Vacation rentals with outdoor seating in Sheboygan

Find and book unique outdoor seating rentals on Airbnb

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Popular amenities for Sheboygan outdoor seating rentals

House rentals with outdoor seating

Top guest favorite
Home in Sheboygan
5 out of 5 average rating, 20 reviews

Norwind Ranch - Peaceful Retreat Near Road America

MichaelRating, 5 stars7 months ago
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!
Top guest favorite
Home in Plymouth
4.97 out of 5 average rating, 174 reviews

The 2400 sq ft Plymouth Paddock near Road America!

DanRating, 5 stars4 weeks ago
Our family has stayed in several rental homes and this property definitely stood out as one of the best we have ever stayed at. The house was very clean. The owners have thought of everything. Lots of games and fun things for the kids to do, extra toiletries ,( toothpaste, toothbrushes, shaving cream, razors and soap and shampoo in every bathroom. Local samples of food n the fridge, beer, wine, pop, cheese, and coffee. We would definitely stay their again.
Guest favorite
Home in North Point
4.91 out of 5 average rating, 11 reviews

Beach Break - Historic Home Meets Modern Comfort

GaryRating, 5 stars3 months ago
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.
Guest favorite
Home in Plymouth
4.94 out of 5 average rating, 469 reviews

Country Guest House - Beautiful Gardens!

JeffRating, 5 stars2 weeks ago
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!!
Top guest favorite
Home in Glenbeulah
4.98 out of 5 average rating, 129 reviews

Stay at Sunrise LLC, Like being at Grandma's

GeorgeRating, 5 stars1 week ago
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.
Top guest favorite
Home in Sheboygan Falls
4.99 out of 5 average rating, 88 reviews

Adorable bungalow in historic Sheboygan Falls,WI

LaurenRating, 5 stars2 weeks ago
Loved our stay! Super clean and comfortable. The basement games were a fun perk. 10/10 would stay at Neil’s again!
Top guest favorite
Home in Oostburg
4.96 out of 5 average rating, 187 reviews

Shamba on the Lake, Oostburg, WI

SandyRating, 5 stars1 month ago
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.
Top guest favorite
Home in Campbellsport
4.99 out of 5 average rating, 174 reviews

Gleason's Chouse

ReneeRating, 5 stars1 week ago
We loved the church! It is a very large space and has everything one might need. The neighborhood is nice and quiet and there are lots of little towns not too far away. We highly recommend this Chouse. Thanks!!

Apartment rentals with outdoor seating

Top guest favorite
Apartment in Kewaskum
5 out of 5 average rating, 19 reviews

Local Landmark / Coffeehouse / Kettle Moraine

DougRating, 5 stars1 week ago
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.
Guest favorite
Apartment in Sheboygan
4.88 out of 5 average rating, 8 reviews

Cactus Corner KING Apartment

JessRating, 5 stars10 months ago
We enjoyed our stay. It was clean just like the photos.
Top guest favorite
Apartment in Port Washington
4.96 out of 5 average rating, 327 reviews

Grace Adventure House, walk to Port, Shops, Beach

BarbaraRating, 5 stars1 week ago
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.
Superhost
Apartment in Port Washington
4.82 out of 5 average rating, 33 reviews

Unique 1-bed apartment

SarahRating, 5 stars1 day ago
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.
Top guest favorite
Apartment in Port Washington
4.95 out of 5 average rating, 279 reviews

Silvers Four-Six-Four *A home away from home*

IsabelleRating, 5 stars1 week ago
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!!
Guest favorite
Apartment in Elkhart Lake
4.95 out of 5 average rating, 144 reviews

Schoolhouse Straight Inn

CandyRating, 5 stars1 month ago
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.
Superhost
Apartment in Sheboygan
4.6 out of 5 average rating, 15 reviews

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan

ClaudiaRating, 5 stars5 days ago
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!
Top guest favorite
Apartment in Port Washington
4.97 out of 5 average rating, 186 reviews

Inn on Billy Goat Hill

TjRating, 5 stars3 weeks ago
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

Condo in South Pier
4.69 out of 5 average rating, 13 reviews

Modern 2 Bedroom Condo with Lake Michigan View

JoeRating, 5 stars10 months ago
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.
Top guest favorite
Condo in South Pier
4.98 out of 5 average rating, 43 reviews

A Glorious Getaway Sheboygan - LUX Lake Condo

SallyRating, 5 stars1 day ago
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
Condo in South Pier
4.8 out of 5 average rating, 15 reviews

Modern South Pier Condo on Sheboygan River!

BrendaRating, 5 stars1 week ago
Beautiful condo with well stocked kitchen, very nice bathrooms and great walkable location!!
Guest favorite
Condo in South Pier
4.97 out of 5 average rating, 31 reviews

Heavenly Condo in the Malibu of the Midwest

LisaRating, 5 stars3 months ago
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.
Top guest favorite
Condo in South Pier
4.98 out of 5 average rating, 41 reviews

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

BenRating, 5 stars1 week ago
Awesome place!
Guest favorite
Condo in South Pier
4.93 out of 5 average rating, 89 reviews

Janelle's Dockside Condo

KathleenRating, 5 stars1 week ago
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.
Top guest favorite
Condo in Elkhart Lake
5 out of 5 average rating, 12 reviews

Adorable modern cottage-upper unit

AntonioRating, 5 stars10 months ago
We enjoyed our stay. She was very responsive and the location can't be located in a better spot. Will definitely stay again.
Guest favorite
Condo in Sheboygan
4.88 out of 5 average rating, 206 reviews

Beachside Lake View - 2br - First Floor - Garage

RobinRating, 5 stars7 months ago
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

    G$8,394 GYD 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