Pet-friendly vacation rentals in Sheboygan

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.

A wooden shelf is mounted on a gray wall, displaying a collection of colorful ceramic mugs hanging from hooks. Above the mugs, a white container holds green plants, while a coffee bag is placed alongside framed artwork.

4.94 out of 5 average rating, 259 reviews

Dog Friendly Blue Door Cottage / Fully Fenced Yard

Nobody should have to leave their fur baby behind while on vacation. This is exactly why we created this comfortable home with your family & puppy in mind. You'll be at ease knowing that your pooch will be having just as much fun as you are. Modern hints are complemented by the cozy, welcoming decor found throughout. The coffee bar is a fav for any morning person, and the "take-a-wine leave-a-wine" wine bar offers evening excitement! The huge yard features a fire pit, gas grill, & cornhole.

4.9 out of 5 average rating, 109 reviews

A cozy living room is featured, with a dark sofa, light-colored chairs, and a round pouf. A woven pendant light hangs above, illuminating textured wall art. Natural light filters through multiple windows, highlighting a striped area rug laid on the wooden floor.

Apartment in Sheboygan

The Beach | Sheboygan 2Br/1 Ba

Welcome to the Beach, a lakeside retreat in the heart of Sheboygan. Located just 3 blocks from Lake Michigan and a stones throw to down town Sheboygan, The Beach is the perfect place to center your visit to Eastern Wisconsin. The Beach is the main floor unit of a duplex featuring 2 bedrooms, 1 bathroom, a well stocked kitchen, a cozy living room, fast wifi and convenient amenities. We have an easy check out with no to-do lists. Just pack and go! *New cleaning staff hired January 2023!*

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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4.95 out of 5 average rating, 154 reviews

A modern single-story home features a light gray exterior with a striking yellow front door. Large windows provide abundant natural light, while a well-maintained lawn is complemented by colorful flower beds. Skylights on the roof enhance the home's contemporary design.

Home in Cleveland

Modern Home Just 40 Minutes from GB NFL Draft

My home is just minutes from Whistling Straits Golf, Road America, Lake Michigan, Parks, Hiking, Biking, Snowshoeing, and Cross Country Skiing. You’ll love my place as it's newly remodeled, modern & cozy. The kitchen and living areas have high ceilings, sky lights & new furniture. The large outdoor living area is perfect for social time. My favorite is the heated bathroom floors. My place is perfect for golfers, wedding groups, couples, business travelers, and families (with kids & dogs).

Earthen home in Elkhart Lake

A spacious bathroom features wooden walls and ceilings, complemented by large windows providing expansive views of the surrounding landscape. Two circular sinks sit atop a rustic wooden vanity, while a freestanding tub is positioned near the window, enhancing the serene atmosphere. Decorative elements include a chandelier and potted plants.

4.97 out of 5 average rating, 108 reviews

Camp Skywood - Elkhart Lake - Road America

Nestled just minutes from Downtown Elkhart Lake, this custom-built cordwood home offers a secluded sanctuary experience. Perched atop a hill, the unique 16-sided house provides breathtaking views of the state forest and surrounding farmland. Despite its remote feel, you’re only a 5-minute drive from the charming Elkhart Lake business district. Day hikes on the ice age trail are just steps away from the property. Escape to tranquility while staying conveniently close to local attractions.

4.96 out of 5 average rating, 168 reviews

An aerial view of a spacious home is surrounded by mature trees, showcasing a private sandy beach alongside Lake Michigan. The property features a pathway leading to the house, emphasizing its secluded setting amid natural greenery.

Home in Oostburg

Lake Michigan Beach Home by Frank Lloyd Wright pro

Beautiful view and sand beach on Lake Michigan, completely private, surrounded by mature white pine trees and cedar trees. The spacious home is fully equipped with an "eat in" kitchen, dining room, and living room entertainment space, den with a see-through log-fired fireplace, screened-in porch to accommodate additional eating space, large outdoor deck with grill and fire pit. A canoe and a row boat are available for the boating enthusiast, with life jackets and other floating devices.

4.98 out of 5 average rating, 179 reviews

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.

Apartment in Sheboygan

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.

Apartment in Downtown Sheboygan

A compact kitchen area showcases modern cabinetry and essential appliances, including a refrigerator and a stove. A small counter with two stools provides a space for dining or working, accented by natural light filtering through a window. Decorative elements enhance the inviting atmosphere.

4.84 out of 5 average rating, 242 reviews

Sheboygan Surf House - Jetties

Located just 24 steps above Wisconsin's first Surf Shop, EOS Surf. Our Urban living oasis is a fully equipped studio apartment conveniently located in the heart of downtown, just steps from bars and restaurants and only blocks to Lake Michigan South Pier and Blue Harbor. Whether you are here for adventure sports like Surfing on the Great Lake, Kite boarding, charter fishing, a Wedding or leisure time SSH is perfect for you. Support Dog friendly

Guesthouse in North Point

A view of the serene shoreline along Lake Michigan is presented, framed by lush greenery. A blue railing leads down toward the beach, where sand and water are visible, inviting outdoor activities. The sky is overcast, creating a calm atmosphere.

4.82 out of 5 average rating, 490 reviews

Carriage House Sheboygan, Lake Mich beach access!

The Carriage House is the perfect getaway. Located in a beautiful historic neighborhood with Lake Michigan public beach access across the street, 100 yards away. Ideal for a family of four or an individual in town for business. Amenities have been thoughtfully placed to create the most comfortable and convenient stay for guests. We pride ourselves on ensuring you enjoy your stay with us and guarantee you'll love the neighborhood!

4.98 out of 5 average rating, 286 reviews

A quaint living space features an antique-style fireplace made of dark wood, with a circular mirror above it. A flat-screen television is mounted on the wall opposite a small table and a suitcase rests on the hardwood floor, accompanied by a decorative flower arrangement.

Apartment in Waldo

The Blue Cobb House

My place is close to 20 minutes south of Elkhart Lake and Road America. You’ll love my place because of the outdoors space, the comfy bed, and the kitchen. My place is good for couples, solo adventurers, and business travelers. The Blue Cobb House is about 15 minutes from Kohler-Andrae State Park and 30 minutes from Harrington Beach State Park. The Kettle Moraine area is just to our west and it is filled with hiking trails.

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 pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

A contemporary living area features a brown leather couch paired with green and gray cushions. A circular mirror is set above a wooden coffee table adorned with a small potted plant. The space includes hanging greenery and a soft area rug, enhancing a calm ambiance.

4.96 out of 5 average rating, 52 reviews

Sleeps 7{SPACIOUS}Pets Welcome!

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.

4.94 out of 5 average rating, 16 reviews

Relax & Play- Walking distance to food & drinks

4.57 out of 5 average rating, 23 reviews

A bright living space is captured, showcasing a light-filled area with wooden floors and beams. Comfy seating is arranged around a small table, inviting relaxation. The kitchen area has modern appliances, and a background glimpse of the shared recreation room is visible, featuring a pool table.

Home in Belgium

Lake Days+Game Nights at Cedar Beach

5 out of 5 average rating, 21 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

Winter's a good time to stay in&cuddle at Surfdaze

4.99 out of 5 average rating, 82 reviews

A spacious living area is highlighted by large windows allowing natural light to fill the room. Comfortable seating includes a sectional sofa and two armchairs, arranged around a stylish fireplace with intricate tile work. Light-colored curtains complement the modern decor.

Home in North Point

The Suncatcher -Steps from Lake - Fenced Yard

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

The kitchen features a spacious granite countertop and a black sink, highlighted by wooden cabinetry. A large window allows natural light to fill the room, showcasing scenic outdoor views. Colorful yellow chairs and a small table create a cozy seating area nearby.

4.97 out of 5 average rating, 135 reviews

Lakefront Charmer, cheerful decor gorgeous garden

4.99 out of 5 average rating, 79 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

Pet-friendly home rentals with a pool

A spacious living area showcases a beautiful wooden interior with large windows allowing natural light. Comfortable dark seating is arranged around a coffee table, complemented by a decorative rug. A flat-screen TV is mounted on the wall for entertainment.

Home in Kiel

4.94 out of 5 average rating, 16 reviews

Family Home w/ Indoor Pool ~ 2 Mi to Elkhart Lake!

A spacious room features a king-size bed with a textured blanket. Modern appliances, including a refrigerator, are visible. A television is mounted above a decorative fireplace, and a small desk with a chair is positioned nearby. Natural light is welcomed through a door leading to the outside.

Hotel room in Elkhart Lake

Sleeps 8! 2 Full Bath with Kitchenette!

Apartment in Elkhart Lake

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.

5 out of 5 average rating, 11 reviews

Resort Condo on Elkhart Lake

Hotel room in Elkhart Lake

A well-lit room features two spacious beds dressed in crisp white linens. A flat-screen television is mounted on the wall, while a dresser provides storage. A small desk is set against one wall, accompanied by a decorative indoor plant in a pot.

5 out of 5 average rating, 7 reviews

Resort Life 2 Queen Suite

Private, pet-friendly home rentals

4.98 out of 5 average rating, 51 reviews

A spacious living area features a stone fireplace surrounded by wood paneling and large windows allowing natural light. Cozy seating is arranged around a coffee table, with a television mounted above the fireplace. The décor includes welcoming signs and artwork, enhancing the rustic charm of the space.

Cabin in Valders

Cozy cabin in the woods

4.79 out of 5 average rating, 153 reviews

A spacious living area features large windows framing a serene lake view, reflecting shimmering sunlight. A comfortable white sofa is positioned in front of the window, accompanied by a patterned armchair. Natural light fills the room, enhancing the coastal atmosphere.

Home in Oostburg

Newly Renovated Beach Front Home in Oostburg WI

5 out of 5 average rating, 48 reviews

A spacious living area is observed, featuring a comfortable gray sofa and a coffee table resting on a light rug. Bright windows allow natural light to illuminate the room. A television is positioned on a media console, along with a small dining table and chair set against the wall.

Guest suite in Plymouth

Downtown Plymouth, WI Second Floor 2 Bed Apartment

4.95 out of 5 average rating, 22 reviews

The exterior of a two-story home is displayed, surrounded by a lush green landscape. A stone-lined driveway leads to the entrance, featuring stairs that ascend towards the front door. The home’s siding is a muted green, and a black grill is visible on the upper deck.

Home in Plymouth

Turn 15 Lodge near Road America

5 out of 5 average rating, 24 reviews

The exterior of the property is framed by lush greenery and colorful flowering plants. A rustic wooden fence runs along the foreground, while the house is partially obscured by trees, creating a serene and inviting environment.

Home in Kiel

Kiel River House

5 out of 5 average rating, 22 reviews

An aerial view showcases the cabin nestled among lush greenery, adjacent to a serene lake. A well-maintained path leads from the home to the water's edge, framed by trees reflecting vibrant autumn colors. The peaceful landscape invites relaxation and exploration.

Cabin in Cascade

Lakeside Cabin Retreat Relax at Private Lake House

5 out of 5 average rating, 54 reviews

The exterior of the rustic cabin is framed by lush greenery, showcasing a combination of log and stone construction. A circular stone patio features a wooden bench and a fire pit, inviting gatherings in a tranquil outdoor setting surrounded by nature.

Cabin in Cascade

Rustic Chic Cabin in Kettle Moraine