Holiday rentals with outdoor seating in Sheboygan

Apartment in Ellis Historic

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, 221 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!

4.97 out of 5 average rating, 320 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 bright living area showcases a spacious dining table with place settings, and a cozy red armchair positioned nearby. Large sliding doors reveal an inviting patio space, while a television stands against the wall opposite, enhancing the relaxing atmosphere.

4.97 out of 5 average rating, 111 reviews

Relaxing Sheboygan/Kohler Getaway

Newly remodeled townhouse with all the comforts to make you feel at home in quiet neighborhood, boasting a spacious backyard w/patio, fire pit & free parking. Amenities include well-equipped kitchen, 2 BR & 2 BA, washer/dryer, wi-fi, & smart TV. Conveniently located within minutes to Village of Kohler, Downtown Sheboygan & Lakefront, Black Wolf Run, Whistling Straits (14 min), Road America (18 min), Kohler-Andrae State Park (16 min), grocery stores, restaurants, shopping & local entertainment.

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.

4.98 out of 5 average rating, 131 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.

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!

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4.72 out of 5 average rating, 139 reviews

An aerial view captures the layout of the property, showcasing a cluster of buildings surrounded by lush greenery and a small pond. Farm fields extend in all directions, while trees add a touch of vibrant color to the landscape.

Barn in Sheboygan Falls

Quiet Country Charm

Cozy barn loft with rustic charm. This newly renovated private loft sleeps 4 with the possibility of 1 or 2 more if you don’t mind sleeping on an air mattress. This room includes a bathroom with shower and small efficiency kitchen with microwave, coffee maker, and small refrigerator. The futon pulls out to a double bed. This relaxing local comes complete with barnyard animals for an authentic Wisconsin experience! You won’t forget the peaceful surroundings of this rustic destination.

A bridge is seen raised, allowing a sailboat to pass through the waterway. Clear blue skies provide a backdrop to the scene, while trees with autumn foliage line the riverbank. The calm water reflects the colors of the surroundings.

4.95 out of 5 average rating, 115 reviews

Janelle's Dockside Condo

GREAT LOCATION!! Built in late 2020. Come visit our luxury, "Nautical Themed" 2 bedroom condo in Sheboygan, WI located on the confluence of Lake Michigan and the Sheboygan River in the charming South Pier District. Relax on the deck with a beverage and watch the sailboats pass by. Stroll the boardwalk for fine dining, charter fishing, quaint boutiques or an afternoon ice cream. World class golfing at Black Wolf Run or Whistling Straights. Equipped with everything you need and more!

4.94 out of 5 average rating, 162 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.

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, 189 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 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.

4.94 out of 5 average rating, 144 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.

The image captures a scenic view from the deck, showcasing a lush green backyard leading to the shoreline of Lake Michigan. A fire pit is visible on the grass, and white planters frame the deck, while the sky displays a soft gray hue.

4.94 out of 5 average rating, 210 reviews

Walk-Out Lake Michigan Beach • Fire Pit • Sleeps 8

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.

4.95 out of 5 average rating, 144 reviews

*Front porch, fenced in backyard- PetsWelcome*

Peaceful bohemian retreat with a lively vibe! Perfect for couples, remote workers, girls weekends, golf outings and families! A short walk /bike ride downtown, to the lake or farmer's market. Visit locally owned shops and the world-renowned Kohler Art Museum. Only a 10 minute drive to the famous Whistling Straits/Irish golf course or Kohler Water Spa. Whatever brings you here, we look forward to your visit. Come and enjoy everything Sheboygan has to offer!

Popular amenities for Sheboygan outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

5 out of 5 average rating, 11 reviews

Home in North Point

A Cozy Lake Break

4.94 out of 5 average rating, 18 reviews

Home in North Point

Beach Break - Historic Home Meets Modern Comfort

4.98 out of 5 average rating, 100 reviews

Home in Elkhart Lake

Fernwood Lodge Elkhart Lakehome: pier, kayaks, tub

5 out of 5 average rating, 26 reviews

A two-story cottage is depicted, featuring a spacious deck and an outdoor grilling area. Surrounding greenery offers shade, while a clear view of the driveway is visible. Stairs lead toward the entrance. The structure showcases a combination of light-colored siding and contrasting railings.

Home in Oostburg

Due to cancellation 4th of July Available!

4.98 out of 5 average rating, 141 reviews

The two-story home features a beige exterior with multiple windows, surrounded by a grassy yard. Two chairs are positioned in front on a small patio area. Large trees provide shade, while a view of the countryside and other structures is visible in the background.

Home in Glenbeulah

Stay at Sunrise LLC, Like being at Grandma's

5 out of 5 average rating, 27 reviews

Family Cottage, Walk to the lake (pet friendly)

A serene bedroom is furnished with a spacious bed adorned with decorative pillows. Large glass doors open to a private balcony, while a comfortable armchair and a small tabletop are positioned near the window, allowing natural light to fill the room.

4.91 out of 5 average rating, 53 reviews

Sheboygan Riverside Condo

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

Apartment rentals with outdoor seating

4.99 out of 5 average rating, 92 reviews

A two-story brick building houses a coffee shop on the ground floor, featuring large windows flanked by a striped awning. The entrance is highlighted by a sign that announces it as Kettle Moraine's Favorite Espresso Bar. A welcoming atmosphere is created by its corner placement and outdoor seating area.

Apartment in Kewaskum

Local Landmark CF / Coffeehouse / Kettle Moraine

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

A modern kitchen features gray cabinetry and a spacious island with seating for two. Stainless steel appliances, including a microwave and stove, are visible. Natural light filters through a nearby window, and a floral centerpiece adds a touch of color to the countertop.

4.97 out of 5 average rating, 32 reviews

Terrace View a Charming 1 Bedroom Apt

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, 53 reviews

Parkside Studio Apartment

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, 105 reviews

GGG Spacious Log Cabin apartment on the IAT

5 out of 5 average rating, 38 reviews

A front porch is adorned with hanging flower baskets filled with red blooms, complementing the surrounding garden of hydrangeas and lilies. The spacious porch features multiple seating arrangements, welcoming guests to enjoy the peaceful outdoor setting.

Apartment in Plymouth

Private Retreat near Road America and Elkhart Lake

5 out of 5 average rating, 34 reviews

Clean, Comfy Stay Near Parks, Downtown & Lake!

Apartment in Sheboygan Falls

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.

5 out of 5 average rating, 8 reviews

The Historic Downtown Suite

Condo rentals with outdoor seating

Condo in Campbellsport

Lakefront Condo w/ Beach Access in Campbellsport!

A comfortable living area is furnished with a navy blue sofa and matching armchair, arranged around a coffee table. A flat-screen TV is mounted on the wall, while large glass doors provide access to a patio with outdoor seating, allowing natural light to fill the space.

4.73 out of 5 average rating, 15 reviews

Modern 2 Bedroom Condo with Lake Michigan View

Superhost

Condo in Sheboygan

New place to stay

A Glorious Getaway Sheboygan - LUX Lake Condo

An open-concept living area features a cozy gray sofa and a round dining table with light-colored chairs. A modern electric fireplace is positioned beneath a large wall-mounted TV. Natural light floods in through expansive sliding glass doors, leading to a furnished balcony.

4.86 out of 5 average rating, 22 reviews

Modern South Pier Condo on Sheboygan River!

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

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.

4.96 out of 5 average rating, 72 reviews

Amazing views beach condo for 12: 4 bdrm, 3 bath

4.97 out of 5 average rating, 175 reviews

A cozy living area features a light beige sofa paired with a stylish accent chair in green. A wooden coffee table sits on a textured area rug, while large sliding doors let in natural light and provide views of the outdoor space.

Condo in Sheboygan

Cozy lakeside condo w/ fireplace