We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Family-friendly vacation rentals in Plymouth

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Plymouth

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Top guest favorite

The two-story home features a beige exterior with multiple windows, surrounded by a grassy yard. Two chairs are positioned in front on a small patio area. Large trees provide shade, while a view of the countryside and other structures is visible in the background.

Home in Glenbeulah

4.98 out of 5 average rating, 130 reviews

Stay at Sunrise LLC, Like being at Grandma's

Welcome to Stay at Sunrise LLC. We offer a clean and comfortable home for your vacation enjoyment. We are in a rural area, recreation trail head is 3 miles east of us as is the Wade House, 7 miles from Road America. Large yard, Fire pit, picnic table, child swing set. Garage parking on site if arranged in advance. We do not have WIFI Phone reception for Internet is good. No Cable or Satellite TV, Over 32 antenna channels. Smoking is allowed outside of the home. No pets allowed.

A red cottage is nestled among lush green trees, with a winding driveway leading to its entrance. Steps ascend to the upper level, and patches of sunlight filter through the leaves, highlighting the natural surroundings.

Guesthouse in Plymouth

4.97 out of 5 average rating, 119 reviews

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

Top guest favorite

The front exterior of the duplex showcases a charming farmhouse style with light grey siding and white trim. Two levels of porches with railings are complemented by doorways in vibrant turquoise. Flower baskets hang from the porch beams, and a garden with greenery enhances the inviting atmosphere.

Apartment in Port Washington

5 out of 5 average rating, 239 reviews

Beautiful Port home short walk to town and lake

Enjoy Grace Guest house and the sights and sounds of Port Washington at our bright turn of the century duplex. Your private upstairs unit has 1.5 baths, a full kitchen and 3 bedrooms. Freshly renovated, our 1890 home is sure to charm with its many original features and large modern bathrooms and kitchen. Your second floor private walk-out deck is a great place to enjoy a morning coffee or cocktail and take in the Lake View. Port Washington’s shops and restaurants are a quick 4 minute walk.

Top guest favorite

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

4.95 out of 5 average rating, 146 reviews

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).

A tranquil view of Lake Michigan at sunset, where calm waters reflect soft hues of orange and pink. The sky showcases wispy clouds, and a distant bird is seen soaring above the serene landscape, creating a peaceful setting.

Home in Sheboygan

4.94 out of 5 average rating, 200 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.

A warm living area features exposed log walls and a stone fireplace. Comfortable leather seating is arranged around a coffee table. A television sits on an entertainment unit, and framed photographs decorate the mantle. Natural light enters through windows near the ceiling.

Cabin in Campbellsport

4.98 out of 5 average rating, 145 reviews

Log Cabin Luxury on a Lake

Enjoy a 1,400 sq.ft. home in the Northern Unit of the Kettle Moraine Forest on 50' of shore. Enjoy the lake for swimming, kayaking, fishing, and floating! Lots of trails for hiking nearby and other fun summer activities! Updated home with a log cabin feel. Modern kitchen and great room—perfect for game night or sitting by the fireplace. Lake views from the master bedroom and sun room. Beautiful bathroom with big walk in shower. Come see for yourself!

Top guest favorite

A relaxing living area features a stone fireplace as its focal point. Comfortable seating options, including a leather chair and a spacious sofa, are arranged around a rustic coffee table. Large windows allow natural light to fill the space, with glimpses of the surrounding scenery.

Cottage in Fond du Lac

4.99 out of 5 average rating, 287 reviews

Beautiful Lake Home.

Our Beautiful two bedroom cottage is located on the shores of Lake Winnebago . Centrally located to many of Wisconsin's best attractions. Less than 1 hour from Milwaukee, Madison, Green Bay, Close to Oshkosh (EAA) and Elkhart Lake. Includes 2 bedrooms, with plush queen beds, 1 full bathroom, Laundry room with washer and dryer. The perfect home for a laid back group of friends, couples or a family to stay with all the comforts of being at home.

Top guest favorite

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

4.98 out of 5 average rating, 279 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.

Top guest favorite

A warm and inviting bedroom is framed by sliding barn doors, revealing a spacious bed with white bedding. Two bedside tables, each adorned with a lamp, provide light. Natural light enters through two windows, accentuated by wooden trim and classic blinds.

Apartment in Kohler

4.99 out of 5 average rating, 141 reviews

Washington Walk Historic House w/elegant spa bath

This 1880's Historic Riverside Tavern was completely remodeled in 2017, maintaining as much of the original character as possible. The Village of Kohler moved the building to its' current location in 1908 - eventually closing the tavern to establish the Kohler Women's Club in the 1920s. It opened with a tea room on the first floor as well as the upstairs being home to the original Kohler Girl Scouts.

The living area features warm wooden walls and a rustic charm. Natural light filters through large windows and skylights, illuminating a cozy seating arrangement. A small wood stove stands near a patterned area rug, while musical instruments are positioned around the space, enhancing its inviting atmosphere.

Cabin in Hubertus

4.96 out of 5 average rating, 540 reviews

Hugel Hutte - Log Cabin Getaway

Welcome to the Hugel Hutte! This cute little cabin is perched on the hill top. It's feels like a tree house! You have the kitchen to use, but the famous Fox & Hound's restaurant is just steps away. It's literally right next door. So grab a few drinks and dinner...and walk home to your cabin retreat for the night. Enjoy the tranquil naturescape surrounding the house.

Top guest favorite

A comfortable leather sofa with patterned cushions is positioned in the living area. A wooden cabinet with glass doors displays decorative items. The room features a colorful area rug and walls that are partially adorned with wooden accents, contributing to a cozy ambiance.

Apartment in Port Washington

4.93 out of 5 average rating, 300 reviews

Homeport

The apartment is a remodeled former "Summer Kitchen" in the lower level of our cream city brick home. We are located in the heart of downtown next to the marina, close to parks, steps away from restaurants, coffee shops & bars. Lake Michigan is just outside the door! We invite couples, solo adventurers, and business travelers for short and long-term stays.

The exterior of a modern architectural home is illuminated against a twilight sky. Surrounding trees are visible, and outdoor seating is arranged along a spacious porch, inviting relaxation in a serene setting.

Home in Two Rivers

4.94 out of 5 average rating, 362 reviews

Still Bend/Frank Lloyd Wright's Schwartz House

Featured on Netflix's THE WORLDS MOST AMAZING VACATION RENTALS Season 2, ep. 1. Still Bend/Bernard Schwartz House is Frank Lloyd Wright's built version of his Life Magazine "Dream House" design from 1938. The house is located on the East Twin River about a mile from Lake Michigan.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Plymouth family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Three wooden Adirondack chairs are positioned on a dock, facing a serene lake at sunset. A person is visible kayaking in the distance, with mountains silhouetted against the colorful sky.

Home in Plymouth

4.92 out of 5 average rating, 13 reviews

the getaway at crystal lake!

A fully equipped kitchen features wooden cabinetry and a white refrigerator. A white stove and microwave are positioned on the counter, with a red towel hanging from the oven handle. The floor showcases dark, textured tiles that complement the warm wood tones.

Home in Oshkosh

Entire EAA house

A well-maintained wooden deck features a circular fountain at its center, surrounded by vibrant flowering plants and shrubs. Visible are steps leading up from the deck area to a cozy retreat. The scene is framed by lush trees, creating a serene outdoor environment.

Home in Two Rivers

4.96 out of 5 average rating, 93 reviews

Artisan getaway biking, hiking, hot tub, 3 bedroom

The tranquil shoreline of Lake Winnebago is depicted at sunset, with calm waters reflecting soft pastel colors. A sandy beach area is visible, complemented by a cluster of rocks and lush greenery. A wooden bench is positioned nearby, inviting moments of relaxation.

Cottage in Neenah

4.94 out of 5 average rating, 481 reviews

Lake Life, year round hot tub!

Family- and pet-friendly home rentals

A lush green lawn is complemented by two lounge chairs facing a serene lake. Surrounding the area are potted plants and garden furniture, including tables and chairs, set against a backdrop of trees and blue skies with scattered clouds.

Cottage in Manitowoc

4.88 out of 5 average rating, 130 reviews

Year Round Home on English Lake in Manitowoc Cty

Top guest favorite

A charming red farmhouse is set against a colorful sky at sunset, surrounded by a picturesque yard filled with wildflowers. The property features a wooden fence and mature trees, contributing to a serene rural atmosphere.

Guesthouse in Richfield

4.94 out of 5 average rating, 257 reviews

Peaceful weekend or extended stay, full amenities

The exterior view of the home presents a combination of stone and wood siding, accentuated by large windows that showcase the scenic surroundings. A pathway of stepping stones leads to a covered porch, framed by well-maintained grass and nearby trees.

Home in Plymouth

4.76 out of 5 average rating, 21 reviews

Summit Ranch - Elkhart Lake/Road America- 3 mins

An outdoor fire pit area is surrounded by vibrant red chairs arranged in a circle. The sun sets over Lake Michigan, casting a warm glow on the grassy landscape, which gently slopes towards the beach. Additional seating is visible nearby.

Home in Sheboygan

4.94 out of 5 average rating, 51 reviews

3-bdrm beachfront home on Lake Mich, Sheboygan WI

A spacious backyard is displayed, featuring a grassy area surrounded by lush greenery and flowering plants. A stone circle encases a fire pit, while soft lighting from garden fixtures illuminates the path. Mature trees provide shade, contributing to a private and relaxing outdoor setting.

Home in Two Rivers

4.96 out of 5 average rating, 96 reviews

Neshotah Beach Getaway

A welcoming entrance is framed by lush green shrubs and large trees. A set of steps leads to a light blue front door, which is centered within a white-paneled facade. The pathway is bordered by neatly manicured grass, adding to the inviting appearance.

Home in Manitowoc

4.63 out of 5 average rating, 182 reviews

The Blue Door

A modern kitchen is featured with white cabinetry and granite countertops, illuminated by recessed lighting. Stainless steel appliances, including a refrigerator and a double sink, are present. The open layout connects smoothly to the dining area, enhancing accessibility for gatherings.

4.92 out of 5 average rating, 62 reviews

Mequon Wedding Retreat

Four decorative black bottles are arranged on a wooden surface, featuring various embellishments. Two bottles are adorned with twine, while a floral accent and wooden letters spelling 'h' and 'e' are attached to the others, creating a warm, welcoming display.

Home in Oshkosh

4.73 out of 5 average rating, 33 reviews

1 Bdrm Private Home for Rent

Family-friendly home rentals with Wifi

Guest suite in Plymouth

4.9 out of 5 average rating, 51 reviews

Settlement Suite

Top guest favorite

A spacious three-bedroom home is set amidst lush green grass, illuminated warmly by lights from the windows. A gravel driveway leads to an attached garage, surrounded by trees and natural landscaping in a serene rural setting.

Home in Elkhart Lake

4.93 out of 5 average rating, 31 reviews

Aspen House - peaceful & private country home

A sandy beach scene captures a child walking away from a detailed sandcastle, which features tall towers and a round structure on top. The calm waters of Lake Michigan stretch into the background under a clear blue sky.

Home in Two Rivers

4.68 out of 5 average rating, 384 reviews

1 block to Beach- Beach house-Firepit and bikes!

The inviting living area features a plush sofa with a tropical print and a comfortable armchair. A wooden coffee table centers the space, with a view of the kitchen visible in the background. Natural light filters through large windows, illuminating the wooden ceiling and floor.

Home in Oshkosh

4.86 out of 5 average rating, 80 reviews

Shorehaven Lakehouse

Top guest favorite

The modern kitchen showcases rich wooden cabinetry and a large island with granite countertops. A dining table is conveniently set for four, and eight chairs are positioned at the island. Warm lighting from pendant fixtures creates an inviting space, complemented by natural wood flooring.

Apartment in Elkhart Lake

4.99 out of 5 average rating, 71 reviews

Downtown Elkhart Lake - The Quintessential Suite

A serene view of Lake Michigan is framed by a window, showcasing sparkling water reflecting sunlight. A sandy beach is visible in the foreground, along with gentle waves lapping at the shore. Lush greenery is positioned near the window, adding to the natural setting.

Home in Oostburg

4.93 out of 5 average rating, 40 reviews

260 Feet of Sandy Lake Michigan Beachfront

Top guest favorite

A spacious guest home is set against a backdrop of tall trees, positioned near a sandy beach. The exterior features a covered porch and two lounge chairs, inviting relaxation while enjoying the serene landscape.

Home in Oostburg

4.96 out of 5 average rating, 191 reviews

Shamba on the Lake, Oostburg, WI

The image captures a tranquil lake at sunset, featuring smooth water reflecting shades of orange, pink, and purple. Soft clouds drift across the sky, while silhouettes of trees can be seen along the shoreline, enhancing the serene landscape.

Home in Hubertus

4.97 out of 5 average rating, 77 reviews

Lovely Lake property adjacent to GlacierHills Park

Quick stats about vacation rentals that are family-friendly in Plymouth

Total rentals
30 properties
Nightly prices starting at
G$12,539 GYD before taxes and fees
Total number of reviews
1.9K reviews
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool

Destinations to explore