
Family-friendly holiday rentals in Plymouth
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Plymouth

Total holiday rentals
Explore 40 holiday rentals in Plymouth

Nightly prices starting at
Plymouth holiday rentals start at $102 NZD per night before taxes and fees

Verified guest reviews
Over 2,240 verified reviews to help you choose

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Plymouth holiday rentals include Wi-Fi access

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

4.9 Average rating
Plymouth stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated family-friendly rentals in Plymouth
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

The 2400 sq ft Plymouth Paddock near Road America!
This charming two story, 2400 square ft colonial house is the perfect respite for families looking to connect, or race fans looking for a home during race weekend. Only 4 miles from Road America the location is close to all of Sheboygan County's finest attractions. Located two blocks from downtown on a quiet street, its up to you how you want to spend your evening. You could walk downtown for a bite, have a campfire, make a meal, or just spend time together. Welcome to your home away from home!

Elkhart A-Frame, Wooded Retreat near Road America
The Elkhart A-Frame is an ideal location for the adventure seeker who wants a unique and private experience that is still close to all the action. The home sits on a wooded three-acre private retreat only about a mile from the village of Elkhart Lake, Road America, and Golf Courses. This unique cabin was built in the 1970's but has been recently renovated with a fun Scandinavian modern flair. It has all the amenities for a memorable vacation stay that provides plenty of epic photo opportunities.

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

Woodside Cottage Guest House-Close to Road America
Woodside Cottage in the Kettle Moraine forest of East Central Wisconsin offers a quiet private getaway for Road American race fans, golfers or those wanting just to have a break from the city and explore the area. This 2 bedroom guesthouse can host 8, with laundry, full kitchen, living room and outdoor fire pit. Due to family guest allergies, we are pet free. Located 4 miles from gate 4 at Road America and 20 miles from Whistling Straits golf course. WIFI available, but unreliable. 3 cars MAX

The Loft at Hickory Haven-A Modern Rural Studio
The Loft at Hickory Haven is a modern country retreat made for two! Mary & Bob constructed The Loft studio in 2020 and filled it with the modern traveler's amenity wish list: A comfy king bed, central AC, a gas-fired stove, a modern bathroom, and a kitchenette with dining area. The property's rural setting offers a peaceful haven from your daily grind. Your day will start with the chirping of birds or a wild turkey sighting and end with a star-filled sky that is a site to behold! Welcome!

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

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.

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.

hot tub and sauna 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!

Private 3 bedroom lake house
A beautiful spacious 3 bedroom with sofa bed (sleeps 9 guests) with lake access just steps away from the backyard. Includes washer and dryer, all cooking amenities and a grill, 3 TVs with cable (including Netflix and Disney+ capabilities), a two person canoe n 3 kayaks, hammock, board games, and books for leisure reading. Fish off the private peer. Light the bonfire in the fire pit (firewood included) by the patio onlooking the lake. Pets are allowed with a $200 pet fee.

Cottage on Lake Winnebago
Furnished Cottage on Lake Winnebago with beautiful sunrises. 1 bedroom with queen bed. There is plenty of space for air mattresses in common areas. 1 queen air mattress available. One bath, full kitchen fully stocked with dining area, bring your own food to prepare. Bring your water toys or boat, launch nearby and dock access in warmer months with great fishing. Winter months, bring your snowmobile, trails nearby. Great ice fishing when lake is frozen and ice is safe.

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.
Popular amenities for Plymouth family-friendly rentals
Family-friendly home rentals with a hot tub

Boutique Wellness Retreat - Hot Tub and Fireplace

Fernwood Elkhart Lakefront: hot tub, pier, kayaks

State Park A-Frame: Hot Tub, Arcade & Hiking

Woltring Waters Waterfront Home + Hot Tub

HOT TUB~KingBed~PoolTable~PokerTable-BatmanMovieRM

Luxury Retreat Near Kohler | Hot Tub + Arcade

Road America Oasis: 25 Acres, Hot Tub & Orchard

Oma's Beach House
Family- and pet-friendly home rentals

Local Landmark CF / Artisan Coffeehouse

Quiet Country Charm

Lovely modern two bedroom home with fire pit

Carriage House Sheboygan, Lake Mich beach access!

Guest Favorite | Super Host + Clean & Modern Stay!

Sheboygan Surf House - Jetties

Long Lake Chalet

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

The Lake Street Kickback in Elkhart Lake!

Road America Retreat-4 BDRM-2BA-Hot Tub+Pool

Lake Views | Walk Everywhere | 3BR Beach Resort

Newly Renovated -Oshkosh Home on Lake Winnebago

Private Beach, Pools & Full-Kitchen

Lakefront Condo, Private Beach/Pool, Walk to Town

VicVill | WaterViews | Vintage Charm Meets Comfort

Wooded Retreat w/ Hot Tub & Private Beach
Destinations to explore
- Chicago Holiday rentals
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- Kohler-Andrae State Park
- Whistling Straits Golf Course
- Baird Center
- Milwaukee County Zoo
- Marquette University
- Riverside Theater
- Eaa Aviation Museum
- Bradford Beach
- Pabst Mansion
- Blackwolf Run Golf Course
- Fiserv Forum
- Holy Hill National Shrine of Mary
- Mitchell Park Horticultural Conservatory
- Discovery World
- Atwater Park
- Paine Art Center And Gardens
- Fox Cities Performing Arts Center
- Lake Park
- Little Switzerland Ski Area
- Lion's Den Gorge Nature Preserve
- The Bull at Pinehurst Farms Golf Course
- Deland Park
- Neshotah Park
- Vines & Rushes Winery





