Holiday rentals with beach access in Sheboygan County

Find and book unique accommodation with beach access on Airbnb

Top-rated Accommodation with Beach Access in Sheboygan County

Guests agree: These holiday homes with beach access are highly rated for location, cleanliness and more.

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Top Guest favourite

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

4.91 out of 5 average rating, 389 reviews

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.

Guest favourite

A serene view features the sun setting over a calm lake, reflecting warm tones on the water. Silhouettes of ducks can be seen peacefully swimming, while distant trees line the shoreline, creating a tranquil atmosphere.

Cabin in Random Lake

4.94 out of 5 average rating, 109 reviews

The Random Cabin (On Random Lake)

Suprising Waterfront Cozy Unique Rustic Modern. These all describe the Random Cabin. In the small inviting village of Random Lake sits a small but mighty house. 2 bedrooms, beautiful kitchen, tree fort style loft, 2nd living/kid room w/ arcade & pinball. Everything you could want. Fish off the pier or use our kayaks to explore the lake. Ride our bikes around town & then cuddle up in front of the fireplace. The village beach is only a few blocks away, so is the bustling downtown. Memories await

Top Guest favourite

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.

Apartment in Sheboygan

4.98 out of 5 average rating, 217 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!

Top Guest favourite

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

4.97 out of 5 average rating, 319 reviews

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.

Guest favourite

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

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!*

Guest favourite

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.

Home in Sheboygan

4.86 out of 5 average rating, 218 reviews

Dog Friendly Cozy Cottage Rental on Lake Michigan!

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Top Guest favourite

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

4.96 out of 5 average rating, 173 reviews

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.

Guest favourite

A bright seating area features two modern armchairs and a cozy rug. Large glass doors frame views of the beach, allowing natural light to fill the space. A tall bookshelf holds books and decorative items, while a TV is positioned for entertainment.

Condo in Sheboygan

4.96 out of 5 average rating, 141 reviews

Tropical condo w/ beach access & fireplace

Warm lake breezes by day and cozy evenings indoors set the tone at this upper-level condo near Lake Michigan. Thoughtfully equipped and walkable to the waterfront, it’s an easygoing retreat for couples, families, or remote work stays. - Sleeps 5 | 2 bedrooms | 4 beds | 1 bath - Lake view from front & rear private balconies - Waterfront location w/ shared beach access - Electric fireplace & Roku TV - Kitchen, bathroom essentials & in-unit laundry - Beach essentials & dedicated workspace

Top Guest favourite

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.

Loft in Sheboygan

4.97 out of 5 average rating, 116 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.

Top Guest favourite

An outdoor fire pit is surrounded by four wooden Adirondack chairs, set against a backdrop of snow-covered rocks and bare trees. The cabin, with its rustic wooden structure and metal roof, is visible in the background under a clear blue sky.

Cabin in Oostburg

4.94 out of 5 average rating, 138 reviews

Forest cabin near Kohler-Andrae w/ hot tub

Welcome to Pine Dunes Cabin, a cozy forest retreat just steps from Lake Michigan - perfect for relaxed group getaways year-round. Tucked among trees on a quiet stretch of land, this cabin blends space, comfort, and nature. - Sleeps up to 10 | 4 bedrooms | 7 beds | 3 baths - Seasonal hot tub (Nov–Apr) & outdoor fire pit - 3 decks + large three-season room - Fully equipped kitchen & spacious dining - Smart TVs, WiFi & loft hangout space - Beach essentials & easy lake access

Guest favourite

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.

Apartment in Sheboygan

4.93 out of 5 average rating, 548 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 favourite

A welcoming living area is highlighted by a warm orange couch with blue accent pillows. A modern lamp with a red base stands beside it on a side table. A framed painting adds character, while a plant is visible through a doorway leading to another room.

Home in Sheboygan

4.94 out of 5 average rating, 138 reviews

King Bed Near Lake w/ Fire Pit & Pack N Play

Welcome to the Getaway! Getaway: noun - an act or instance of getting away; a place suitable for a vacation You will unwind in this peaceful 3 bedroom lower unit near Lake Michigan, Whistling Straits and Kohler/Andrae State Park. You can enjoy an evening around the fire pit, or if you don’t feel like staying in, 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.