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Kohler vacation rentals

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Top-rated vacation rentals in Kohler

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Rental unit in Sheboygan

4.97 out of 5 average rating, 139 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!

Cottage in Oostburg

4.97 out of 5 average rating, 261 reviews

Sandalwood Cottage - 300 Feet From Lake Michigan

A HIDEAWAY one mile East of I-43 nestled in beautiful wooded acreage across from Lake Michigan, on a private drive. Just South of Sheboygan. Close by: Whistling Straits & PGA golf courses. Ice Age Trail in the Kettle Moraine, Elkhart Lake - Road America, Charter Fishing, Kohler Andrae State Park, Several State & local beaches, & several 5 star restaurants. 2 hours & 20 min from Chicago. 45 min from Milwaukee, 65 min from Green Bay. Rest, Relax and Unwind in the tranquil setting at Sandalwood.

Home in Sheboygan

4.95 out of 5 average rating, 186 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.

Rental unit in Sheboygan

4.98 out of 5 average rating, 130 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.

Rental unit in Sheboygan

4.92 out of 5 average rating, 456 reviews

Cozy Sheboygan Upper

We began caring for this home and property in 2018, and this 1870's home needed some love. We have been steadily remodeling since we moved in and it's starting to feel pretty great. We're excited to share it and the neighborhood with you. We are two blocks west of North Beach/Deland Park, 4 blocks to the river front boardwalk, home to many restaurants, cafe's, and shops. We are also four quick blocks to downtown which hosts many more restaurants, shops, museums and parks.

Guesthouse in Oostburg

4.91 out of 5 average rating, 305 reviews

Beach House

This guesthouse is detached from the main house and comes with garage parking and has all the amenities you want including a wood-burning fire place! Towels, bath tissue, soaps and travel items. AC Window Unit. Kitchen includes pots/pans, dishes, mugs/glasses, coffee pot, toaster and microwave. Paper goods and hand sanitizer included. New appliances and new water heater in 2020. The beach is steps away with a fire pit, boat house lounge, kayaks, beach toys and bicycles.

Home in Sheboygan

4.94 out of 5 average rating, 189 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.

Home in Sheboygan

4.96 out of 5 average rating, 112 reviews

Good VIBES On the Third COAST- Pets Welcome

Peaceful bohemian retreat with a lively vibe! Perfect for couples, remote workers, girls weekends, golf outings and families! A short walk /bike ride downtown, to the lake or farmer's market. Visit locally owned shops and the world-renowned Kohler Art Museum. Only a 10 minute drive to the famous Whistling Straits/Irish golf course or Kohler Water Spa. Whatever brings you here, we look forward to your visit. Come and enjoy everything Sheboygan has to offer!

Rental unit in Waldo

4.98 out of 5 average rating, 269 reviews

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.

Home in Sheboygan

4.97 out of 5 average rating, 135 reviews

Lake Michigan home with gorgeous views!

Our beautiful lakefront home is perfect for bringing everyone together - Ladies weekend, guys golf trip, family reunion, Packers games...this is your place. Minutes to downtown Sheboygan/Kohler, with 5 star PGA championship golf courses (Black Wolf Run, Whistling Straits, The Bull of Pinehurst), Kohler Waters Spa, and the beaches/dunes of Kohler Andrae State Park. Renovated bedroom and movie room completed early 2020.

Home in Sheboygan

4.97 out of 5 average rating, 128 reviews

Lakeview Beach Bungalow - With outdoor Hot Tub!

Beautifully updated beach house just one block off of Lake Michigan. Beautifully landscaped backyard with pergola and 6 person Hot Tub! Watch the sunrise and sunset from the second floor master balcony. Walk to the lake and enjoy the wind surfers and gorgeous scenery. Close to downtown and major parks. This three bedroom home will impress. Tastefully decorated. First floor laundry. Massive bathroom with deep soaking tub.

Rental unit in Sheboygan

4.84 out of 5 average rating, 291 reviews

Sheboygan Surf House - The Elbow

Located just 24 steps above Wisconsin's first Surf Shop, EOS Surf. Our newly remodeled Urban living oasis is a studio and a half that is conveniently located in the heart of downtown, just steps from renown bars and restaurants and only blocks to Lake Michigan, The Sheboygan River, South Pier and Blue Harbor. Whether you are here for adventure sports like Surfing on the Great Lake or leisure time SSH is perfect for you.

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Popular amenities for Kohler vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near Kohler's top sights

Blackwolf Run Golf Course43 locals recommend

The Blind Horse Restaurant & Winery42 locals recommend

Bookworm Gardens31 locals recommend

Kohler Design Center30 locals recommend

The Horse & Plow26 locals recommend

Kohler Waters Spa at Destination Kohler21 locals recommend

Other great vacation rentals in Kohler

Condo in Sheboygan

4.97 out of 5 average rating, 59 reviews

Urban Townhouse

Earthen home in Elkhart Lake

4.97 out of 5 average rating, 36 reviews

Camp Skywood

Home in Sheboygan

4.97 out of 5 average rating, 30 reviews

4 Bedroom Beachfront Condo

Rental unit in Sheboygan

4.85 out of 5 average rating, 53 reviews

Fully Loaded and Clean! King

Home in Sheboygan

4.98 out of 5 average rating, 53 reviews

The Suncatcher -Steps from Lake - Fenced Yard

Condo in Sheboygan

4.91 out of 5 average rating, 34 reviews

Ellis District Urban Lake Condo

Loft in Sheboygan

4.98 out of 5 average rating, 94 reviews

Spacious/stylish, 2br loft

Cabin in Oostburg

4.93 out of 5 average rating, 98 reviews

HOT TUB, Beach Access near Kohler-Andrae

Quick stats about vacation rentals in Kohler

Total rentals
20 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
1.1K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Kohler?
Yes! Work meets play with ease at over 10 vacation rentals in Kohler featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there family-friendly house rentals in Kohler?
Kohler has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Kohler?
Experience the best of Kohler with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Kohler have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Kohler. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Kohler have wifi?
Absolutely! We offer over 20 house rentals with wifi in Kohler. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Kohler?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

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