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Family-friendly holiday rentals in Waukesha

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Waukesha

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

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Top guest favourite
Yurt in Cambridge
4.98 out of 5 average rating, 250 reviews

YurtSimple

YurtSimple is where life slows down and people unplug. It’s forest bathing in nature. It’s getting away from it all to spend time with a partner, by oneself, and sometimes with pets. You’ll be driving past YurtCation (about 300 feet past YurtCation) to get to YurtSimple. YurtCation is 20’ in diameter and YurtSimple is 16’ in diameter. Wood and charcoal are provided. You may cook on the indoor wood stove top, or visit any number of great restaurants 2 miles away. You can even order pizza delivery

Top guest favourite
A charming red farmhouse is set against a snowy landscape, surrounded by a white fence. Leafless trees create a serene backdrop, enhancing the rural setting. The house features a mix of traditional and modern architecture with snow covering the yard.
Guest house in Richfield
4.95 out of 5 average rating, 296 reviews

Peaceful weekend or extended stay, full amenities

The Country Retreat at the historic Schmitz Family Farm is close to many attractions, ideal for couples, families, girls' weekends, extended stays, business travel, and is dog friendly. Enjoy a sunrise or sunset, get cozy at the fireplace, or indulge in the many activities our area has to offer. We feature two beautiful bedrooms, living room with two sleeper sofas (can also be used as a third bedroom, as door closes for privacy), laundry room, full kitchen, coffee nook, quiet deck and backyard.

Guest favourite
A living room is presented with a gray sofa, a minimalist table, and wooden chairs. Natural light enters through large windows, accentuated by decorative curtains. A patterned area rug covers the floor, while a ceiling fan hangs above, contributing to the room's comfortable ambiance.
Flat in West Allis
4.95 out of 5 average rating, 229 reviews

Sunny State Fair Sojourn!

Newly renovated upper unit in a 1902 Victorian home. 2 bedroom, one bath, kitchen, dining area, living room, and office space! Less than one block from Wisconsin State Fair Park, The Milwaukee Mile and local bus routes! Minutes from American Family Field, Milwaukee County Zoo, and more! Local shuttle to Summerfest and other concerts and sporting events withing walking distance! Private balcony, free parking for one car, private laundry in the unit. Owner occupied lower for over 25 years!

Guest favourite
Home in Waukesha
4.93 out of 5 average rating, 198 reviews

Pet-Friendly Retreat•Sleeps 8•Huge Yard•Fire pit

Wake up to sunrise over a peaceful backyard and enjoy your morning coffee on the private balcony. Evenings are perfect by the fire pit under a starry sky. Just a 5 minute drive from Pewaukee Lake Pet-friendly home with a large yard and fire pit - ideal for relaxing and spending time together. Open-concept living, kitchen, and dining area creates a warm, inviting space to gather. Sleeps up to 8 and is best suited for small families or close-knit groups who prefer a more cozy, intimate layout.

Top guest favourite
A paved driveway winds through a lush wooded area, bordered by greenery and tall trees. The home can be seen nestled in the distance, blending harmoniously with the natural surroundings.
Home in Muskego
4.89 out of 5 average rating, 142 reviews

Muskego Hideaway on 2 Acre Lot

Forget your worries in this beautifully updated 4 bedroom, 2 bath home on a 2 acre wooded hillside. Convenient location with easy access to the Milwaukee airport. Only a minute's drive to Little Muskego Lake and the sandy beach at Idle Isle Park. Easy drives to Alpine Valley, Lake Geneva, and The Rock Sports Complex. Only 2 minutes from I43 for easy access to Milwaukee for Brewers, Bucks, and the many festivals. Relax on the deck or patio and watch the deer and other wildlife in the backyard.

Guest favourite
A spacious living area features a light-colored sofa and a rustic wooden coffee table, complemented by a textured area rug. Large windows, dressed in sheer white curtains, allow natural light to fill the room, which includes a television mounted on the wall.
Home in West Allis
4.94 out of 5 average rating, 103 reviews

The Stallis Palace

Discover modern comfort in this 3BR, 1.5BA gem in central West Allis, WI. Spacious and fully furnished, enjoy craftsman woodwork, modern decór, and an abundance of light flooding through oversize windows. Walk to shops, dining, and nightlife. Within 5 miles of several major regional medicals centers! Master BR with office, porch, and outdoor dining area. Local, experienced hosts, ultra high-speed internet, and smart TVs make this the perfect blend of style and convenience. Book today!

Top guest favourite
A historic stone home is presented, featuring multiple windows that enhance its classic appeal. A well-maintained garden with colorful flowers surrounds the exterior, creating a welcoming entrance to the Butler Place. A sign displaying the property's name is held by two guests in front of the house.
Guest suite in Sussex
4.96 out of 5 average rating, 334 reviews

The Loft @ The Butler Place. 1846 homestead.

The Loft at the Butler Place is a beautiful, quiet retreat set in the rural suburb of Sussex, just 30 minutes west of Milwaukee. The home is the 1846 homestead of the William Butler family, making the home older than the State of Wisconsin! The 2019 remodel of the Loft is in sophisticated farmhouse style and pays tribute to the history of the home in its furnishings, up cycled pieces, and beautiful setting. "Broken becomes blessed" both tells and compells as an invitation to all.

Superhost
Home in West Allis
4.86 out of 5 average rating, 189 reviews

KING BED/Amazing Location/Free parking/Wi-Fi

Enjoy a fun and relaxing stay with family or friends in this stylish, cozy, and comfortable lower unit, which features: 2 bedrooms (1 king, 1 queen ) 1 bathroom Fully equipped kitchen with dining table and designated coffee bar Living room with a 65” smart TV (Netflix included) Home office space Free parking spot Located just a short drive (4 min) from I94, this home offers easy access to all the city's major attractions * the ideal base for exploring the best of Milwaukee

Top guest favourite
Tall sunflowers bloom vibrantly in a garden, displaying bright yellow and orange petals. A wooden gazebo with hanging lights stands in the background, surrounded by lush greenery. Soft sunlight filters through the trees, enhancing the serene outdoor setting.
Guest suite in Sussex
4.99 out of 5 average rating, 153 reviews

Garden Retreat in law Suite

Welcome to our in-law suite apartment featuring a full eat-in kitchen, living room, queen bed in large bedroom, walk in closet and full bathroom with walk-in shower. Our beautiful two acre yard has many areas to relax in, including a hammock and fire pit for the evenings. Twenty mins. to Erin Hills and Holy Hill and a half hour to most downtown Milwaukee attractions, as well as the RNC activities taking place this summer. Lots of city tips and suggestions for our guests.

Top guest favourite
The front view of a rustic stone cabin is framed by lush green trees. The structure features a wooden overhang supported by sturdy columns, with large windows allowing natural light to fill the interior. A neatly stacked pile of firewood is visible at the base.
Cabin in Whitewater
4.95 out of 5 average rating, 369 reviews

Glamping Cabin on Cold SpringTree Farm

Unfortunately we can't accommodate same day bookings as we don't have enough lead time to prep the cabin for your stay. Glamping on a working Christmas tree farm. Beautiful single room stone cabin with loft and wood burning stove. Two small beds in loft and futon on main floor folds out into full bed. Lots of room around to pitch tents as well. Situated on 40 acres of land with a pond, barn with basketball court, creek and Christmas tree fields.

Top guest favourite
A secluded outdoor patio is highlighted by a well-equipped hot tub, surrounded by lush greenery and wooden fencing. Comfortable seating is arranged nearby, with a patterned rug beneath a shaded area. Decorative plants and a charming umbrella enhance the relaxing atmosphere.
Home in Wauwatosa
5 out of 5 average rating, 301 reviews

The Little Gray House

Summer time in the 414! We've got a few small openings left this summer, maybe they work for you? Time to start thinking about booking for fall and winter so you can get in on the best little Airbnb around! All the home upgrades are done, and we'l be posting photos within the next couple of weeks. The Little Gray House has attained rave reviews from travelers around the world for its comfort, cleanliness, and convenience. Happy to have you!

Top guest favourite
A welcoming living area features a dark leather sofa and loveseat, complemented by a wood coffee table atop a plush area rug. Natural light enters through two windows, enhancing the space's warmth. Artwork is displayed on the wall, adding a touch of character.
Flat in West Allis
4.96 out of 5 average rating, 220 reviews

Clean 2 bedroom/1 bath close to everything!

Charming, recently and tastefully furnished 2 bedroom 1 bathroom apartment with private entrance and parking. Close to downtown, shopping malls, zoo, hospital, airport, and main freeways. Full kitchen with stove, microwave, coffee pot, toaster, and kitchenware. Unit has TVs and WiFi. Coin operated laundry is accessible in building. Why stay at a hotel when you can feel at home in this lovely unit?

Popular amenities for Waukesha family-friendly rentals

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Quick stats about holiday rentals that are family-friendly in Waukesha

  • Total holiday rentals

    Explore 20 holiday rentals in Waukesha

  • Nightly prices starting at

    Waukesha holiday rentals start at £30 per night before taxes and fees

  • Verified guest reviews

    Over 700 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Waukesha holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Waukesha rentals

  • 4.6 Average rating

    Waukesha stays receive an average rating of 4.6 out of 5 from guests