Apartment vacation rentals in Sheboygan County

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Top-rated apartment rentals in Sheboygan County

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Top guest favorite

An open living space is showcased, featuring a comfortable sectional sofa and a minimalist coffee table. A dining area with two stools is visible next to the kitchenette. Natural light filters through the windows, illuminating the neutral-toned furnishings and wood-style flooring.

Apartment in Sheboygan

4.97 out of 5 average rating, 157 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!

Superhost

The living room features a cozy seating arrangement with two armchairs and a sofa, in front of a wooden coffee table. Natural light enters through two windows adorned with sheer curtains, illuminating the green walls and wooden flooring. A television is positioned on a media console against one wall.

Apartment in Plymouth

4.64 out of 5 average rating, 298 reviews

Pineyard Plymouth Apartment

Enjoy this older upper floor apt. with two single bedrooms with a twin bed in one and a full bed in the other, full bath, kitchen, living room, and off street parking. VCR/DVD player and internet is available. Kitchen is equipped with dishes, pots, pans, stove, and refrigerator. We are five minutes from Road America, fifteen minutes from Sheboygan, and thirty minutes from Fond du Lac. Only three blocks from downtown Plymouth enjoy many shops and eating establishments. Pets are NOT allowed.

Top guest favorite

A cozy living area is complemented by a large brown couch and a wooden coffee table adorned with flowers. Natural light fills the space through multiple windows. The room features hardwood flooring and is connected to a dining area visible through an open doorway.

Apartment in Kohler

5 out of 5 average rating, 117 reviews

The Hemingway on Church - It Tolls For Thee

"Kristine's property has all the charm of a modern day Mayberry" -Michael This 1906 historic home is nestled in the heart of the equally historic "Village of Kohler." Completely remodeled in 2019 adding Kohler spa amenities and modern touches to its original charm. Mixing modern & antique furniture finds like the Hemingway Sideboard (which inspired the literary theme) make this historic hideaway a true Kohler destination. "You cannot get a better location in Kohler than this house!" -Dennis

Top guest favorite

A well-appointed bedroom features a spacious bed with white linens and a textured gray throw. Two decorative lamps provide soft lighting on either side of the bed. Bright windows are framed by patterned curtains, and wall art adds a touch of elegance to the neutral-colored walls.

Apartment in Sheboygan

4.95 out of 5 average rating, 38 reviews

Peaceful apartment close to the lake

Beautiful, newly furnished & updated, 2 Queen bedroom upper apartment with large closets, 1 bath, desk with workspace, stocked kitchen, in unit laundry, private balcony, high speed internet, 2 Smart TVs, keyless private entrance Central downtown location walking distance to restaurants/bars, parks, the beach, festivals, Museums, Arts Centers, Stephanie H. Weill Center & more! 10-15 min. driving distance to Kohler golf courses, The Bull at Pinehurst Golf Course, Road America, Elkhart Lake

Top guest favorite

A well-lit living area features a neutral-colored sofa adorned with a soft throw. A glass coffee table sits on a patterned rug, complemented by a wicker basket. Natural light filters through the window, illuminating the space and the nearby armchair.

Apartment in Sheboygan

4.98 out of 5 average rating, 139 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.

Top guest favorite

A cozy living area is highlighted by a large window that overlooks greenery. A comfortable dark sofa and wooden coffee table are arranged around a patterned rug. A rocking chair and armchair provide additional seating, while potted plants add a touch of nature.

Apartment in Sheboygan

4.93 out of 5 average rating, 483 reviews

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.

Guest favorite

A spacious living area features a comfortable light grey sofa and a blue accent chair, complemented by natural light from large windows. A wooden coffee table with decorative items is placed on a patterned rug, with a dining area visible in the background, showcasing a light wooden table and chairs.

Apartment in Sheboygan

4.9 out of 5 average rating, 20 reviews

Newly Updated! Downtown & Shore

Welcome to Superior Commons by Doorway Travel! This newly renovated and professionally decorated apartment is centrally located, just 4 mins to downtown and 5 mins to the shoreline! Upon entry you are welcomed by a spacious living and dining area. Relax and unwind on new memory foam queen mattresses in all bedrooms! 43" Roku TVs in all bedrooms and 65" Roku TV in living area. Kitchen is fully stocked for meal preparation. Enjoy the coffee & tea bar! We are pet friendly!

Superhost

A cozy seating area is highlighted by a gray love seat adorned with cream pillows. A small glass table sits nearby, with a decorative plant on it. A textured pouf rests on a patterned rug, and natural light filters through the window's blinds.

Apartment in Sheboygan

4.84 out of 5 average rating, 217 reviews

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

Top guest favorite

A cozy living area showcases a flat-screen television mounted above a vintage wooden dresser. An elegant fireplace with detailed woodwork is positioned nearby, complemented by wooden flooring. Decorative items are arranged on the mantel, enhancing the room's charm.

Apartment in Waldo

4.98 out of 5 average rating, 276 reviews

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.

Guest favorite

A modern living area is presented, featuring a comfortable sofa with soft cushions and a stylish coffee table. A decorative area rug adds color to the wood floor. Natural light enters through large windows, while a ceiling fan and warm lighting enhance the space.

Apartment in Sheboygan

5 out of 5 average rating, 7 reviews

Cactus Corner KING Apartment

This stylish, newly remodeled upper unit 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 facing the pretty garden below. The building has a shared laundry area in the basement with two new washers and dryers included for guest use. There is also ample off street parking and a lovely green space.

Guest favorite

A bright living area features a large window allowing natural light to fill the space. Seating includes two chairs with light wood frames and a yellow couch. A small coffee table sits on a textured rug, accompanied by a tall plant adding a touch of greenery.

Apartment in Sheboygan

4.83 out of 5 average rating, 24 reviews

2BR Apt Near Beach & Downtown

Welcome to our charming 2-bed, 1-bath apartment just 2 blocks from the beach and less than a mile from downtown. With a fully equipped kitchen, comfy furnishings, and extra sleeping space for more guests, it's the perfect spot for your city getaway. Start your weekend with a delicious treat from Sunday Dough donut shop downstairs before exploring all that the area has to offer.

Superhost

A modern living area is highlighted by a dark gray sleeper sofa and a round, wooden dining table set for four. Natural light enters through large windows dressed with dark curtains. A potted plant and artwork add a touch of color to the minimalist space.

Apartment in Sheboygan

4.87 out of 5 average rating, 15 reviews

Rock skip from the lake!

Enjoy a stylish experience at this centrally-located place. This one bedroom apartment features furnished kitchen, tiled shower and sleeper sofa. Located in downtown it is surrounded by great dinning and nightlife. Walking distance to the boardwalk and the lake its a perfect little getaway. Close to Golf, Fishing and racing.