Hills Country Club
- Heiliger Huegel Ski Club
- Discovery World
- Sunburst
- Blue Mound Golf and Country Club