Apartment vacation rentals in Sheboygan

5 out of 5 average rating, 7 reviews

Storybook Home - 1 mi to Lake & Downtown Sheboygan

Welcome to The Fox & Folly Inn 🦊 —a unique whimsical retreat. Perfect for families and those who are kids at heart! 🖼️ Creative and cozy home with art and murals. 🦊🐰🦉Themed with original characters. Audio stories & endless charm! 🛏️ Master Bedroom - King Bed 🛋️ 2nd Bedroom - Bunk Bed = Full Lower, Twin Upper 🛌 Sleeps 5 🛁 1 Full Bathroom - Towels, Hair Dryer+ 🍽️ Fully Stocked Kitchen 🅿️ Off-Street Parking 🏖️Minutes from the beach & Bookworm Gardens 📖Your storybook adventure awaits!

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, 216 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!

An open living space features a round dining table with four chairs, complemented by a cozy seating area with a sofa adorned in warm tones. Natural light filters through large windows, while string lights add a gentle illumination to the ceiling.

4.94 out of 5 average rating, 50 reviews

Parkside Studio Apartment

Escape to this peaceful family retreat next to a wooded park! Just 2 mins. from Lake Michigan, 5 mins. from Kohler-Andrae State Park, and 10 mins. from the harbor, our spacious, newly remodeled studio offers the perfect getaway. It's ideal for families with a king bed, bunk bed, and pullout queen sofa. Enjoy free Wi-Fi, Smart TV, a dedicated workspace, and hassle-free parking. Whether exploring the outdoors or simply unwinding, this cozy haven has all the comforts you need for a memorable stay!

A comfortable living area is presented with a navy blue sofa adorned with decorative pillows. A glass coffee table sits in front of the sofa, reflecting light. A world map artwork is displayed on the wall above, with a kitchen visible in the background.

4.98 out of 5 average rating, 60 reviews

A Wave From It All! - Lake Condo

Welcome to Lake Michigan! Fish, surf, shop or golf, this condo is close to it all. Easy secure entry, ground floor. The boardwalk (South), offers green space, tables, restaurants, scenic water views and walking areas. Head North to almost a mile of beach, playgrounds, tennis courts, lake history and the recovered remains of Great Lakes schooner Lottie Cooper capsized in 1894. We provide accommodations for four, this 2-bedroom 1-bathroom condo has a full kitchen, living room and street parking.

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.

4.9 out of 5 average rating, 113 reviews

The Beach | Sheboygan 2Br/1 Ba

Welcome to the Beach, a lakeside retreat in the heart of Sheboygan. Located just 3 blocks from Lake Michigan and a stones throw to down town Sheboygan, The Beach is the perfect place to center your visit to Eastern Wisconsin. The Beach is the main floor unit of a duplex featuring 2 bedrooms, 1 bathroom, a well stocked kitchen, a cozy living room, fast wifi and convenient amenities. We have an easy check out with no to-do lists. Just pack and go! *New cleaning staff hired January 2023!*

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.

4.98 out of 5 average rating, 186 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, 547 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.

5 out of 5 average rating, 208 reviews

A neatly arranged countertop displays a candle labeled 'Blush Floral' alongside a clear vase filled with fresh red roses. A sleek soap dispenser, marked 'Church Street Hand Soap,' sits prominently, enhancing the serene ambiance of the space.

Apartment in Kohler

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.

5 out of 5 average rating, 6 reviews

Charming Historic Lower Unit King/Queen Sleeps 6

Beautifully restored lower unit with high, detailed ceilings and stylish historic charm. Sleep 6 w/King and Queen-sized bedrooms, and a large sleeper sofa. Spacious and open with a fully stocked kitchen and large dining area! Off-street parking, centrally located 1 mile from the beach, 10-min walk to close-by bars and food spots, or 3 min drive to downtown restaurants, boutique shops, parks. Perfect for relaxing getaways or work-friendly stays!

Apartment in Downtown Sheboygan

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, 245 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.

4.87 out of 5 average rating, 118 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, 291 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

4.63 out of 5 average rating, 342 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.

4.76 out of 5 average rating, 45 reviews

Bed & Beer -4 bdrm above a bar

Superhost

A well-lit living room features two black leather sofas and a futon, providing ample seating. A wooden coffee table sits centrally, with a lamp illuminating the space. Accent chairs complement the arrangement, and natural light enters through partially covered windows.

4.79 out of 5 average rating, 24 reviews

On Broadway

4.71 out of 5 average rating, 66 reviews

Classic Sheboygan

5 out of 5 average rating, 5 reviews

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.

Apartment in North Point

Knot A Care By The Lake

Superhost

A welcoming living area features a dark leather sofa and a recliner, arranged around a coffee table. A modern fireplace with a stone surround adds warmth, while large windows provide natural light. Two framed art pieces enhance the wall, creating a cozy atmosphere.

Modern Nomad - Monthly Rates Available!

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, 79 reviews

Downtown Elkhart Lake - The Quintessential Suite

4.96 out of 5 average rating, 52 reviews

The two-story farmhouse is characterized by its historic brick exterior and large windows. A green lawn surrounds the house, complemented by a colorful sunset in the background. The structure features a porch with railings, providing an inviting outdoor space.

Apartment in Kewaskum

The Cozy Country Farmhouse, Eisenbahn Suite

Private apartment rentals

Apartment in Campbellsport

4.95 out of 5 average rating, 40 reviews

'McJugger’s Loft:' Walk to Lake, Park, Restaurants

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, 63 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.

4.84 out of 5 average rating, 32 reviews

Helene's room

Apartment in Sheboygan Falls

A well-appointed bedroom features a spacious bed dressed in white linens. A quilted blanket is neatly placed at the foot of the bed. A gray patterned rug lies underfoot, complemented by a stylish bench and a light gray accent chair beside a window with light-filtering blinds.

4.9 out of 5 average rating, 10 reviews

Elegant Condo in Sheb Falls

A residential property is shown with a welcoming exterior, surrounded by lush greenery and well-maintained landscaping. A large tree provides shade in the foreground, while a driveway leads to a two-car garage in the background. Soft light filters through the leaves, enhancing the serene atmosphere.

4.67 out of 5 average rating, 9 reviews

Sheboygan Getaway w/ Deck + On-Site Lake Access!

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

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

Family-friendly apartment rentals

A spacious room features two queen beds dressed in light-colored bedding. A wooden dresser and a desk are positioned against the wall, with natural light entering through sliding glass doors leading to a balcony. A ceiling fan adds comfort to the ambiance.

4.62 out of 5 average rating, 21 reviews

Siebkens Lockout Unit

The exterior view of a two-story home is presented, featuring a well-maintained facade with white siding and dark green accents. A spacious driveway accommodates multiple vehicles, while a wooden front porch leads to the entrance. Lush green trees frame the property.

4.88 out of 5 average rating, 16 reviews

Elkhart Lake Flat - 3 Min to Road America

Apartment in Downtown Sheboygan

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.

4.91 out of 5 average rating, 151 reviews

Sheboygan Surf House - North Point

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

Newly updated efficiency - cozy & convenient.

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.

4.82 out of 5 average rating, 11 reviews

3 BR Lower-Brand New Remodel

A charming two-story farm home is framed by lush greenery and well-maintained gardens. A spacious driveway leads to the entrance, showcasing a blend of colorful flowers and neatly trimmed hedges. The home's exterior features subtle blue siding and welcoming accents.

Apartment in Plymouth

Kettle Edge Retreat and Gardens

A two-story white farmhouse is viewed from a distance, set against a clear blue sky. Lush green grass surrounds the property, complemented by a flowering shrub near the entrance. A paved driveway leads up to the home, which features a welcoming front porch.