Vacation rentals with outdoor seating in Sheboygan County

Find and book unique outdoor seating rentals on Airbnb

Top-rated outdoor seating rentals in Sheboygan County

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Guest favorite

Rental unit in Sheboygan

4.97 out of 5 average rating, 139 reviews

Modern Upstairs Apt - Steps from Lake Michigan

Have you ever wondered what Lake Life is like? Here is your chance! This is 1 of 2 AirBnB units in this cute duplex Come stay in this beautiful upper apartment located just one block from Lake Michigan. Take a quick walk to the lake in the morning to jump on your fishing boat or take the family to the beach in the afternoon! Located close to shopping and many local bars and restaurants within walking distance. You'll find relaxation and a great time here at the heart of Sheboygan's Shoreline!

Guest favorite

Cabin in Elkhart Lake

4.99 out of 5 average rating, 237 reviews

Elkhart A-Frame, Wooded Retreat near Road America

The Elkhart A-Frame is an ideal location for the adventure seeker who wants a unique and private experience that is still close to all the action. The home sits on a wooded three-acre private retreat only about a mile from the village of Elkhart Lake, Road America, and Golf Courses. This unique cabin was built in the 1970's but has been recently renovated with a fun Scandinavian modern flair. It has all the amenities for a memorable vacation stay that provides plenty of epic photo opportunities.

Guest favorite

Cottage in Oostburg

4.97 out of 5 average rating, 261 reviews

Sandalwood Cottage - 300 Feet From Lake Michigan

A HIDEAWAY one mile East of I-43 nestled in beautiful wooded acreage across from Lake Michigan, on a private drive. Just South of Sheboygan. Close by: Whistling Straits & PGA golf courses. Ice Age Trail in the Kettle Moraine, Elkhart Lake - Road America, Charter Fishing, Kohler Andrae State Park, Several State & local beaches, & several 5 star restaurants. 2 hours & 20 min from Chicago. 45 min from Milwaukee, 65 min from Green Bay. Rest, Relax and Unwind in the tranquil setting at Sandalwood.

Guest favorite

Home in Elkhart Lake

4.93 out of 5 average rating, 206 reviews

The LODGE in Elkhart Lake

Rustic modern home w/ hot tub, arcade and fireplace right on the edge of Elkhart Lake. Road America, great golf, The Ice Age Trail, and the Kettle Moraine are all at your doorstep. You will be staying in a cute & cozy home 4 blocks from the downtown of Elkhart lake. Yet it still has an acre to explore and enjoy nature. We are also only 4 miles from Road America. 2 bedroom, 2 bathroom. Perfect for racers or romantic getaways. The arcade/Pinball room has over 10 games. We got your bases covered!

Guest favorite

Home in Sheboygan

4.98 out of 5 average rating, 167 reviews

Boutique Wellness Retreat - Hot Tub and Fireplace

Enjoy this beautifully landscaped and decorated boutique home. New patio and deck! Hot tub/Dry Sauna! Comfort and charm throughout. Cooks kitchen with all amenities. Primary bedroom with Stearns and Foster King size bed. The beautiful fireplace in the living room is perfect for a relaxing couples evening. Enjoy a glass of wine or local brew on the patio while you grill out. EV Charger and E-Bikes to explore the area. Sonos audio throughout. This beautiful boutique home is sure to impress!

Guest favorite

Rental unit in Sheboygan

4.98 out of 5 average rating, 130 reviews

Lovely modern two bedroom home with fire pit

Newly renovated two bedroom home just a mile from the beach and five star restaurants. Enjoy a game of golf at world class Whistling Straight. Car enthusiasts will love Elkhart Lake Road America. Salmon fishing the Great Lake Michigan or just have a relaxing time around the fire pit. There is a laundry with washer/dryer, steamer and folding table. Dogs under 30 pounds. No cats sorry. No smoking in the house. Ample street parking at the front door. Fire pit in back yard.

Guest favorite

Home in Oostburg

4.96 out of 5 average rating, 154 reviews

Lake Michigan Beach Home by Frank Lloyd Wright pro

Beautiful view and sand beach on Lake Michigan completely private surrounded by mature white pine trees and cedar trees. The spacious home is fully equipped with an "eat in" kitchen, dining room and living room entertainment space, den with see thru log fired fireplace, screened in porch to accommodate additional eating space, large outdoor deck with grill and fire pit. A canoe and row boat are available for the boating enthusiast, with life jackets and other floating devices.

Guest favorite

Home in Sheboygan

4.94 out of 5 average rating, 189 reviews

Beachfront getaway in Sheboygan

One of the few homes in Sheboygan that walks out onto the sands of Lake Michigan, this 3 bedroom/ 2 bath home is meant for total relaxation and fun. The open kitchen, dining and living room is full of light from the sliding glass doors on the back of the house, which access a deck and a large back yard. Upstairs is a spacious loft with a pull out couch. Fire pit in the back yard. Just steps from a playground at King Park. Amazing sunrises, worth waking up for.

Guest favorite

Home in Oostburg

4.96 out of 5 average rating, 186 reviews

Shamba on the Lake, Oostburg, WI

Large guest home , in a rustic setting, on a peaceful 2-acre wooded lot (only 5 homes on a very private road) on Lake Michigan with a large private beach a few feet from the deck. . Magnificent panoramic view, amazing sunrises, serene twilights, magical star-studded night skies. A slice of Paradise you must experience. Located a mile from I43, 40 minutes from downtown Milwaukee, 20 mins. from golf courses in Kohler, 30 mins. from Road America in Elkhart Lake...

Guest favorite

Home in Sheboygan

4.96 out of 5 average rating, 112 reviews

Good VIBES On the Third COAST- Pets Welcome

Peaceful bohemian retreat with a lively vibe! Perfect for couples, remote workers, girls weekends, golf outings and families! A short walk /bike ride downtown, to the lake or farmer's market. Visit locally owned shops and the world-renowned Kohler Art Museum. Only a 10 minute drive to the famous Whistling Straits/Irish golf course or Kohler Water Spa. Whatever brings you here, we look forward to your visit. Come and enjoy everything Sheboygan has to offer!

Guest favorite

Home in Sheboygan

4.97 out of 5 average rating, 135 reviews

Lake Michigan home with gorgeous views!

Our beautiful lakefront home is perfect for bringing everyone together - Ladies weekend, guys golf trip, family reunion, Packers games...this is your place. Minutes to downtown Sheboygan/Kohler, with 5 star PGA championship golf courses (Black Wolf Run, Whistling Straits, The Bull of Pinehurst), Kohler Waters Spa, and the beaches/dunes of Kohler Andrae State Park. Renovated bedroom and movie room completed early 2020.

Guest favorite

Home in Sheboygan

4.94 out of 5 average rating, 268 reviews

River Home Getaway with River Access - Sleeps 8

Enjoy your getaway in the comfort of the River Home. With the Sheboygan River flowing through your backyard and living spaces stylishly decorated, the scene is set for a truly remarkable vacation. The eat in kitchen is equipped with all the necessities to whip up a delightful meal. The family room has a variety of board games as well as a smart TV for entertainment. The space is complete with four well-appointed bedrooms.