Vacation 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, 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!

4.99 out of 5 average rating, 323 reviews

Cabin in Elkhart Lake

Elkhart A-Frame, Wooded Retreat near Road America

The Elkhart A-Frame is an ideal location for the adventure seeker who wants a unique and private experience that is still close to all the action. The home sits on a wooded three-acre private retreat only about a mile from the village of Elkhart Lake, Road America, and Golf Courses. This unique cabin was built in the 1970's but has been recently renovated with a fun Scandinavian modern flair. It has all the amenities for a memorable vacation stay that provides plenty of epic photo opportunities.

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, 129 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.

An indoor relaxation area features a hot tub with bubbling water, illuminated in soft green light. A dry sauna is visible in the background behind a glass door. Two chairs with patterned cushions are positioned nearby, alongside a neatly organized shelf with rolled towels.

4.98 out of 5 average rating, 247 reviews

Boutique Wellness Retreat - Hot Tub and Fireplace

Enjoy Sheboygan in this beautiful boutique home. New patio and deck! Hot tub/Dry Sauna! Comfort and charm throughout. Cooks kitchen with all amenities. Primary bedroom w/King size bed. Secondary bedroom has 2 twin beds. The beautiful fireplace in the living room is perfect for a relaxing couples evening. Enjoy a glass of wine or local brew on the patio while you grill out. EV Charger and E-Bikes to explore the area. This beautiful boutique home is sure to impress! Let us help make it a memory.

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

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 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.

4.96 out of 5 average rating, 140 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

4.94 out of 5 average rating, 156 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.

4.95 out of 5 average rating, 234 reviews

Home in Plymouth

Wyatt's Country Home - King Bed

Soak up the modern vintage charm of our fully remodeled and updated home! Thank you for choosing our sparkling clean space. Our home is nestled on two quiet acres just north of Plymouth in the peaceful country. Enjoy coffee as the sun rises from one of the two decks, or perhaps a cocktail by the fire as the sun sets. We ourselves lived in this home for our first 5 years and turned it into a beautiful and peaceful space for ourselves that we would now like to share with everyone.

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, 187 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.

4.94 out of 5 average rating, 137 reviews

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

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

Popular amenities for Sheboygan outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.97 out of 5 average rating, 33 reviews

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.

Home in Kohler

The Kohler House

5 out of 5 average rating, 11 reviews

Home in North Point

A Cozy Lake Break

4.97 out of 5 average rating, 190 reviews

The kitchen features dark cabinetry with artistic landscape designs and a large white countertop island. Stainless steel appliances include a stove and dishwasher, while a coffee maker is positioned on the counter. Natural light enters through a nearby doorway, illuminating the warm wood tones of the floor.

Home in Plymouth

The 2400 sq ft Plymouth Paddock near Road America!

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, 26 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.

4.9 out of 5 average rating, 50 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

4.99 out of 5 average rating, 84 reviews

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

Wake on the Lake - Minutes to Whistling Straights

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

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, 30 reviews

Terrace View a Charming 1 Bedroom Apt

A living room is presented with a flat-screen TV mounted on a white unit. A gray sofa and a blue accent chair offer comfortable seating, while a coffee table with decorative items occupies the center. Natural light enters through a nearby window.

4.63 out of 5 average rating, 19 reviews

Sheboygan Getaway with Yard: 1 Mile to Lake Michigan

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, 50 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, 104 reviews

GGG Spacious Log Cabin apartment on the IAT

5 out of 5 average rating, 32 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

4.97 out of 5 average rating, 145 reviews

A wooden table displays a variety of items: an open book, a lime, a glass filled with dark liquid, and a bottle of rum beside a vintage Coca-Cola. A bouquet of vibrant flowers sits neatly in the background, with light filtering through a window.

Apartment in Kohler

The Hemingway on Church - It Tolls For Thee

Condo rentals with outdoor seating

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

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, 70 reviews

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

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

An aerial view captures the expansive sandy shoreline of Lake Michigan, bordered by lush green parkland. The shoreline is framed by a calm blue lake under a clear sky. Nearby, a modern white building is nestled among trees, providing access to the beach.

4.97 out of 5 average rating, 175 reviews

Quiet condo w/ decks & beach access

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.