Pet-friendly vacation rentals in Sheboygan

4.93 out of 5 average rating, 301 reviews

A rustic modern home is showcased, featuring a spacious wraparound deck surrounded by lush greenery. An inviting hot tub glistens in the sun, and an arcade room with various games is displayed, offering entertainment options for guests.

Home in Elkhart Lake

The LODGE in Elkhart Lake. —-Hot Tub & Arcade—-

Rustic modern home w/ hot tub, arcade & fireplace right on the edge of Elkhart Lake. Road America, great golf, The Ice Age Trail, & the Kettle Moraine are all at your doorstep. This cozy home is 4 blocks from the downtown of Elkhart lake. Yet it still has an acre to explore & enjoy nature. Only 4 miles from Road America. 2 bedroom w/ 2 extra sofa sleepers & 2 baths. Perfect for racers or romantic getaways. The arcade/Pinball room has over 10 games. Perfect base camp. We got your bases covered

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, 169 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 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.

4.95 out of 5 average rating, 101 reviews

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

Renovated 1930's home located in the historic downtown district within walking distance of breathtaking views of Lake Michigan, trails, parks, shopping, dining, Kohler Art Museum, Children's Museum and more! You will enjoy the 1200 square foot, two bedroom renovated upper unit of this historic home. Great care was taken to keep the old world charm. We know you will enjoy our "Blast from the Past" as you play records, tapes, and cd's. Send inquiry on big discounts on stays ore than 2 days!

4.93 out of 5 average rating, 138 reviews

Coastal Comfort Near Lake MI & Downtown

Welcome to the Coastal Comfort! Comfort: noun - a state of physical ease and freedom from pain or constraint Come in and unwind at our coastal 3 bedroom lower unit home near Downtown Sheboygan, Lake Michigan, Whistling Straits and Kohler/Andrae State Park. You can enjoy an evening at home with all your favorite streaming services, or 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.

Superhost

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.

4.83 out of 5 average rating, 229 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

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.

4.91 out of 5 average rating, 119 reviews

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!*

4.96 out of 5 average rating, 185 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.

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, 223 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 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.

4.97 out of 5 average rating, 105 reviews

The Suncatcher -Steps from Lake - Fenced Yard

Welcome to the Suncatcher. Our cozy and bright Midwest retreat just a block away from Lake Michigan . Step into our lovingly remodeled 1930's home where modern comfort meets timeless charm. As you enter you will be greeted by the inviting warmth of exposed brick walls and abundance of natural light that fill every corner. With three bedrooms and two bathrooms, our spacious retreat is perfect for families, friends, or golf enthusiasts seeking a relaxing getaway.

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.

4.85 out of 5 average rating, 267 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

Earth homes in Elkhart Lake

A serene outdoor setting features a stone fire pit surrounded by wooden benches. The custom-built home, with large windows, is visible in the background. Soft twilight hues illuminate the peaceful landscape, complemented by trees lining the property.

Secluded Elkhart Retreat | Pool, Hot Tub & Sunset

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 home. Tap the ❤️ to save this listing!

4.98 out of 5 average rating, 162 reviews

4.95 out of 5 average rating, 165 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

Guest Favorite | Super Host + Clean & Modern Stay!

Unwind in this modern retreat just minutes from Whistling Straits Golf, Road America, Lake Michigan, and year-round outdoor adventures. The bright, open living spaces feature high ceilings, skylights, and stylish furnishings, with thoughtful comforts like heated bathroom floors. Enjoy the spacious outdoor living area for relaxing after a day out. Ideal for golfers, couples, families, wedding groups, business travelers, and traveling nurses.

Popular amenities for Sheboygan pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.96 out of 5 average rating, 347 reviews

Home in Plymouth

Country Cheese Factory - King Bed!

4.99 out of 5 average rating, 235 reviews

Home in Kiel

Red Willow Guest House

The exterior of the home features a charming two-story design with a gabled roof and a welcoming front entrance. Large windows allow natural light to fill the space. A small seating area is visible on the front patio, complemented by greenery and a neatly landscaped yard.

4.9 out of 5 average rating, 68 reviews

The perfect location!

A spacious living area features a comfortable navy blue sectional sofa, complemented by two cushioned chairs. A wooden coffee table sits at the center, while artwork adorns the walls. Soft lighting from multiple chandeliers creates a welcoming environment.

4.99 out of 5 average rating, 93 reviews

Sheboygan's Great Lakes House

An entertainment area is highlighted by a pool table positioned at the center, with natural light streaming through large windows adorned with patterned curtains. Two small chairs are placed against the wall, while a doorway leads to a bathroom in the background.

4.91 out of 5 average rating, 64 reviews

Downtown 4BR-Game Room – 5 Walk to Lake, Pets Ok!

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.

5.0 out of 5 average rating, 38 reviews

Norwind Ranch - Peaceful Retreat Near It All

4.99 out of 5 average rating, 99 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

Lake Michigan Views | 4BR Near Whistling Straits

5.0 out of 5 average rating, 31 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

Hello Pumpkin! Mid-week October Dates available!

Pet-friendly home rentals with a pool

5.0 out of 5 average rating, 8 reviews

Home in Elkhart Lake

Lake Views | Walk Everywhere | 3BR Beach Resort

Condo in Elkhart Lake

Hart & Sol on Elkhart Lake

5.0 out of 5 average rating, 3 reviews

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.

Resort Condo on Elkhart Lake

5.0 out of 5 average rating, 14 reviews

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.

Hotel room in Elkhart Lake

Resort Life 2 Queen Suite

4.8 out of 5 average rating, 10 reviews

Private, pet-friendly home rentals

4.85 out of 5 average rating, 121 reviews

The exterior of a spacious lakeside home is showcased, featuring large windows and a welcoming porch. A green lawn extends towards the water, accompanied by bright blue kayaks and a swing set. A tall tree provides shade, enhancing the outdoor ambiance.

Cottage in Random Lake

Private 3 bedroom lake house

4.97 out of 5 average rating, 127 reviews

The cabin stands amidst lush greenery with a gently sloping lawn leading to a stone pathway. The modern exterior features large windows and a spacious upper deck surrounded by trees, providing a serene lakeside retreat.

Chalet in Campbellsport

Long Lake Chalet

5.0 out of 5 average rating, 101 reviews

Apartment in Kewaskum

Local Landmark KL / Artisan Coffeehouse

4.94 out of 5 average rating, 35 reviews

Historic Lower Unit Near Downtown, King/Queen Beds

5.0 out of 5 average rating, 90 reviews

A comfortable living room features two sofas and an armchair arranged around a central coffee table. Natural light enters through a large window, casting a warm glow on the softly colored walls. A television and table lamps are positioned for convenience.

Barn in Sheboygan

Character filled 3 Bedroom Carriage House

5.0 out of 5 average rating, 11 reviews

Boat House | Lower Unit, Walk to Beach & Downtown

A light-filled living space is furnished with a comfortable blue sofa and armchair. A round coffee table sits atop a soft area rug, while a large TV is positioned on a wooden media console. Natural light filters through the window, complemented by a potted plant.

4.9 out of 5 average rating, 88 reviews

Beautiful & Convenient!