Family-friendly vacation rentals in Pleasant Prairie

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Pleasant Prairie

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

A cozy seating area is presented with two sofas adorned with decorative pillows. A large lamp with a blue shade complements the space, while light filters through the large windows, enhancing the bright atmosphere. A piece of wall art and natural accents are also visible.

Home in Castle Manor

4.93 out of 5 average rating, 104 reviews

Center Lake View Cottage, near Camp&Silver Lakes

Relax & enjoy your stay in this peaceful home in quiet, friendly neighborhood. Launch your boat in Center Lake at end of street or visit one of many lakes nearby. Camp Lake less than 2 minutes away, close to Silver Lake and others. This home has an awesome sled hill, fire pit with seating area, and a relaxing deck with lake views. Close to Wilmot Mountain, Lake Geneva, & Bristol Renaissance Faire. 25 mins to Six Flags or Lake Geneva, 1 hr to Chgo or Milwaukee. 35 mins to Great Lakes Naval Base

Top guest favorite

Guest suite in Zion

4.9 out of 5 average rating, 218 reviews

Non-smoking, attached mother-in-law suite.

25 minutes away from the Naval Station 5 minutes away from the beach. 10 minutes to Wisconsin. 1 hour 40 minutes to O’Hare Airport and downtown Chicago. 40 minutes to Milwaukee Airport 25 minutes to Six Flags and Great Wolf Lodge. Safe and quiet neighborhood with plenty of wildlife right in the back yard. This Mother in Law suite has tons of natural light. For nature lover’s this unit is close to the beach and there are walking trails nearby. Small children maybe heard from 7AM to 7PM.

Top guest favorite

An outdoor deck is furnished with a dining table surrounded by four cushioned chairs. A vase filled with fresh flowers is centered on the table. Soft lighting from hanging bulbs adds a cozy ambiance, with views of the neighborhood skyline in the background.

Apartment in Kenosha

4.99 out of 5 average rating, 189 reviews

Downtown-Treetop Deck-2Bd/2Bth

Discover this one-of-a-kind, shabby-chic second-floor apartment in the heart of Downtown Kenosha — just steps from coffee shops, restaurants, museums, and the shores of Lake Michigan. Ideal for travelers who want everything within walking distance. Relax and unwind on the spacious, completely private back deck — your own hidden oasis tucked among treetops and historic neighborhood buildings. Perfect for stays up to four guests. Please note: This property is not suitable for young children.

Superhost

A stylish living area showcases a red accent chair paired with a marble-top coffee table. The open kitchen features modern appliances, including a refrigerator and oven. Bright cabinetry complements the light-toned wood floor, while a small dining area with two stools is situated near the kitchen.

Apartment in Racine

4.87 out of 5 average rating, 157 reviews

The Greyhound Apartment

Welcome to The Greyhound, an urban oasis in Downtown Racine. Explore monthly events, dine at local hotspots, or visit cultural landmarks like SC Johnson Frank Lloyd Wright building, Racine Zoo, and more. This professionally designed, newly refurbished apartment features a comfy queen bed, queen sofa sleeper, smart TVs (you can stream from your own accounts) a fully equipped kitchen, and laundry. Bring your canine companion (no cat). Nearby, discover The Graduate Apt for larger groups. Enjoy!

Superhost

A spacious living area is furnished with a light-colored sofa, a coffee table, and a single bed draped in a patterned bedspread. Natural light filters through window blinds, illuminating the room. An air conditioning unit is positioned near the entrance, and a ceiling fan sits in the corner.

Tiny home in Beach Park

4.84 out of 5 average rating, 116 reviews

Tiny home in not so tiny Yard

The house has a Queen bed, a Single bed and a sofa. A tiny home in a peaceful neighborhood. Built on 4 city lots, it has plenty of space and privacy. For families visiting the Naval Academy, we are close enough, yet give you space and privacy. Away from the hustle of North Chicago and Waukegan. Nearby attractions are: Naval Base - 11 miles, 20 minutes Six Flags - 7 miles, 15 minutes Illinois State Beach - 2 miles, 5 minutes Chicago - 46 miles, 60 minutes Milwaukee - 50 miles, 55 minutes

Top guest favorite

An open living area is presented with a large sectional sofa and hardwood flooring. The kitchen features stainless steel appliances and a breakfast bar. A dining table with seating and wall shelves adorned with decorative items are visible in the background, contributing to a warm, inviting space.

Home in Beach Park

4.96 out of 5 average rating, 313 reviews

"Magnolia Farmhouse" inspired 4-bedroom home

Enjoy a spacious, open floor plan on a quiet, dead-end street! This "Magnolia Farmhouse" inspired 4-bedroom ranch home is set on one acre. Located 50 miles from Milwaukee, 45 miles from Chicago, and 2 miles from having your toes in the sand at Lake Michigan! Minutes away for the Great Lakes Naval Station (9mi) and the Cancer Treatment Center of America, Six Flags Great America, Gurnee Mills, and Great Wolf Lodge. Whatever brings you here, make Boyce Lane your home away from home today!

Superhost

A cozy living area features two windows dressed with light curtains, allowing natural light to fill the room. A dark sofa is paired with a textured rug on the floor. A small desk with a chair provides a dedicated workspace, accompanied by decorative shelves and a potted plant.

Apartment in Waukegan

4.79 out of 5 average rating, 145 reviews

Cozy Corner, stylish 1bed near Navy Base!

Kick back and relax in this calm, stylish space. This is a newly remodeled 1 bedroom apartment. The Cozy Corner is designed to be a place of peace, for rest and relaxation. Feel right at home in this beautiful apartment. The kitchen is stocked with plenty of utensils and cookware for your favorite meal. Be sure to relax by the indoor fireplace and watch your favorite movies. Dedicated work space with desk and fast wifi perfect for traveling professionals. Longer stays discounted!

Guest favorite

A kitchen area features neutral-colored cabinetry and a round glass dining table set for four. A small floral centerpiece adorns the table, alongside plates and mugs. Appliances include a microwave, stove, and refrigerator, with a coffee maker positioned on the countertop.

Apartment in Kenosha

4.96 out of 5 average rating, 188 reviews

Kenosha! Here for work or play enjoy your stay!

Soft towels, fluffy pillows, complimentary breakfast, soft drinks, and more in a safe and secure environment. Only children over 13 allowed and must be accompanied by an adult. This n-smoking, pet-free 1-bedroom w/queen bed, twin mattress daybed and cot, furnished kitchen and bath apartment is on the 2nd floor of an office building. Free HI-SPD Wi-Fi and big screen Smart TV. Access to museums, universities, shopping, Chicago’s METRO train and only 37 miles from downtown Milwaukee!

Top guest favorite

A serene living area features a large sliding glass door leading to a deck with unobstructed views of Round Lake. Natural wood accents adorn the wall, while a plush sofa and a small coffee table create a relaxing seating space.

Home in Round Lake Beach

4.99 out of 5 average rating, 163 reviews

Round Lake Getaway Retreat

Looking for a calming, peaceful lakeside getaway for you and your loved one? Come stay at our remodeled retreat with private waterfront access to Round Lake. Enjoy peace and reflection meditating on the spirited lake waters rolling into shore. Wake up to inspirational lake views with soul warming coffee, tea or cocoa. Savor deep or lazy conversation with your loved one, surrounded by dreamy décor and captivating nature. Come and relax, restore, and rejuvenate by the lake!

Guest favorite

A rustic cabin with dark wooden logs is situated among tall green trees. The spacious porch features a railing and several chairs, inviting relaxation. Sunlight casts warm tones across the facade, while the surrounding grass and woods enhance the cabin's natural setting.

Guesthouse in Racine

4.9 out of 5 average rating, 241 reviews

Charming log cabin in the woods

This log cabin is an old hunting lodge. It is rustic, charming and quaint, nestled in the woods of Wisconsin and next to a tranquil pond. The location is close to the Johnson Park golf course and 5 miles from the beautiful Lake Michigan shore. It is a perfect place to relax, write or escape from the stress of life. In the winter a 4-wheel drive vehicle is necessary to reach the site. Please note: bathroom facilities are a close walk away. Heating from wood stove only.

Guest favorite

A cozy, well-lit living area is visible, featuring a sectional couch and a decorative rug. A small dining table with wooden chairs is positioned near the kitchen, which is subtly accented with shelves displaying glassware. Windows allow natural light to brighten the space.

Home in Kenosha

4.94 out of 5 average rating, 251 reviews

Lovely home near the beach in a safe neighborhood

Our simple, yet welcoming property is minutes away from beaches, downtown, minor league baseball, the farmers market, and many delicious restaurants, as well as having close proximity to Carthage College, 6 Flags, and a quiet 30 min drive to Great Lakes Naval Base. We are located in the Allendale neighborhood boasting a family-friendly atmosphere on a quiet street. Whether you are here to relax, have fun, or attend special events, our house can provide.

Guest favorite

A spacious and comfortable living area is showcased, featuring a large sectional sofa with decorative pillows and a cozy throw. A coffee table, holding magazines and a candle, complements the soft brown carpet. The kitchenette area, equipped with a full-sized refrigerator, is visible in the background.

Apartment in Winthrop Harbor

4.94 out of 5 average rating, 310 reviews

warm, cozy, spacious, comfortable; special.

Large, Cozy, suite w sweet kitchenette for “portable” meals; full-size refrigerator/ freezer; a writing desk for work. Many little ( in case you forgot) items to keep you comfy. This is a quiet town on the gorgeous Lake Michigan. Near: 6 Flags, Great Lakes Navy Base; Cancer Treatment Centers of America & the city Chicago via the Metra in town. Convenient & Quiet. I have 3 dogs. They are kind, outgoing and will want to meet you.