
Holiday rentals with outdoor seating in Sheboygan
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Sheboygan
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 outdoor seating rentals
Holiday House Rentals with Outdoor Seating

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
Such a great place to stay. The neighborhood is peaceful and the home's architecture reminds me of houses from my childhood. Missy is also an excellent and proactive host. I'm looking forward to staying here again, soon.

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!

Stay at Sunrise LLC, Like being at Grandma's
Dean and Kaye are great hosts. They were very accommodating and helpful. The property was just as it is in the listing. We had everything we needed and more. I plan on returning again next year.

Wyatt's Country Home - King Bed
We stayed here for a golf trip and could not have been more pleased! We've stayed in a lot of places, but this one was the best, by far!!! Alyssa was always quick to answer any question I had and made sure we had everything we needed. We had plenty of room and I only wish we had more time there. Thank you!!

Shamba on the Lake, Oostburg, WI
We have stayed at Shamba 4 times. It is an absolutely amazing spot on Lake Michigan. The home is lovely and very spacious. You could not ask for better views of the lake from inside or outside. The beach is literally right outside your door. Great spot for kids to play and great for walks too. Will definitely return again.

Gleason's Chouse
A very unique place with a definite sense of history. Very friendly, welcoming, and helpful hosts. We liked it and recommend it to anyone looking for a quiet area to stay in.

Sheboygan's Great Lake's House
The home is clean, comfortable, and very pet friendly. The kitchen is well equipped. The deck is shady and comfortable. The hosts communicated very well and were very welcoming. The location is great. I definitely recommend this home and hope to return.
Apartment rentals with outdoor seating

Local Landmark / Coffeehouse / Kettle Moraine
The hosts were both helpful and communicated readily about the area...giving good info on local restaurants and places to visit. They also responded in a timely way if I had any needs. Lovely room, looks newly renovated! Thank you for a pleasant stay!

Cactus Corner KING Apartment
We enjoyed our stay. It was clean just like the photos.

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.

Schoolhouse Straight Inn
Great host - great amenities that I didn’t even get to use. Next time!

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan
Chris was a great host! Our other Airbnb didn’t respond to us and he was able to get us in with a same day reservation! He was very friendly, brought us a high chair and provided some local snacks for our stay! The house was spotless and the backyard and neighborhood were so cute! We will be staying with you again next time we’re in Sheboygan!

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!

The Cozy Country Farmhouse, Eisenbahn Suite
Connie and rich were amazing host . They showed love and kindness to us . If I need a place in kewaskum again i definitely would rent the place out again . Very beautiful place !

Spacious Studio Apt walking distance to RD America
Beautiful condo. Would absolutely stay here again!
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.
Quick stats about holiday rentals with outdoor seating in Sheboygan
Total rentals
120 properties
Nightly prices starting at
$62 AUD before taxes and fees
Total number of reviews
7K reviews
Family-friendly rentals
100 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Destinations to explore
- Rentals with a patio Sheboygan
- Rentals with a fire pit Sheboygan
- Kid-friendly rentals Sheboygan
- Apartment rentals Sheboygan
- Rentals with lake access Sheboygan
- Rentals with a fireplace Sheboygan
- Rentals with beach access Sheboygan
- Rentals with a washing machine and dryer Sheboygan
- Condo rentals Sheboygan
- Pet-friendly rentals Sheboygan
- Rentals with outdoor seating 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
- 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