
Vacation rentals with outdoor seating in Sheboygan
Find and book unique outdoor seating rentals on Airbnb
Top-rated outdoor seating rentals in Sheboygan
Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.
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Popular amenities for Sheboygan outdoor seating rentals
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.

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!

Country Guest House - Beautiful Gardens!
Looking for a place to stay when we visited our kids for the weekend. Lots of room for the dogs to run and played pool and air hockey. Great place!!

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.

Luxury 4B-2Ba Lake & Beach House
This was my second work trip this year to Sheboygan from Portland, OR, and my second time staying in Brenda and Brian's absolutely lovely home. Each time I've brought 3 colleagues with me, and we've decided it's the only place we ever want to stay while in town. It's beautifully and luxuriously updated while also being super comfy, in an quiet and quaint neighborhood just a block from the beach and minutes away from the city's charming attractions and perfect home base for exploring the region. We stayed nearly a week this time out, giving us time to truly appreciate all the thoughtful details that make the home so special. Brenda is such a gracious and personable host, generously offering insider's tips on best places for food and shopping. Sheboygan is a lovely city, can't imagine a better place to enjoy time there for work or leisure. Highly recommended. Thanks again, Brenda!

HOT TUB~KingBed~PoolTable~PokerTable~BatmanMovieRm
Excellent getaway the place. The area has good restaurants nearby as well. The house has ample amenities to use! This house is a plus if you are a batman fan!!

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.

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!
Apartment rentals with outdoor seating

Local Landmark / Coffeehouse / Kettle Moraine
Great location in town, coffee shop right below the apartment was a nice touch. Jessica and Troy provided tons of recommendations for things to do and see in the area. They made it feel very much like a home away from home! Would highly recommend.

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

Grace Adventure House, walk to Port, Shops, Beach
Dave’s place is amazing. The Airbnb’s location is great very close to many restaurants, parks, trails and the marina. Beautiful location! The apartment was very comfortable for our family of four (two adults and two children). We felt at home with many amenities. The shower and bathroom was beautiful and comfortable. The kitchen had all the utensils, pots and dishes to make home cooked meals. We enjoyed playing board games and having wonderful family meals in the large dining room. The home was equipped with everything we needed and much more making our stay comfortable and relaxing. Dave and his family are very sweet and welcoming hosts. I will definitely be returning and recommending the Airbnb to our friends.

Unique 1-bed apartment
Julie’s place was quiet and peaceful for a quick getaway to Port Washington! She was very friendly and kind to my dog, and made me feel right at home as a solo traveler. Would recommend to anyone visiting the area who prefers to be away from the hustle and bustle of a big city.

Silvers Four-Six-Four *A home away from home*
Such a wonderful stay! The apartment was extremely neat, tidy and perfect for our needs! My friend and I are on the taller side, so next time we’ll stay on the lower level, assuming the ceilings are slightly higher. But regardless, next time we’re in Port, we’re staying with Elle!! Thank you again for a great stay!!

Schoolhouse Straight Inn
We needed a dog friendly place for a Road America weekend. This was great. I walked the dog nearby and across the road to a beautiful lakefront neighborhood. Didn’t cook there but heated up takeout food. Cute backyard that was too wet for us to hang out in. Comfy beds and cool race memorabilia in unit.

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!

Inn on Billy Goat Hill
Cannot say enough good things about our stay at Billy Goat Hill! Fantastic location with a quick walk to the local shops, parks, and restaurants. The space was incredibly cozy and had everything you could need for your stay. Extremely affordable for a weekend getaway. Donna and Paul were so inviting and responsive. Cannot wait to return and visit 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 vacation rentals with outdoor seating in Sheboygan
Total rentals
120 properties
Nightly prices starting at
ﺩ.ﺇ147 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
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- Erin Hills Golf Course
- Kohler-Andrae State Park
- Whistling Straits Golf Course
- Bradford Beach
- Harrington Beach State Park
- Milwaukee Country Club
- The Bull at Pinehurst Farms Golf Course
- Trout Springs Winery
- West Bend Country Club
- Heiliger Huegel Ski Club
- Pine Hills Country Club
- Green Bay Country Club Sports Center
- Sunburst
- Blue Mound Golf and Country Club
- Pollock Community Water Park