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, 223 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, 329 reviews

The A-frame cabin is framed by lush greenery and colorful landscaping. A welcoming pathway leads to the entrance, featuring a spacious deck. The cabin's dark exterior contrasts with the surrounding trees, creating a serene and private atmosphere.

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, 132 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 inviting wellness space features a hot tub with gentle bubbles and soft green lighting. Adjacent, a wooden dry sauna awaits, surrounded by potted plants. Comfortable seating with decorative pillows is arranged nearby, creating a serene atmosphere for relaxation.

4.98 out of 5 average rating, 256 reviews

Boutique Wellness Retreat - Hot Tub and Fireplace

Celebrate your special occasion in Sheboygan at 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. Let us impress you and help make it a memory.

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!

4.95 out of 5 average rating, 165 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 cozy two-story home nestled among tall trees, featuring a spacious front porch and a gravel driveway leading to a two-car garage. Lush greenery surrounds the property, providing a serene and inviting woodland atmosphere.

5 out of 5 average rating, 231 reviews

Woodland Creek Retreat: explore & relax!

Lovely home nestled in 9 acres of peaceful woodland. 1.5 miles off I-43. Enjoy a walk in the woods or enjoy the dunes and wonderful views of Lake Michigan from Terry Andrae State Park only .2 miles away! Enjoy relaxing on the front porch or taking in the view of the woods from the spacious back deck. Be on the lookout for turkeys and deer. Wonderful wood burning fireplace and extensive game collection(500+) for staying in! We love the cozy and open cabin feel and hope you will too!

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, 190 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.

The exterior of a charming house is depicted, showcasing a welcoming front porch with steps leading up. The porch features a small seating area and decorative plants, while lush green grass frames the path, adding to the inviting ambiance.

4.97 out of 5 average rating, 215 reviews

Logan's Guest Nest

Logan's Guest Nest is located in a nice small town feel area. With a small look on the outside your Nest has a big feel on the inside. Spacious rooms and quiet area to rest after a day at the many beaches lining Lake Michigan. Or coming back from the races at Road America. Not to mention a day of golf at the many area courses, Whistling Straits maybe. All these wonderful outings are just minutes from the Nest. Plenty of local dinning or delivery for a nice ending of the day.

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.

4.88 out of 5 average rating, 213 reviews

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.

Condo in Sheboygan

Beachside Lake View - 2br - First Floor - Garage

Located just one lot in from the beautiful shores or Lake Michigan. Amazing location provides year round stunning views . This is a lower 2 bedroom 1 bath condo in a 4unit building were all the units have the same basic layout. You can listen to the waves or walk just a few feet and have the sand on your feet. This condo features front and rear balconies. Makes for a great place to enjoy a weekend get away or a place to relax at night while on a business trip.

Popular amenities for Sheboygan outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

The living room features a light, airy space with a large window offering a view of Lake Michigan. A cozy white sofa is complemented by a striped chair, and a wooden coffee table holds decorative items. Soft lighting illuminates the room, enhancing its inviting atmosphere.

4.96 out of 5 average rating, 126 reviews

Bright and Beautiful Lake Escape

A spacious sunroom is filled with natural light from large windows and skylights. A comfortable gray sectional sofa surrounds a round coffee table, complemented by decorative pillows. Potted plants are placed nearby, enhancing the room's inviting atmosphere and offering views of the wooded surroundings.

5 out of 5 average rating, 30 reviews

Modern Lakeshore Home with Treehouse

4.97 out of 5 average rating, 192 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, 18 reviews

Home in North Point

Beach Break: Historic 2BR Home | Quiet & Walkable

A serene beach stretches along the shoreline, with gentle waves lapping at the sandy coast. The sky is painted with soft pastel hues as the sun sets, casting a warm glow over the water. A few trees line the beach in the distance.

5 out of 5 average rating, 15 reviews

Clara Vida Inn- 1/2 Block from Lake and beach!

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!

A well-lit game room features an air hockey table with blue LED lighting, a green pool table, and a bar area with seating for four. A washer and dryer unit is positioned against the wall, while a television is mounted for entertainment.

4.96 out of 5 average rating, 26 reviews

Relax & Play- Walking distance to food & drinks

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

Apartment rentals with outdoor seating

4.99 out of 5 average rating, 93 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 / Coffeehouse / Kettle Moraine CF

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, 54 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

4.96 out of 5 average rating, 53 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, 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

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

4.96 out of 5 average rating, 142 reviews

Condo in Sheboygan

Lakeview condo w/ fireplace & workspace

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

4.94 out of 5 average rating, 90 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