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Vacation rentals with a patio in Sheboygan

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Top-rated patio rentals in Sheboygan

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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

4.93 out of 5 average rating, 103 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

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 Sheboygan

4.95 out of 5 average rating, 39 reviews

The perfect location!

You will be close to everything when you stay at this 1930s home. Walk three blocks west to Sheboygan's historic downtown to find shops, restaurants, theaters, museums, and a local farmer’s market. Walk two blocks east to the beach, walking/biking trail, marina, and parks. Free street parking, 1-stall attached garage, reliable wifi. All three bedrooms and full bathroom are upstairs. Washer/dryer and 1/2 bath are in the basement. Three window AC units in the summer. Kitchen has basic amenities.

Top guest favorite

A spacious stone home is nested within expansive green lawns and lush trees, offering a serene countryside backdrop. The property features a private basketball court in the foreground, and the house is highlighted by warm lighting from the windows, creating a welcoming atmosphere.

Castle in Cleveland

4.99 out of 5 average rating, 154 reviews

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

Top guest favorite

A cozy living area is filled with neutral-toned furniture, including a large sofa, accent chairs, and a circular coffee table. Natural light filters in through large windows, highlighting the wooden floors and a decorative area rug beneath. Soft green accents are present in the lamps and curtains.

Home in Sheboygan

4.97 out of 5 average rating, 109 reviews

House Near the Lake

Get out and enjoy nature, then return to a quiet mix of modern and retro in this family home only a block away from Lake Michigan. There are three parks and two beaches within a mile, as well as Terry Andrae State Park about 10 minutes away. If the outdoors aren't your thing, downtown Sheboygan hosts the Kohler Art Center, The Weil Center, Blue Harbor, and the Children's Museum, with Road America only 30 minutes away. Located between Milwaukee and Green Bay, this home has all the conveniences.

Home in Cleveland

4.91 out of 5 average rating, 32 reviews

Private lake home near Whistling Straits Kohler

Walk to your private beach without a bluff! Lakeglass Cottage is situated on 5 beautiful acres with over 300 feet of private beach. Offering breathtaking views of Lake Michigan, easy water access, 2 acres of flat lawns, walking trails through woods and prairies, and ample parking. This luxuriously appointed mid century modern home has everything you need and is just feet away from the beach. Lakeglass Cottage is the perfect place for you to relax and make precious memories with your family.

Top guest favorite

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.

Apartment in Sheboygan

4.97 out of 5 average rating, 112 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.

A inviting living area features a light-colored leather sofa adorned with soft throws. A coffee table displays a decorative arrangement of natural elements. Two windows allow natural light to fill the space, and a bookshelf holds various items, enhancing the room's charm.

Home in Plymouth

4.92 out of 5 average rating, 119 reviews

Vintage Farmhouse on Blueberry Hill.

Relax with the whole family at this peaceful place to stay. Located conveniently half way between Green Bay and Milwaukee. Find your self minutes away from Road America, Whistling Straits, snowmobile trails, kettle moraine state forest, and so much more. Our property has walking trails to the river, throughout the woods and around the creek area, This winter you would have the opportunity to snowshoe our 103 acre property, or break your own cross country ski trail! Or just a quiet getaway!

Top guest favorite

A well-appointed bedroom features a spacious bed with white linens and a textured gray throw. Two decorative lamps provide soft lighting on either side of the bed. Bright windows are framed by patterned curtains, and wall art adds a touch of elegance to the neutral-colored walls.

Apartment in Sheboygan

4.96 out of 5 average rating, 49 reviews

Peaceful apartment close to the lake

Beautiful, newly furnished & updated, 2 Queen bedroom upper apartment with large closets, 1 bath, desk with workspace, stocked kitchen, in unit laundry, private balcony, high speed internet, 2 Smart TVs, keyless private entrance Central downtown location walking distance to restaurants/bars, parks, the beach, festivals, Museums, Arts Centers, Stephanie H. Weill Center & more! 10-15 min. driving distance to Kohler golf courses, The Bull at Pinehurst Golf Course, Road America, Elkhart Lake

A cozy backyard oasis is illuminated in evening light, featuring comfortable seating around a fire pit. An outdoor movie screen projects a vibrant image onto the adjacent wall, surrounded by lush landscaping and wooden fencing that enhances privacy.

Home in Sheboygan

4.95 out of 5 average rating, 132 reviews

LUX Downtown Escape | Outdoor Movie Screen

Welcome to our beautiful 2-bedroom historic home in Downtown Sheboygan! This charming and well-appointed residence offers a comfortable and stylish stay for your visit to the area. From the Chef’s kitchen, comfortable living room, and peaceful backyard, to its prime location within walking distance of Sheboygan's vibrant nightlife, theater, and restaurants, you'll have everything you need right at your doorstep. The home is also just a few blocks from Lake Michigan's beautiful beaches.

Top guest favorite

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.

Apartment in Sheboygan

4.98 out of 5 average rating, 170 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.

Top guest favorite

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 Sheboygan

5 out of 5 average rating, 29 reviews

Beachside, Chefs Kitchen, High-End Everything

🏖️ 1 Block from Sheboygan’s Best Beach & Lakeshore Walks 🍽️ Chef's Kitchen with High-End Appliances & Tons of Space 🪑 Ultra-Luxe MillerKnoll Seating + Custom Handcrafted Beds 🎨 Local Artisan Artwork & Designer Wood Furniture Throughout 🚲 Free Bikes + Walkable to Downtown, Riverfront & Pier 🛋️ Bright Open Layout 🏡 Charming & Safe Historic Ellis District Neighborhood 🚎 Summer Trolley, Public Bus & Scooters Nearby 📶 Fast WiFi

A green chair is positioned next to a circular mosaic table, offering a spot to relax. In the background, a wooden railing encloses a patio area with additional seating visible. Lush greenery from surrounding trees adds a natural touch to the inviting outdoor space.

Home in Sheboygan

4.9 out of 5 average rating, 140 reviews

Spacious Home Near Lake MI w/ Fire Pit

Welcome to the Relax ‘n Retreat! Retreat: noun - a quiet or secluded place in which one can rest and relax Unwind at our 3 bedroom home 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. Send me a message to find out about our other available listings.

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Popular amenities for Sheboygan patio rentals

Free parking on premises

Air conditioning

Apartment rentals with a patio

Top guest favorite

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.

Apartment in Sheboygan

5 out of 5 average rating, 79 reviews

Recombobulation Station-Locally Owned Surf Escape

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.

Apartment in Sheboygan

4.79 out of 5 average rating, 24 reviews

On Broadway

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.

Apartment in Sheboygan

4.91 out of 5 average rating, 22 reviews

Home away from home

A fully equipped kitchen is featured, showcasing dark wooden cabinetry and stainless steel appliances. A round wooden dining table with four matching chairs is positioned nearby. Natural light filters through a window adorned with light curtains, illuminating the warm tones of the flooring.

Apartment in Sheboygan

4.85 out of 5 average rating, 80 reviews

Fully Loaded and Clean! King

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

4.96 out of 5 average rating, 51 reviews

The Cozy Country Farmhouse, Eisenbahn Suite

Top guest favorite

Apartment in Sheboygan

5 out of 5 average rating, 22 reviews

Clean, Comfy Stay Near Parks, Downtown & Lake!

A kitchen features light green walls and wooden ceiling beams, enhancing a spacious layout. Modern appliances are complemented by white cabinetry and a large island with bar seating. Natural light fills the room through multiple windows, providing an inviting space for meal preparation.

Apartment in Sheboygan Falls

5 out of 5 average rating, 4 reviews

The Historic Downtown Suite

Apartment in Sheboygan

New place to stay

Beach town bungalow

House rentals with a patio

Top guest favorite

The main living area features a mix of seating options, including a modular sectional sofa and lounge chairs. A decorative area rug sits under a circular coffee table, while large windows offer views of the surrounding greenery. A fireplace enhances the inviting ambiance.

Home in Sheboygan

5 out of 5 average rating, 30 reviews

Norwind Ranch - Peaceful Retreat Near Road America

The exterior of the house showcases a charming combination of brick and stucco with a classic gabled roof. Well-kept landscaping includes a small evergreen tree and planters at the entryway. A clear path leads to the front door, with bins placed beside the house.

4.97 out of 5 average rating, 32 reviews

The Kohler House

Top guest favorite

A two-story home is seen with gray siding and brown shutters, featuring a covered front porch supported by wooden columns. Lush green shrubs and flower beds line the walkway, while a well-maintained lawn extends around the property. A car is parked in the driveway.

Home in Random Lake

4.93 out of 5 average rating, 60 reviews

Oma's Beach House

Top guest favorite

A charming bungalow is framed by a large tree with purple leaves, featuring a neatly maintained lawn and bordered by low shrubs. The entrance is welcoming, with a pathway leading to the front door, and an inviting porch area is visible.

Home in Sheboygan Falls

4.99 out of 5 average rating, 94 reviews

Adorable bungalow in historic Sheboygan Falls,WI

A spacious backyard is visible, featuring a circular stone fire pit surrounded by wooden Adirondack chairs. A deck with a gazebo is seen in the background, alongside the two-story house. Lush green grass and trees enhance the outdoor setting.

Home in Sheboygan

4.82 out of 5 average rating, 33 reviews

*Centrally Located and Updated* The Barrel House

An outdoor seating area is arranged in a circular formation around a fire pit, featuring multiple adirondack chairs. A picnic pavilion with a wooden roof is positioned in the background, surrounded by lush greenery, creating a peaceful atmosphere for gatherings.

Home in Sheboygan

4.94 out of 5 average rating, 34 reviews

State Park w/ Orchard Style Yard & Pavilion

Top guest favorite

A spacious living area is centered around a circular glass table with a potted plant. Comfortable gray sofas frame the space, accompanied by two blue chairs. A stone fireplace adds warmth, and large windows allow natural light to fill the room, displaying views of the outdoors.

Home in Cleveland

4.99 out of 5 average rating, 74 reviews

Wake on the Lake - Minutes to Whistling Straights

Top guest favorite

A newly built farmhouse is set against a clear blue sky, featuring a covered porch that runs the length of the building. Well-maintained grass surrounds the structure, complemented by a gravel pathway and landscaped rocks. A vehicle is parked nearby, adding to the rural ambiance.

Home in Sheboygan

5 out of 5 average rating, 37 reviews

Private 3 bd country home 2 miles N of Kohler WI

Condo rentals with a patio

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.

Condo in Sheboygan

5 out of 5 average rating, 6 reviews

Welcome to our Cozy Lake Condo!

Top guest favorite

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.

Condo in Sheboygan

4.98 out of 5 average rating, 46 reviews

A Glorious Getaway Sheboygan - LUX Lake Condo

A modern living area is presented with a spacious layout, featuring comfortable dark gray recliners and a coffee table set atop a colorful area rug. The kitchen is visible in the background, showcasing sleek cabinetry and contemporary appliances. Original artwork decorates the walls.

Condo in Sheboygan

5 out of 5 average rating, 4 reviews

Luxurious Artistic modern 2bed2bath condo

Top guest favorite

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.

Condo in Sheboygan

4.95 out of 5 average rating, 56 reviews

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

Top guest favorite

A spacious guest room features a queen size bed with a patterned blanket and blue pillows. A large window with natural light looks out towards the prairie. A sitting area with a blue chair and a work desk is highlighted, along with bedside lamps and a dark dresser.

Private room in Kewaskum

4.94 out of 5 average rating, 70 reviews

Condo in the Kettle Moraine

A large multi-level home is surrounded by a neatly landscaped yard. The exterior features a beige siding with brown accents and a two-car garage. A wooden deck with railings and planters complements the front entrance, while a smooth driveway leads to the house.

Private room in Elkhart Lake

4.89 out of 5 average rating, 18 reviews

Quiet Country Setting- Downstairs Apartment

A cozy bedroom features a spacious bed with a light-tone blanket, complemented by two wooden nightstands. A large window with a sliding door offers access to a balcony. Dark curtains frame the window, and a flat-screen television rests on a wooden dresser.

Condo in Elkhart Lake

4.27 out of 5 average rating, 15 reviews

Siebkens 1 bedroom condo

An open layout features a cozy sleeping area with a spacious bed framed by light walls and large windows. A modern kitchen with dark cabinetry and stainless steel appliances is complemented by a round coffee table on a textured area rug. A comfortable seating area is visible.

Condo in Elkhart Lake

5 out of 5 average rating, 5 reviews

Private Beach, Pools & Full-Kitchen

Quick stats about vacation rentals with a patio in Sheboygan

Total rentals
170 properties
Nightly prices starting at
€ 34 before taxes and fees
Total number of reviews
8.7K reviews
Family-friendly rentals
140 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
100 properties have a dedicated workspace

Destinations to explore