Vacation rentals with beach access in Sheboygan

4.91 out of 5 average rating, 377 reviews

A serene lakeshore scene is captured at sunset, with the sun dipping below the horizon, casting warm hues across the sky. Gentle waves are visible in the foreground, while smooth stones line the water's edge.

Guesthouse in Oostburg

Beach House

This guesthouse is detached from the main house, comes with garage parking and has all the amenities you need including a wood-burning fire place! Towels, bath tissue, soaps & travel items. AC Window Unit. Kitchen includes pots/pans, dishes, mugs/glasses, coffee pot, toaster & microwave. Paper goods. New appliances/new water heater in 2020. Stairs to the apartment are on the northeast corner of the garage. The beach is steps away with a fire pit, boat house lounge, kayaks, beach toys & bicycles.

4.99 out of 5 average rating, 156 reviews

Castle in Cleveland

Castle Vineyard | Luxe Spa • Golf Sim • Theater

Stay at one of the most Wishlisted Airbnbs in the world. Featured in Men’s Health and on the cover of Haven magazine, The Castle Vineyard is a world-class destination 🍇 20-acre estate w/ vineyard, spa, & sauna 🎬 Private theater, arcade, PS5 & golf simulator 🍽️ Chef’s kitchen w/ Viking appliances 🔥 Fire pit, patio, hot tub, wildlife views 🏰 "Felt like royalty... every detail was magical" 🎉 Entire property is yours — guests may inquire about our exclusive Tasting Room for special events

A modern kitchen features sleek white cabinetry and stainless steel appliances, including a large refrigerator and a gas range. Light granite countertops provide ample workspace, complemented by warm lighting from a stylish overhead fixture. The space is accentuated by a neutral-colored door leading to the entrance.

4.98 out of 5 average rating, 124 reviews

Modern Lower Apt - One block to the Lake

Part 1 of 2 Amazing AirBnB apartments in this ideally located duplex. *Disclaimer - this apartment offers a true lower level living experience. You may notice some noise, including foot traffic, from your amazing upstairs Airbnb neighbors. But.. with all the great restaurants, golf, fishing, and the beach nearby you won’t even have the time to hear it! Located only 1 block from the beach on Lake Michigan - you’ll find relaxation and a great time here at the heart of Sheboygan’s Shoreline.

4.9 out of 5 average rating, 109 reviews

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.

Apartment in Sheboygan

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!*

The kitchen area offers light wood cabinetry and a breakfast bar, with a dining table that seats four. Large sliding glass doors provide views of the lake, while ample counter space accompanies a full-size refrigerator and modern appliances.

4.86 out of 5 average rating, 216 reviews

Dog Friendly Cozy Cottage Rental on Lake Michigan!

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4.95 out of 5 average rating, 154 reviews

A modern single-story home features a light gray exterior with a striking yellow front door. Large windows provide abundant natural light, while a well-maintained lawn is complemented by colorful flower beds. Skylights on the roof enhance the home's contemporary design.

Home in Cleveland

Modern Home Just 40 Minutes from GB NFL Draft

My home is just minutes from Whistling Straits Golf, Road America, Lake Michigan, Parks, Hiking, Biking, Snowshoeing, and Cross Country Skiing. You’ll love my place as it's newly remodeled, modern & cozy. The kitchen and living areas have high ceilings, sky lights & new furniture. The large outdoor living area is perfect for social time. My favorite is the heated bathroom floors. My place is perfect for golfers, wedding groups, couples, business travelers, and families (with kids & dogs).

4.96 out of 5 average rating, 168 reviews

An aerial view of a spacious home is surrounded by mature trees, showcasing a private sandy beach alongside Lake Michigan. The property features a pathway leading to the house, emphasizing its secluded setting amid natural greenery.

Home in Oostburg

Lake Michigan Beach Home by Frank Lloyd Wright pro

Beautiful view and sand beach on Lake Michigan, completely private, surrounded by mature white pine trees and cedar trees. The spacious home is fully equipped with an "eat in" kitchen, dining room, and living room entertainment space, den with a see-through log-fired fireplace, screened-in porch to accommodate additional eating space, large outdoor deck with grill and fire pit. A canoe and a row boat are available for the boating enthusiast, with life jackets and other floating devices.

Loft in Downtown Sheboygan

A spacious living area features a dark leather sectional sofa with colorful throw pillows. A textured ottoman sits in front, while natural light streams through large windows, illuminating the warm brick wall and wooden furniture. A decorative coffee table holds books and a candle.

4.97 out of 5 average rating, 111 reviews

Spacious/stylish, 2br loft

Lots of space in active downtown Sheboygan. Full kitchen w/essentials, washer/dryer, 1.5 baths, 2 queen, 2 twin ready for family/friends. Stocked w/home essentials. 3 Smart TVs, free WIFI. Pay-as-you-go parking lot in rear but free nights/weekends. Wonderful walkable neighborhood near shops, restaurants, art & children’s museum, river walk & lake front (a bit further). Short drive to Kohler, Whistling Straits golf course, Shops at Woodlake & Kohler Design Center. Marcus cinema near by.

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, 531 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.

4.88 out of 5 average rating, 211 reviews

A view from the open door showcases a spacious deck leading to a grassy area with trees. Beyond the greenery, the blue waters of Lake Michigan are visible, capturing a serene outdoor scene.

Condo in Sheboygan

Beachside Lake View - 2br - First Floor - Garage

Located just one lot in from the beautiful shores or Lake Michigan. Amazing location provides year round stunning views . This is a lower 2 bedroom 1 bath condo in a 4unit building were all the units have the same basic layout. You can listen to the waves or walk just a few feet and have the sand on your feet. This condo features front and rear balconies. Makes for a great place to enjoy a weekend get away or a place to relax at night while on a business trip.

A tranquil view of Lake Michigan at sunset, where calm waters reflect soft hues of orange and pink. The sky showcases wispy clouds, and a distant bird is seen soaring above the serene landscape, creating a peaceful setting.

4.94 out of 5 average rating, 206 reviews

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.

Superhost

A view of the serene shoreline along Lake Michigan is presented, framed by lush greenery. A blue railing leads down toward the beach, where sand and water are visible, inviting outdoor activities. The sky is overcast, creating a calm atmosphere.

Guesthouse in North Point

4.82 out of 5 average rating, 490 reviews

Carriage House Sheboygan, Lake Mich beach access!

The Carriage House is the perfect getaway. Located in a beautiful historic neighborhood with Lake Michigan public beach access across the street, 100 yards away. Ideal for a family of four or an individual in town for business. Amenities have been thoughtfully placed to create the most comfortable and convenient stay for guests. We pride ourselves on ensuring you enjoy your stay with us and guarantee you'll love the neighborhood!

Popular amenities for Sheboygan beach access rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with beach access

A serene bedroom features a queen-size bed with light-colored bedding, complemented by a plush rug. Natural light fills the room through three windows, creating a bright atmosphere. A patterned chair and a tall black storage unit complete the space, showcasing hardwood flooring throughout.

4.79 out of 5 average rating, 43 reviews

Prime central location-Tempurpedic

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, 85 reviews

Recombobulation Station-Locally Owned Surf Escape

A comfortable living area features a gray sofa adorned with patterned cushions. A small dark table sits in front, accompanied by a throw blanket draped casually. Natural light is filtered through sheer and dark curtains framing two windows.

4.91 out of 5 average rating, 22 reviews

Home away from home

A charming two-story building is shown, featuring light-colored siding and a welcoming front porch. A well-maintained lawn and a gravel seating area with simple outdoor furniture are visible, enhancing the inviting atmosphere of the property.

5 out of 5 average rating, 12 reviews

Overlook Oasis | Coastal Haven in Ellis District

Apartment in Elkhart Lake

A red vintage sports car is parked on the driveway beside a two-story building. Tall trees frame the area, and a sunset casts a warm glow in the background, enhancing the serene country setting.

4.93 out of 5 average rating, 155 reviews

Schoolhouse Straight Inn

Apartment in Elkhart Lake

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 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, 202 reviews

Modern Upstairs Apt - Steps from Lake Michigan

4.85 out of 5 average rating, 60 reviews

A light-filled living space is furnished with a comfortable blue sofa and armchair. A round coffee table sits atop a soft area rug, while a large TV is positioned on a wooden media console. Natural light filters through the window, complemented by a potted plant.

Apartment in Sheboygan

*NEW* Beautiful & Convenient!

House rentals with beach access

The Victorian home showcases a charming, multi-level façade with intricate details and a light-colored exterior. Welcoming porches are present at the front, surrounded by well-maintained landscaping featuring green grass and vibrant flowers, all under a clear blue sky.

5 out of 5 average rating, 81 reviews

Updated Victorian in the Heart of Sheboygan

5 out of 5 average rating, 11 reviews

Home in North Point

A Cozy Lake Break

5 out of 5 average rating, 56 reviews

Home in Ellis Historic

Art Collector's Dream - Remodeled w/ Gallery Vibes

A serene beach stretches along the shoreline, with gentle waves lapping at the sandy coast. The sky is painted with soft pastel hues as the sun sets, casting a warm glow over the water. A few trees line the beach in the distance.

5 out of 5 average rating, 14 reviews

Clara Vida Inn- 1/2 Block from Lake and beach!

5 out of 5 average rating, 31 reviews

The spacious living area showcases a modern design, featuring a wooden accent wall and cozy seating arrangements. Large windows are adorned with cheerful yellow curtains, allowing natural light to brighten the room. Colorful artwork adds visual interest, complemented by a contemporary fireplace.

Home in Ellis Historic

Beachside, Chefs Kitchen, High-End Everything

A spacious living area is featured with a comfortable blue couch and a coffee table positioned on a decorative rug. Natural light is welcomed through large windows, while framed artwork adorns the walls. An adjoining dining area is visible through elegant wooden archways.

4.96 out of 5 average rating, 137 reviews

Four Bedroom Family Getaway Home In Sheboygan

The kitchen features a spacious granite countertop and a black sink, highlighted by wooden cabinetry. A large window allows natural light to fill the room, showcasing scenic outdoor views. Colorful yellow chairs and a small table create a cozy seating area nearby.

4.97 out of 5 average rating, 135 reviews

Lakefront Charmer, cheerful decor gorgeous garden

4.96 out of 5 average rating, 205 reviews

A spacious guest home is set against a backdrop of tall trees, positioned near a sandy beach. The exterior features a covered porch and two lounge chairs, inviting relaxation while enjoying the serene landscape.

Home in Oostburg

Shamba on the Lake, Oostburg, WI

Condo rentals with beach access

An outdoor balcony features a wooden table with colorful place settings and a small planter. Comfortable seating is provided by woven chairs and a red cushioned chair. A decorative privacy screen and clear blue skies create a warm and inviting outdoor space.

5 out of 5 average rating, 6 reviews

Welcome to our Cozy Lake Condo!

The exterior of a charming building is presented, featuring a distinctive red roof and white siding. A reserved parking space is visible in the foreground, along with colorful flowerbeds that add a vibrant touch. The entrance is framed by a spacious porch, leading to the main entrance.

Condo in Campbellsport

5 out of 5 average rating, 4 reviews

2BR Condo on a resort on the lake w/beach access

The exterior of a two-story building features a classic design with a light blue facade and white trim. Two spacious balconies with white railings overlook a well-maintained lawn. Stone chimneys are visible on either side, set against a clear blue sky.

4.58 out of 5 average rating, 19 reviews

Edgewater Escape: 4 Bedroom, Sleeps 14!

The exterior of a charming two-story building is shown, featuring white siding and red roofs. Stone pillars flank the entrance, and a spacious porch is visible on the lower level. Well-manicured grass and landscaped areas surround the structure.

4.98 out of 5 average rating, 48 reviews

A Glorious Getaway Sheboygan - LUX Lake Condo

A spacious living area is highlighted by large glass sliding doors that offer views of a green landscape. A comfortable sectional sofa is adorned with colorful cushions, complemented by a round coffee table on a patterned rug. A vibrant piece of wall art adds a touch of charm.

4.94 out of 5 average rating, 36 reviews

Heavenly Condo in the Malibu of the Midwest

4.95 out of 5 average rating, 56 reviews

A well-lit bedroom features a queen-size bed with a patterned blue and white duvet, complemented by neatly arranged towels. A nightstand with a bedside lamp stands beside the bed, and natural light enters through a window dressed with blue curtains.

Condo in Ellis Historic

Ellis District Urban Lake Condo

A serene view from the second-story balcony overlooks the sandy beach and expansive lake. Soft waves lap at the shore under a cloudy sky, with a faint rainbow visible in the distance, creating a tranquil atmosphere for relaxation.

4.95 out of 5 average rating, 61 reviews

Beach condo for 12: 4 bdrms, 2+ baths, treadmill

The exterior of the Crystal Cove condo features a charming white façade with detailed trim and a welcoming front porch adorned with elegant railings. Lush flowering bushes and manicured landscaping enhance the entrance, inviting guests to enjoy the lakeside community.