
Family-friendly holiday rentals in Kohler
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Top-rated family-friendly rentals in Kohler
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Fernwood Elkhart Lakefront: hot tub, pier, kayaks
Beautiful, serene lakehome on pristine Elkhart Lake. The hot tub, deck, screen porch & stone patio all have gorgeous lake views. The private pier is perfect for a dip, paddling or lounging by the water before basking in a luxurious sunset soak in the hot tub. Enjoy a stroll into the adorable town of Elkhart via the rustic lakefront path. With a chef’s kitchen and extensive amenities, it's perfect for a weekend or extended stay year round! We strive to be inclusive and welcoming 🏳️⚧️BLM🏳️🌈

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.

The Hemingway on Church - It Tolls For Thee
"Kristine's property has all the charm of a modern day Mayberry" -Michael This 1906 historic home is nestled in the heart of the equally historic "Village of Kohler." Completely remodeled in 2019 adding Kohler spa amenities and modern touches to its original charm. Mixing modern & antique furniture finds like the Hemingway Sideboard (which inspired the literary theme) make this historic hideaway a true Kohler destination. "You cannot get a better location in Kohler than this house!" -Dennis

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.

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.

Luxury Retreat Near Kohler | Hot Tub + Arcade
Hot tub under the stars, private theater, and a full arcade—set on 4 wooded acres just minutes from Whistling Straits & Blackwolf Run. Hosted by Wisconsin Getaways—known for high-end homes and exceptional guest experiences. ✔ Hot tub overlooking the river ✔ Private theater w/ surround sound ✔ Full arcade: Golden Tee, skee-ball + air hockey ✔ Fire pit + gazebo for late nights ✔ 10–20 mins to Kohler golf & Lake Michigan Perfect for golf trips, families, and group getaways. Book early.

sauna and hot tub on 5 private acres
Looking for a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your getaway awaits!

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.

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.

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.

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 home. Tap the ❤️ to save this listing!

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!
Popular amenities for Kohler family-friendly rentals
Family-friendly home rentals with a hot tub

Spacious Home - 4 BR/2.5 Bath + Hot Tub + Game Rm

Oma's Beach House

Family lake retreat w/ hot tub! Amazing sunsets!

HOT TUB~KingBed~PoolTable~PokerTable-BatmanMovieRM

The Woods Estate walk to RoadAmerica modern luxury

Log Cabin At The Lake

Road America Oasis: 25 Acres, Hot Tub & Orchard

Paddock Point Lakehouse. Road America+Hot Tub
Family- and pet-friendly home rentals

The Blue Cobb House

Quiet Country Charm

Long Lake Chalet

Local Landmark CF / Coffeehouse / Kettle Moraine

Country Guest House - Beautiful Gardens!

Family Cottage, Walk to the lake (pet friendly)

Inn on Billy Goat Hill

*Front porch, fenced in backyard- PetsWelcome*
Family-friendly home rentals with a pool

Breezy Acre...Relaxing small family get a way.

Lake Views | Walk Everywhere | 3BR Beach Resort

The Little Palm in Elkhart Lake!

Walkable Lake Escape! Elkhart Lake Condo

Road America Retreat- Hot Tub+Heated Pool-4BR Home

Luxury Pool Retreat-2 Acres-Near Whistling Straits

Resort Life 2 Queen Suite

Resort Condo on Elkhart Lake
Quick stats about holiday rentals that are family-friendly in Kohler

Total holiday rentals
Explore 10 holiday rentals in Kohler

Nightly prices starting at
Kohler holiday rentals start at $141 SGD per night before taxes and fees

Verified guest reviews
Over 870 verified reviews to help you choose

Wifi availability
10 of Kohler holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Kohler rentals

4.9 Average rating
Kohler stays are highly rated by guests – averaging 4.9 out of 5!
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- Kohler-Andrae State Park
- Whistling Straits Golf Course
- Baird Center
- Milwaukee Public Museum
- Bradford Beach
- Discovery World
- Riverside Theater
- Blackwolf Run Golf Course
- Marquette University
- Fiserv Forum
- Pabst Mansion
- Betty Brinn Children's Museum
- Paine Art Center And Gardens
- American Family Insurance Amphitheater
- Fox Cities Performing Arts Center
- Holy Hill National Shrine of Mary
- Atwater Park
- Eaa Aviation Museum
- Mitchell Park Horticultural Conservatory
- Lake Park
- Road America
- Marcus Center for Performing Arts
- Neshotah Park
- Wisconsin Maritime Museum





