Holiday rentals with outdoor seating in Sheboygan

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

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Popular amenities for Sheboygan outdoor seating rentals

Holiday House Rentals with Outdoor Seating

Top Guest favourite
Home in Plymouth
4.97 out of 5 average rating, 175 reviews

The 2400 sq ft Plymouth Paddock near Road America!

EricRating, 5 stars5 days ago
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!
Guest favourite
Home in Sheboygan
4.91 out of 5 average rating, 11 reviews

Beach Break - Historic Home Meets Modern Comfort

GaryRating, 5 stars4 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 favourite
Home in Sheboygan
4.94 out of 5 average rating, 51 reviews

3-bdrm beachfront home on Lake Mich, Sheboygan WI

JohnRating, 5 stars7 months ago
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!
Top Guest favourite
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 favourite
Home in Plymouth
4.97 out of 5 average rating, 208 reviews

Wyatt's Country Home - King Bed

KevinRating, 5 stars1 week ago
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!!
Top Guest favourite
Home in Oostburg
4.96 out of 5 average rating, 187 reviews

Shamba on the Lake, Oostburg, WI

SandyRating, 5 stars2 months 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 favourite
Home in Campbellsport
4.99 out of 5 average rating, 176 reviews

Gleason's Chouse

GeorgeRating, 5 stars2 days ago
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.
Top Guest favourite
Home in Sheboygan
5 out of 5 average rating, 41 reviews

Sheboygan's Great Lake's House

MarthaRating, 5 stars4 days ago
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

Top Guest favourite
Apartment in Kewaskum
5 out of 5 average rating, 21 reviews

Local Landmark / Coffeehouse / Kettle Moraine

ChristineRating, 5 stars2 days ago
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!
Superhost
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.
Guest favourite
Apartment in Sheboygan
4.95 out of 5 average rating, 20 reviews

Home away from home

Kirsten Rating, 5 stars10 months ago
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.
Guest favourite
Apartment in Elkhart Lake
4.95 out of 5 average rating, 145 reviews

Schoolhouse Straight Inn

JaredRating, 5 stars1 week ago
Great host - great amenities that I didn’t even get to use. Next time!
Superhost
Apartment in Sheboygan
4.6 out of 5 average rating, 15 reviews

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan

ClaudiaRating, 5 stars1 week 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!
Guest favourite
Apartment in Sheboygan
4.95 out of 5 average rating, 57 reviews

North 7th Place - Spacious 2 Bedroom Lower Unit!

Shelley MRating, 5 stars2 months ago
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!
Guest favourite
Apartment in Kewaskum
4.96 out of 5 average rating, 48 reviews

The Cozy Country Farmhouse, Eisenbahn Suite

AprilRating, 5 stars2 months ago
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 !
Guest favourite
Apartment in Plymouth
5 out of 5 average rating, 22 reviews

Spacious Studio Apt walking distance to RD America

KatieRating, 5 stars1 week ago
Beautiful condo. Would absolutely stay here again!

Condo rentals with outdoor seating

Condo in Sheboygan
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 favourite
Condo in Sheboygan
4.98 out of 5 average rating, 43 reviews

A Glorious Getaway Sheboygan - LUX Lake Condo

SallyRating, 5 stars6 days 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 Sheboygan
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 favourite
Condo in Sheboygan
4.97 out of 5 average rating, 32 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 favourite
Condo in Sheboygan
4.98 out of 5 average rating, 41 reviews

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

BenRating, 5 stars2 weeks ago
Awesome place!
Guest favourite
Condo in Sheboygan
4.93 out of 5 average rating, 90 reviews

Janelle's Dockside Condo

KathleenRating, 5 stars2 weeks 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 favourite
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 favourite
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 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