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Holiday rentals with outdoor seating in Sheboygan County

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

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Popular amenities for Sheboygan County outdoor seating rentals

Holiday House Rentals with Outdoor Seating

Top Guest favourite
Home in Oostburg
5 out of 5 average rating, 34 reviews

Lakefront Blue Dune Cottage on Lake Michigan.

Katie Rating, 5 stars8 months ago
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.
Superhost
Home in Oostburg
4.78 out of 5 average rating, 143 reviews

Newly Renovated Beach Front Home in Oostburg WI

JulieRating, 5 stars3 weeks ago
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!
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 stars1 week 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
4.92 out of 5 average rating, 12 reviews

Beach Break - Historic Home Meets Modern Comfort

MargieRating, 5 stars3 months ago
Very clean, comfortable and quiet! Location was perfect. Missy responded to questions almost immediately. And had great suggestions for food and entertainment.
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 stars8 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!
Guest favourite
Home in Plymouth
4.97 out of 5 average rating, 33 reviews

Private Home 4 BR+2Ba, Heated Pool by Road America

FrancoisRating, 5 stars4 months ago
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.
Guest favourite
Home in Oostburg
5 out of 5 average rating, 14 reviews

SurfDaze! A Lake Michigan property

CrystalRating, 5 stars4 weeks ago
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!
Top Guest favourite
Home in Glenbeulah
4.98 out of 5 average rating, 130 reviews

Stay at Sunrise LLC, Like being at Grandma's

PattiRating, 5 stars2 weeks ago
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

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.
Apartment in Sheboygan
4.84 out of 5 average rating, 31 reviews

Helene's room

EmilyRating, 5 stars3 weeks ago
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!
Guest favourite
Apartment in Elkhart Lake
5 out of 5 average rating, 8 reviews

Resort Condo on Elkhart Lake

SamanthaRating, 5 stars10 months ago
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!
Apartment in Sheboygan Falls
4.92 out of 5 average rating, 12 reviews

Country Apartment

StaceyRating, 5 stars22 months ago
Great place! Peaceful, country setting with places to eat within a short drive! It was super quiet! Would stay again!
Superhost
Apartment in Sheboygan
5 out of 5 average rating, 10 reviews

Terrace View a Charming 1 Bedroom Apt

DonteRating, 5 stars30 months ago
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.
Superhost
Apartment in Sheboygan
4.63 out of 5 average rating, 16 reviews

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan

JeremyRating, 5 stars1 week ago
Great stay. Great communication. Great accommodations. Chris is an excellent host.
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 Plymouth
5 out of 5 average rating, 31 reviews

Private Retreat near Road America and Elkhart Lake

FrankRating, 5 stars9 months ago
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

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 stars2 weeks 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 stars2 weeks 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 stars4 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 stars3 weeks ago
Awesome place!
Guest favourite
Condo in Sheboygan
4.93 out of 5 average rating, 90 reviews

Janelle's Dockside Condo

KathleenRating, 5 stars3 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.

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