Vacation rentals with beach access in Sheboygan

4.91 out of 5 average rating, 386 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.

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, 212 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!

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, 136 reviews

Lakefront Charmer, cheerful decor gorgeous garden

This 2600 sqft lakefront home is a spacious retreat year round, friendly to kids and dogs. It is perched upon a bluff overlooking Lake Michigan with a gorgeous sunrise view. In winter, enjoy passing cargo ships and eagles along with ice formations. Inside, dine with seating and service for 12 after cooking in the spacious kitchen with wood fireplace. Kitchen, living room, dining room and 2 bedrooms have full lake view. 2 large screen tvs. Spa quality bath with whirlpool. Gas fireplace too!

4.96 out of 5 average rating, 312 reviews

The cottage is surrounded by trees, featuring a well-maintained exterior with a shingled roof and a welcoming front path. Colorful flowers and greenery adorn the entrance, while large windows allow for ample natural light. A cozy sitting area is visible near the front door.

Cottage in Oostburg

Sandalwood Cottage - 300 Feet From Lake Michigan

A HIDEAWAY one mile East of I-43 nestled in beautiful wooded acreage across from Lake Michigan, on a private drive. Just South of Sheboygan. Close by: Whistling Straits & PGA golf courses. Ice Age Trail in the Kettle Moraine, Elkhart Lake - Road America, Charter Fishing, Kohler Andrae State Park, Several State & local beaches, & several 5 star restaurants. 2 hours & 20 min from Chicago. 45 min from Milwaukee, 65 min from Green Bay. Rest, Relax and Unwind in the tranquil setting at Sandalwood.

A sunlit corner nook displays a wooden bench adorned with plush, colorful pillows in varying textures. A small circular table holds a potted plant, while a larger leafy plant is positioned nearby. Sheer curtains allow soft light to filter into the space.

4.92 out of 5 average rating, 102 reviews

Coastal Comfort Near Lake MI & Downtown

Welcome to the Coastal Comfort! Comfort: noun - a state of physical ease and freedom from pain or constraint Come in and unwind at our coastal 3 bedroom lower unit home near Downtown Sheboygan, Lake Michigan, Whistling Straits and Kohler/Andrae State Park. You can enjoy an evening at home with all your favorite streaming services, or head out to discover some of Sheboygan’s many hidden gems. If this unit is booked for your dates, send me a message to ask about our other available listings.

A spacious hot tub is filled with bubbling water, inviting relaxation. Surrounding greenery enhances the outdoor setting, while sunlight reflects off the surface of the water. The tub is located under a wooden pergola, providing a cozy space for enjoyment.

4.97 out of 5 average rating, 176 reviews

Lakeview Beach Bungalow - With outdoor Hot Tub!

Enjoy the Holidays at this Beautifully updated beach house just one block off of Lake Michigan. Enjoy the newly landscaped backyard with pergola & 6 person Hot Tub! Watch the sunrise $ sunset from the second floor master balcony. Walk to the lake across the street and enjoy the wind surfers and beach. Close to downtown and parks. This three bedroom home will impress. Tastefully decorated. Large bathroom w/deep soaking tub. For treasure hunters, a Metal detector for family fun at the beach. .

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, 112 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!*

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, 218 reviews

Dog Friendly Cozy Cottage Rental on Lake Michigan!

Kohler Design Center Rentals, Kohler Andrae State Park Rentals, Whistling Straits Rentals, Blue Harbor Rentals, Road America Rentals, Kohler Art Center Rentals, Black Wolf Run Rentals, Lake Michigan Fishing Charters Rentals, Green Bay Packer Rentals, Door County Rentals, Honeymoon Rentals, Women's Weekend Rentals, Lake Michigan Sunrise Rentals, Dog Friendly Rentals, Winter Rentals. Dog Friendly Rentals, Sheboygan, Wisconsin Rentals, Saugatuck, Michigan Rentals, New Buffalo, Michigan Rentals

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, 115 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, 543 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 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, 210 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, 502 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 accommodations

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with beach access

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.

4.84 out of 5 average rating, 96 reviews

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

A contemporary living area features a brown leather couch paired with green and gray cushions. A circular mirror is set above a wooden coffee table adorned with a small potted plant. The space includes hanging greenery and a soft area rug, enhancing a calm ambiance.

4.95 out of 5 average rating, 55 reviews

Sleeps 7{SPACIOUS}Pets Welcome!

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, 88 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, 14 reviews

Overlook Oasis | Coastal Haven in Ellis District

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 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.

4.85 out of 5 average rating, 62 reviews

*NEW* Beautiful & Convenient!

Apartment in Campbellsport

A dining area is showcased, featuring a wooden table set with two plates. A vase with flowers sits at the center. Large windows frame the view of verdant trees, allowing natural light to fill the space.

4.97 out of 5 average rating, 104 reviews

GGG Spacious Log Cabin apartment on the IAT

House rentals with beach access

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, 15 reviews

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

5 out of 5 average rating, 23 reviews

Home in Oostburg

Winter's a good time to stay in&cuddle at Surfdaze

5 out of 5 average rating, 20 reviews

The exterior of a modern two-story house is showcased, featuring a striking white facade with black trim. A covered porch is visible, with teal chairs placed on the inviting deck. Well-maintained landscaping includes small shrubs and a paved walkway leading to the entrance.

Home in North Point

Luxury 4B-2Ba Lake & Beach House

5 out of 5 average rating, 8 reviews

New King Park Beach Lookout Deluxe!

4.96 out of 5 average rating, 206 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

4.96 out of 5 average rating, 47 reviews

The exterior of the home features a charming two-story design with a gabled roof and a welcoming front entrance. Large windows allow natural light to fill the space. A small seating area is visible on the front patio, complemented by greenery and a neatly landscaped yard.

Home in Ellis Historic

The perfect location!

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!

Condo in Sheboygan

New place to stay

Beachfront Condo - Walk to Beach, Sunrise views

Condo in Campbellsport

Lakefront Condo w/ Beach Access in Campbellsport!

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.

4.57 out of 5 average rating, 21 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, 49 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.

4.95 out of 5 average rating, 37 reviews

Heavenly Condo in the Malibu of the Midwest

4.95 out of 5 average rating, 60 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.