Apartment vacation rentals in Sheboygan

A cozy living room is presented with floral wallpaper and natural light from a large window. Soft couches adorned with decorative pillows are complemented by armchairs. A dark wood coffee table occupies the center, while a floor lamp and side table add functionality and warmth.

4.85 out of 5 average rating, 101 reviews

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*

A well-lit bedroom features a spacious bed with a dark headboard and light bedding. Two bedside lamps illuminate the room, complemented by natural light from the two windows. A wall-mounted television adds functionality, while a piece of art decorates one wall, enhancing the inviting ambiance.

4.98 out of 5 average rating, 248 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!

4.97 out of 5 average rating, 154 reviews

A wooden table displays a variety of items: an open book, a lime, a glass filled with dark liquid, and a bottle of rum beside a vintage Coca-Cola. A bouquet of vibrant flowers sits neatly in the background, with light filtering through a window.

Apartment in Kohler

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

4.98 out of 5 average rating, 107 reviews

A two-story brick building houses a coffee shop on the ground floor, featuring large windows flanked by a striped awning. The entrance is highlighted by a sign that announces it as Kettle Moraine's Favorite Espresso Bar. A welcoming atmosphere is created by its corner placement and outdoor seating area.

Apartment in Kewaskum

Local Landmark CF / Coffeehouse / Kettle Moraine

One-of-three suites located above a local landmark. The iconic Coffee Corner Bistro (est 1999), is steps from the Wisconsin 9/11 Memorial & Eisenbahn Bike Trail, and is considered the "Gateway to the Kettle Moraine". West Bend - 5 minutes, Foundry 45 - 3 minutes, Lomira - 15 minutes. Enjoy relaxing in this spacious, stylish upper flat in a beautiful turn-of-the-century building. Google... “Kewaskum somewhere I just feel at home” and check out CBS 58 story on our historic Coffeehouse

5 out of 5 average rating, 20 reviews

Historic Lower Unit Near Downtown, King/Queen Beds

Beautifully restored lower unit with high, detailed ceilings and stylish historic charm. Sleeps 6 adults w/King and Queen bedrooms, and a large sleeper sofa. Spacious and open with a fully stocked kitchen and gorgeous dining area! Both on and off-street free parking is available. Waterfront parks, bars and food spots, and downtown restaurants & boutique shops are all just a few minutes away. Perfect for relaxing getaways or work-friendly stays! Stay cool with our Central AC

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.

4.99 out of 5 average rating, 200 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.

A comfortable living area features a sectional sofa in a soft grey hue, a rustic wooden coffee table, and natural light streaming through large windows. Unique décor includes a vintage style chair and a wall-mounted shelf with plants and books.

4.93 out of 5 average rating, 573 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.

A comfortable living area features a plush sofa, a bean bag chair, and a modern television. A wooden dining table with three high stools is positioned in the center. Natural light flows in through large windows, enhancing the inviting space.

5 out of 5 average rating, 97 reviews

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

5 out of 5 average rating, 43 reviews

Clean, Comfy Stay Near Parks, Downtown & Lake!

Enjoy a peaceful stay near Sheboygan’s lakefront, family parks, and downtown eats. This clean, cozy 2BR unit offers everything you need—walkable location, garage parking, full kitchen, and thoughtful touches like old-school Nintendo and local recommendations. ⭐ “Clean, comfy, quiet—close to everything. We’ll definitely stay again!” – Roger ✓ Minutes to downtown & Lake Michigan ✓ Family park across the street ✓ Garage + easy onsite parking

A compact kitchen area showcases modern cabinetry and essential appliances, including a refrigerator and a stove. A small counter with two stools provides a space for dining or working, accented by natural light filtering through a window. Decorative elements enhance the inviting atmosphere.

4.84 out of 5 average rating, 247 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

A spacious living room is equipped with a comfortable sofa and two armchairs. A TV screen is positioned adjacent to an original fireplace, which now houses an electric device. Natural light enters through a window, and a decorative area rug enhances the room's charm.

4.88 out of 5 average rating, 127 reviews

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.

4.98 out of 5 average rating, 305 reviews

A quaint living space features an antique-style fireplace made of dark wood, with a circular mirror above it. A flat-screen television is mounted on the wall opposite a small table and a suitcase rests on the hardwood floor, accompanied by a decorative flower arrangement.

Apartment in Waldo

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.

Popular amenities for Sheboygan apartment rentals

Kitchen

Wifi

Free parking on premises

Air conditioning

Weekly apartment rentals

A simple entrance is highlighted by a white door adorned with a small window, framed by green siding. A festive decoration, resembling a snowman, composed of evergreen branches and a golden hat, is positioned beside the door, adding a cheerful touch.

Apartment in Plymouth

4.64 out of 5 average rating, 355 reviews

Pineyard Plymouth Apartment

Superhost

A living room featuring a dark leather sofa, a cozy armchair, and a coffee table on a patterned rug. Natural light filters through double doors leading to a balcony, while two lamps provide additional lighting. Various framed pictures adorn the walls.

4.77 out of 5 average rating, 48 reviews

Bed & Beer -4 bdrm above a bar

5 out of 5 average rating, 4 reviews

Newly updated efficiency - cozy & convenient.

A decorative wooden sign displays the phrase 'Knot A Care by the Lake' in bold black letters. The sign features a braided rope design at the center, enhancing the nautical theme. The background is a light-colored wood, providing a contrasting framework for the text.

5 out of 5 average rating, 5 reviews

Knot A Care By The Lake

4.67 out of 5 average rating, 3 reviews

Comfortable, quiet, and safe. Close to everything.

Superhost

A cozy studio apartment features a full-size bed adjacent to a comfortable couch, accompanied by a coffee table. A smart TV positioned on a white dresser complements the warm wooden accents. The kitchenette is visible, equipped with a stove, sink, and refrigerator. A bathroom area includes a combination tub and shower.

5 out of 5 average rating, 4 reviews

Studio 920 #1- Monthly Rentals!

The modern kitchen showcases rich wooden cabinetry and a large island with granite countertops. A dining table is conveniently set for four, and eight chairs are positioned at the island. Warm lighting from pendant fixtures creates an inviting space, complemented by natural wood flooring.

4.99 out of 5 average rating, 80 reviews

Downtown Elkhart Lake - The Quintessential Suite

A spacious living room with large windows offers abundant natural light and views of the river and Lake Michigan. Two comfortable couches and a coffee table are arranged around a media console with a television. A ceiling fan provides circulation, and decor includes nautical accents.

4.65 out of 5 average rating, 23 reviews

Welcome to Harbor Nights!

Private apartment rentals

The exterior of a two-story residence is visible, featuring a well-kept front yard with a variety of flowering plants and shrubs. A concrete pathway leads to a set of stairs, which ascend to the entrance. Tall trees provide shade, enhancing the greenery surrounding the home.

4.92 out of 5 average rating, 12 reviews

Logan Ave Holiday House - Upper

The exterior of a renovated farmhouse is displayed, showcasing light grey siding and a wooden deck adorned with potted plants. Ample greenery surrounds the property, and multiple windows reflect the surrounding natural light. A cozy seating area is visible on the deck, inviting relaxation.

5 out of 5 average rating, 64 reviews

Lime Ridge Guest House

A cozy room features an original brick wall, a queen-size sleep number bed, and a small dining area with a wooden table and chairs. A double whirlpool tub is positioned nearby, with a private bathroom visible. A flat-screen TV is mounted on the wall.

4.85 out of 5 average rating, 33 reviews

Helene's room

A comfortable living area features a light-colored sofa and armchair, with a wooden coffee table at the center. A flat-screen TV is situated on a stand, while a lamp illuminates the corner. Natural light enters through the windows, enhancing the cozy ambiance.

4.9 out of 5 average rating, 29 reviews

Cozy Unit w/ Patio: Walk to Dining, Lake Elkhart!

4.71 out of 5 average rating, 66 reviews

Classic Sheboygan

A warm living area features two leather sofas and a wooden coffee table atop a patterned area rug. A dining table with four chairs sits nearby, illuminated by natural light from the windows dressed with light curtains. Framed art pieces adorn the walls.

4.92 out of 5 average rating, 26 reviews

Lovely Elkhart Lake Apartment - Walk to Town!

Apartment in Sheboygan Falls

A living area is showcased with a flat-screen TV mounted on a stand and a round dining table surrounded by wooden chairs. A cozy bedroom is visible in the background, and large windows allow natural light to illuminate the space.

4.94 out of 5 average rating, 18 reviews

Country Apartment

4.88 out of 5 average rating, 52 reviews

A charming farmhouse with a light exterior is presented alongside a contrasting red barn. Well-maintained lawns and vibrant green plantings frame the property, while a paved driveway leads to the home's entrance under a clear blue sky.

Apartment in Kewaskum

Studio near Kettle Moraine Forest-hikers paradise!

Family-friendly apartment rentals

Apartment in West Bend

New place to stay

Barton 1886

A leather sectional sofa is positioned beside a round coffee table, set on a textured area rug. A vintage surfboard is displayed above the couch, complementing the decor. A chair and lamp provide additional seating, while a small dresser holds a decorative lamp, enhancing the cozy ambiance.

4.92 out of 5 average rating, 153 reviews

Sheboygan Surf House - North Point

5 out of 5 average rating, 9 reviews

A comfortable living area features a green sectional sofa and two round coffee tables. A lamp illuminates the space, complemented by a dining table against the wall. Large sliding doors lead to a balcony with views of greenery, creating a serene atmosphere.

Apartment in West Bend

2 Bed/1 Bath Condo - West Bend

A cozy living room is furnished with two patterned sofas and an armchair, arranged around a glass coffee table. Natural light filters through large windows adorned with blinds, illuminating the wooden floor and a decorative rug. A television is positioned near the entrance.

North side Sheboygan, great area

A living room featuring large windows that provide views of the surrounding landscape. A patterned armchair invites relaxation alongside a small side table. A white fireplace serves as a focal point, with a stylish arrangement of decorative items above it. A soft area rug covers the hardwood floor.

5 out of 5 average rating, 11 reviews

Resort Condo on Elkhart Lake

A modern kitchen features sleek white cabinetry and a marble backsplash. Stainless steel appliances include a dishwasher and a gas range, complemented by a wooden range hood. A decorative area rug lies on the light wood flooring, enriching the overall design.

3 BR Lower-Brand New Remodel

New place to stay

Malibu of the Midwest - Condo near Lake Michigan!

A cozy living room is featured, with a dark sofa, light-colored chairs, and a round pouf. A woven pendant light hangs above, illuminating textured wall art. Natural light filters through multiple windows, highlighting a striped area rug laid on the wooden floor.