Vacation rentals with outdoor seating in Sheboygan

4.99 out of 5 average rating, 306 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.

4.98 out of 5 average rating, 103 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.

4.97 out of 5 average rating, 117 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.

Apartment in Ellis Historic

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.

4.98 out of 5 average rating, 124 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.

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, 216 reviews

Dog Friendly Cozy Cottage Rental on Lake Michigan!

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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.

4.95 out of 5 average rating, 136 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, 179 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 hot tub, illuminated with soft blue lights, features cascading water and inviting seating. Adjacent, a traditional sauna with wood paneling provides a relaxing retreat. Decorative cushions accent modern chairs nearby, enhancing the tranquil space.

4.98 out of 5 average rating, 223 reviews

Boutique Wellness Retreat - Hot Tub and Fireplace

Enjoy this beautifully boutique home. New patio and deck! Hot tub/Dry Sauna! Comfort and charm throughout. Cooks kitchen with all amenities. Primary bedroom with 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. Sonos audio throughout. This beautiful boutique home is sure to impress!

5 out of 5 average rating, 182 reviews

Cabin in Cascade

hot tub and sauna on 5 private acres

Looking for a cozy winter retreat? Experience the Bird House, a tranquil Scandinavian-inspired private woodland paradise. Melt away stress in the hot tub and infrared sauna as you take in peaceful views of the meadow. Explore snowshoe and cross-country ski trails nearby in the scenic Kettle Moraine. Stream your favorite movie on the projector near the fireplace or unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee.

4.99 out of 5 average rating, 100 reviews

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

Adorable bungalow in historic Sheboygan Falls,WI

Cute bungalow located on a quiet cul-de-sac with a relaxing pond and a large fenced in yard. Centrally located within 20 minutes of Elkhart Lake, Whistling Straits and the shores of Lake Michigan. Also, it is a quick walk to quaint Downtown Sheboygan Falls where there is plenty of shopping, dining, parks, the Sheboygan River, and waterfalls. I also run a company called Rescue Dog Properties and will be donating 5% of all bookings to Paws Up Pet Rescue based in Sheboygan.

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, 206 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.

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.

4.9 out of 5 average rating, 145 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.

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, 184 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!

4.94 out of 5 average rating, 16 reviews

Home in North Point

Beach Break - Historic Home Meets Modern Comfort

5 out of 5 average rating, 56 reviews

Home in Ellis Historic

Art Collector's Dream - Remodeled w/ Gallery Vibes

4.98 out of 5 average rating, 139 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

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.

4.94 out of 5 average rating, 35 reviews

State Park w/ Orchard Style Yard & Pavilion

The dining area features a wooden table set with dark bowls and glassware, illuminated by a soft, modern light fixture. Natural light filters in through two large windows, casting a warm glow on the space. A decorative runner is placed center on the table.

5 out of 5 average rating, 25 reviews

Stylish brick cottage - family & pet friendly

A spacious living area features a light-colored sectional sofa with various accent cushions, arranged on a plush area rug. Dark wooden beams and a stylish coffee table enhance the modern decor. An inviting atmosphere is created by soft ceiling lights and neutral wall tones.

5 out of 5 average rating, 28 reviews

Fairway Getaway

4.96 out of 5 average rating, 205 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, 79 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.

4.96 out of 5 average rating, 24 reviews

Terrace View a Charming 1 Bedroom Apt

Superhost

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 w/ Yard: 1 Mi 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.

4.91 out of 5 average rating, 32 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

4.99 out of 5 average rating, 155 reviews

A warm and inviting bedroom is framed by sliding barn doors, revealing a spacious bed with white bedding. Two bedside tables, each adorned with a lamp, provide light. Natural light enters through two windows, accentuated by wooden trim and classic blinds.

Apartment in Kohler

Washington Walk Historic House w/elegant spa bath

4.96 out of 5 average rating, 52 reviews

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

The Cozy Country Farmhouse, Eisenbahn Suite

5 out of 5 average rating, 25 reviews

Clean, Comfy Stay Near Parks, Downtown & Lake!

Condo rentals with outdoor seating

The exterior of a charming building is presented, featuring a distinctive red roof and white siding. A reserved parking space is visible in the foreground, along with colorful flowerbeds that add a vibrant touch. The entrance is framed by a spacious porch, leading to the main entrance.

Condo in Campbellsport

5 out of 5 average rating, 4 reviews

2BR Condo on a resort on the lake w/beach access

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, 48 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.

4.94 out of 5 average rating, 36 reviews

Heavenly Condo in the Malibu of the Midwest

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 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.

4.95 out of 5 average rating, 61 reviews

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

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, 111 reviews

Janelle's Dockside Condo

4.95 out of 5 average rating, 80 reviews

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

Condo in the Kettle Moraine