Apartment vacation rentals 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!

The Garden | Sheboygan 2 Br/1Ba, Pet Friendly

Welcome to the Garden, a floral retreat in the heart of Sheboygan. Located just 3 blocks from Lake Michigan and a stones throw to down town Sheboygan, The Garden is the perfect place to center your visit to Eastern Wisconsin. The Garden is a pet friendly apartment on the second floor of a duplex with 2 bedrooms, 1 bathroom, a well stocked kitchen, a cozy living room, fast wifi and convenient amenities. Easy check out with no to-do lists. Just pack and go! *new cleaning staff hired Jan’23*

Bird's View King Suite

This upper unit is close to everything, making it easy to plan your visit to Sheboygan. It is fully stocked with everything you need while away from home. Spacious and clean with a dedicated workspace and fast internet. Enjoy some fresh air on the balcony or grill out in the beautiful yard below. The building has a shared laundry area in the basement with two new washers and dryers included for guest use. There is ample off street parking and a lovely green space with picnic table and grill.

Local Landmark CF / Artisan Coffeehouse

Wake up to the aroma of fresh coffee, stroll downstairs for breakfast, then spend the afternoon hiking the Kettle Moraine before returning to a luxurious bed. The iconic Coffee Corner Bistro (Est 1999) is steps from the Wisconsin 9/11 Memorial & Eisenbahn Bike Trail, and is the "Gateway to the Kettle Moraine" Proudly recognized by the Fond du Lac Reporter Travel Section in its June 13, 2026 feature: "Top Airbnb Stays Near Fond du Lac" Google CBS 58 story on our historical Coffeehouse.

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.

The Sheboygan Foodie Flat

Schnazzy upper flat in the heart of Sheboygan’s Eastside. Walk to Lake Michigan Beaches, Riverfront, Uptown and Downtown. Enjoy the newly renovated 2nd floor of an 1893 historic rambler, with lots of natural light. -Desirable Eastside, with walkable neighborhoods. -Large Italian tile walk-in shower with Kohler fixtures. -Fully equipped kitchenette with microwave, convection oven, two-burner hot plate, Keurig, coffee pot & toaster. -New furnishings -Sheboygan Foodie Guidebook

Cozy Sheboygan Upper

We began caring for this home and property in 2018, and this 1870's home needed some love. We have been steadily remodeling since we moved in and it's starting to feel pretty great. We're excited to share it and the neighborhood with you. We are two blocks west of North Beach/Deland Park, 4 blocks to the river front boardwalk, home to many restaurants, cafe's, and shops. We are also four quick blocks to downtown which hosts many more restaurants, shops, museums and parks.

Church Street Romance & Retreats-Village of Kohler

“A well-appointed, cozy and stylish retreat close to everything in Kohler.” -Kim Take the stairs to my secluded 2nd floor tree view retreat! A private side entrance and open floor plan flanked by two bedrooms makes this unit perfect for couples or a girl's getaway spa weekend. Romantic turn-of-the-century touches meet modern convenience & comfort. Baker furniture, previously a Kohler Company, can be found throughout the apartment enhancing your Village of Kohler stay.

Recombobulation Station-In The Heart of Sheboygan!

Experience the charm of this beautifully preserved home while enjoying your private completely renovated 2nd-floor unit. Perfectly nestled in the walkable Ellis Historic District We are local owners who love sharing our town • Blocks from North Beach+Riverwalk+8th St • Record Player+curated vinyl • Stocked Kitchen+Luxurious pillow-top main bed •5 min:Weill Center+Arts Center •15 min:Kohler Spa+Whistling Straits •20 min:Road America •1 hr:Lambeau Field

Sheboygan Surf House - Jetties

Located just 24 steps above Wisconsin's first Surf Shop, EOS Surf. Our Urban living oasis is a fully equipped studio apartment conveniently located in the heart of downtown, just steps from bars and restaurants and only blocks to Lake Michigan South Pier and Blue Harbor. Whether you are here for adventure sports like Surfing on the Great Lake, Kite boarding, charter fishing, a Wedding or leisure time SSH is perfect for you. Support Dog friendly

One Bdrm Apt - The Erie House near lake & downtown

This house was built in 1888 as a single family home and retains its nineteenth century charm along with today's modern conveniences. The location is just walking distance from both majestic Lake Michigan to the east and Sheboygan's charming downtown to the west. The lodging, which sits in an attractive, tree lined neighborhood, has been divided into several living units in which you will be staying on the first floor facing Erie Avenue.

The Blue Cobb House

My place is close to 20 minutes south of Elkhart Lake and Road America. You’ll love my place because of the outdoors space, the comfy bed, and the kitchen. My place is good for couples, solo adventurers, and business travelers. The Blue Cobb House is about 15 minutes from Kohler-Andrae State Park and 30 minutes from Harrington Beach State Park. The Kettle Moraine area is just to our west and it is filled with hiking trails.