Holiday rentals with a patio in Sheboygan

4.92 out of 5 average rating, 13 reviews

Storybook Home - 1 mi to Lake & Downtown Sheboygan

Welcome to The Fox & Folly Inn 🦊 —a unique whimsical retreat. Perfect for families and those who are kids at heart! 🖼️ Creative and cozy home with art and murals. 🦊🐰🦉Themed with original characters. Audio stories & endless charm! 🛏️ Master Bedroom - King Bed 🛋️ 2nd Bedroom - Bunk Bed = Full Lower, Twin Upper 🛌 Sleeps 5 🛁 1 Full Bathroom - Towels, Hair Dryer+ 🍽️ Fully Stocked Kitchen 🅿️ Off-Street Parking 🏖️Minutes from the beach & Bookworm Gardens 📖Your storybook adventure awaits!

4.98 out of 5 average rating, 234 reviews

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.

Flat in Ellis Historic

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!

4.94 out of 5 average rating, 108 reviews

A charming log cabin features rustic wooden architecture, complemented by red window frames. Surrounded by lush greenery, the structure offers a welcoming front porch. Natural light bathes the exterior, enhancing the serene setting among the trees, with a pathway leading to the entrance.

Cabin in Campbellsport

Wooded CABIN-Sunset & Lake Views/Kayak to Tiki Bar

Slow down at Fraser Fir log cabin, built in 1958 on Kettle Moraine Lake. In the summer, enjoy quiet moments watching the sun set from the front porch, then relax by the fire pit under a sky full of stars. Fish from the dock, kayak around the lake, or bring your boat to soak up the sun. In the winter, grab your ice-skates or ice-fishing gear and head out on the lake. With countless trails nearby, the hiking options are limitless and beautiful in every season. Your next adventure awaits.

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, 137 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.

4.91 out of 5 average rating, 129 reviews

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

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!

4.94 out of 5 average rating, 144 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

Cozy cabin w/ hot tub access & fire pit

Welcome to your cozy forest retreat near Lake Michigan - the perfect setting for relaxed group getaways in every season. Tucked among trees on a quiet road, this cabin blends space, warmth, and easy lake access: - Sleeps 10 | 4 bedrooms | 7 beds | 3 baths - Private hot tub - seasonal (Nov to Apr), fire pit & 3 decks - Shared beach access & lake access + beach essentials - Fully equipped kitchen, dining table & three-season room - Smart TVs, Wifi, central heating & central air conditioning

4.95 out of 5 average rating, 173 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, 192 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 bedroom features a spacious bed adorned with cotton linens, complemented by decorative pillows. Nightstands with lamps are placed on either side. A small television is mounted on the wall, while a white dresser provides additional storage. Light-colored flooring enhances the airy feel.

5 out of 5 average rating, 55 reviews

The Sheboygan Foodie Flat

Schnazzy upper flat in the heart of Sheboygan’s Eastside. Walk to Lake Michigan Beaches, Riverfront, Uptown and Downtown. Enjoy the newly renovated 2nd floor of an 1893 historic rambler, with lots of natural light. -Desirable Eastside, with walkable neighborhoods. -Large Italian tile walk-in shower with Kohler fixtures. -Fully equipped kitchenette with microwave, convection oven, two-burner hot plate, Keurig, coffee pot & toaster. -New furnishings -Sheboygan Foodie Guidebook

5 out of 5 average rating, 35 reviews

Clean, Comfy Stay Near Parks, Downtown & Lake!

Enjoy a peaceful stay near Sheboygan’s lakefront, family parks, and downtown eats. This clean, cozy 2BR unit offers everything you need—walkable location, garage parking, full kitchen, and thoughtful touches like old-school Nintendo and local recommendations. ⭐ “Clean, comfy, quiet—close to everything. We’ll definitely stay again!” – Roger ✓ Minutes to downtown & Lake Michigan ✓ Family park across the street ✓ Garage + easy onsite parking

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.

4.92 out of 5 average rating, 61 reviews

Sheboygan Riverside Condo

Experience the Malibu of the Midwest in this stunning 2-bedroom retreat! The king suite offers a private balcony with a cozy fireplace overlooking the serene Sheboygan River. The second bedroom features two queen beds, perfect for families or friends. Enjoy an open-concept living space, modern kitchen, and easy access to Sheboygan's best attractions. With a 2-car garage and nearby conveniences, this is your ideal getaway spot!

5 out of 5 average rating, 105 reviews

Home in Oostburg

Waterfront home w/ BBQ & lake access

Welcome to your Lake Michigan retreat - a peaceful waterfront escape designed for gathering, relaxing, and reconnecting by the water. - Sleeps 15 | 6 bedrooms | 11 beds | 3.5 baths - Waterfront w/ lake access, shared beach access - beachfront & beach essentials - Sauna w/ lake views & indoor fireplace - wood-burning - Fire pit, BBQ grill & private backyard - Children’s playroom, Wifi & free residential garage - 6 spaces

Popular amenities for rentals with patio in Sheboygan

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Flat rentals with a patio

5 out of 5 average rating, 92 reviews

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.

Flat in Ellis Historic

Recombobulation Station-In The Heart of Sheboygan!

5 out of 5 average rating, 11 reviews

A living room featuring large windows that provide views of the surrounding landscape. A patterned armchair invites relaxation alongside a small side table. A white fireplace serves as a focal point, with a stylish arrangement of decorative items above it. A soft area rug covers the hardwood floor.

Flat in Elkhart Lake

Resort Condo on Elkhart Lake

5 out of 5 average rating, 5 reviews

A decorative wooden sign displays the phrase 'Knot A Care by the Lake' in bold black letters. The sign features a braided rope design at the center, enhancing the nautical theme. The background is a light-colored wood, providing a contrasting framework for the text.

Flat in North Point

Knot A Care By The Lake

Superhost

A welcoming living area features a dark leather sofa and a recliner, arranged around a coffee table. A modern fireplace with a stone surround adds warmth, while large windows provide natural light. Two framed art pieces enhance the wall, creating a cozy atmosphere.

Modern Nomad - Monthly Rates Available!

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.

Flat in Kewaskum

The Cozy Country Farmhouse, Eisenbahn Suite

Superhost

4.5 out of 5 average rating, 4 reviews

Beach town bungalow

5 out of 5 average rating, 9 reviews

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.

Flat in Sheboygan Falls

The Historic Downtown Suite

4.96 out of 5 average rating, 92 reviews

A renovated historic home displays a charming exterior with wide steps leading to a wooden front door. Flanking the entrance, tall evergreen trees create a natural boundary. The building features multiple large windows, enhancing its traditional architectural style.

Flat in Ellis Historic

Quaint Blast from the Past - walk to lake/8th st

House rentals with a patio

4.94 out of 5 average rating, 50 reviews

Sheboygan Chalet | Nature, Arcade, Sauna & Hot Tub

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.

5 out of 5 average rating, 32 reviews

Norwind Ranch - Peaceful Retreat Near Road America

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, 34 reviews

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 Ellis Historic

Charming home w/ fireplace & backyard

The exterior of a spacious home is framed by mature trees and landscaped greenery. A large deck is visible on the upper level, featuring outdoor seating. A winding pathway leads to the entry, with a mixture of stones and garden beds enhancing the natural surroundings.

5 out of 5 average rating, 10 reviews

30 Second walk - Lake Michigan

4.94 out of 5 average rating, 68 reviews

A serene riverside view is framed by tall trees, showcasing a natural pathway leading to the water. A circular stone firepit is visible, complemented by two small white chairs, providing an inviting outdoor seating area.

Home in Sheboygan Falls

“On The Water” the Sheboygan River Overlook

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.

4.93 out of 5 average rating, 27 reviews

Relax & Play- Walking distance to food & drinks

5 out of 5 average rating, 20 reviews

The exterior of the house features a modern design with a combination of white siding and grey shingles. A welcoming porch is enhanced by decorative blue chairs and flowering plants, providing a cozy entrance. A clear driveway leads to the side of the property.

Home in North Point

Luxury 4B-2Ba Lake & Beach House

Apartment 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.

5 out of 5 average rating, 6 reviews

Welcome to our Cozy Lake Condo!

Apartment in Sheboygan

5 out of 5 average rating, 3 reviews

Beach Blues Condo - A Stay at Blue Harbor

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

5 out of 5 average rating, 5 reviews

Apartment in Sheboygan

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.

5 out of 5 average rating, 4 reviews

Luxurious Artistic modern 2bed2bath condo

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, 77 reviews

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

4.95 out of 5 average rating, 91 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