Holiday rentals with outdoor seating in Sheboygan

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!

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.

Relaxing Sheboygan/Kohler Getaway

Newly remodeled townhouse with all the comforts to make you feel at home in quiet neighborhood, boasting a spacious backyard w/patio, fire pit & free parking. Amenities include well-equipped kitchen, 2 BR & 2 BA, washer/dryer, wi-fi, & smart TV. Conveniently located within minutes to Village of Kohler, Downtown Sheboygan & Lakefront, Black Wolf Run, Whistling Straits (14 min), Road America (18 min), Kohler-Andrae State Park (16 min), grocery stores, restaurants, shopping & local entertainment.

House Near the Lake

Get out and enjoy nature, then return to a quiet mix of modern and retro in this family home only a block away from Lake Michigan. There are three parks and two beaches within a mile, as well as Terry Andrae State Park about 10 minutes away. If the outdoors aren't your thing, downtown Sheboygan hosts the Kohler Art Center, The Weil Center, Blue Harbor, and the Children's Museum, with Road America only 30 minutes away. Located between Milwaukee and Green Bay, this home has all the conveniences.

Boutique Wellness Retreat - Hot Tub and Fireplace

Celebrate your special occasion in Sheboygan at this beautiful boutique home. New patio and deck! Hot tub/Dry Sauna! Comfort and charm throughout. Cooks kitchen with all amenities. Primary bedroom w/King size bed. Secondary bedroom has 2 twin beds. 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. Let us impress you and help make it a memory.

Quiet Country Charm

Cozy barn loft with rustic charm. This newly renovated private loft sleeps 4 with the possibility of 1 or 2 more if you don’t mind sleeping on an air mattress. This room includes a bathroom with shower and small efficiency kitchen with microwave, coffee maker, and small refrigerator. The futon pulls out to a double bed. This relaxing local comes complete with barnyard animals for an authentic Wisconsin experience! You won’t forget the peaceful surroundings of this rustic destination.

LUX Downtown Escape | Outdoor Movie Screen

Welcome to our beautiful 2-bedroom historic home in Downtown Sheboygan! This charming and well-appointed residence offers a comfortable and stylish stay for your visit to the area. From the Chef’s kitchen, comfortable living room, and peaceful backyard, to its prime location within walking distance of Sheboygan's vibrant nightlife, theater, and restaurants, you'll have everything you need right at your doorstep. The home is also just a few blocks from Lake Michigan's beautiful beaches.

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.

Logan's Guest Nest

Logan's Guest Nest is located in a nice small town feel area. With a small look on the outside your Nest has a big feel on the inside. Spacious rooms and quiet area to rest after a day at the many beaches lining Lake Michigan. Or coming back from the races at Road America. Not to mention a day of golf at the many area courses, Whistling Straits maybe. All these wonderful outings are just minutes from the Nest. Plenty of local dinning or delivery for a nice ending of the day.

King Bed Near Lake w/ Fire Pit & Pack N Play

Welcome to the Getaway! Getaway: noun - an act or instance of getting away; a place suitable for a vacation You will unwind in this peaceful 3 bedroom lower unit near Lake Michigan, Whistling Straits and Kohler/Andrae State Park. You can enjoy an evening around the fire pit, or if you don’t feel like staying in, head out to discover some of Sheboygan’s many hidden gems. If this unit is booked for your dates, send me a message to ask about our other available listings.

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.

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!