Family-friendly vacation rentals in Waukesha

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.

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!

In the Canopy (beautiful Brookfield/Milwaukee)

Relax “in the Canopy” of beautiful maples! If you’re looking for party central…this isn’t it. But if you want a comfortable place in a tree-filled neighborhood, just a few minutes from all the best Milwaukee has to offer, you’re in luck! Perfect location for quick access to the city—or to Lake Country to the west. Quiet, comfortable, safe, surrounded by beautiful gardens. We’re in a perfect launching spot to visit Summerfest, Brewers/Bucks games, or Milwaukee's western suburbs. Bring the kids!

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.

The Cozy Coop | Private Upstairs Retreat | Sleep 8

Wake up to sunrise over a peaceful backyard and enjoy your morning coffee off the balcony. Evenings are perfect by the fire pit under a starry sky. Just 5 minutes from Pewaukee Lake This private upper level comes with a large fenced in yard - 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.

West Allis Oasis

Welcome to our cozy 2-bedroom, 1-bathroom home on a quiet street in a fantastic neighborhood. Dog-friendly and perfect for families or solo travelers, enjoy easy access to I-94 and the State Fair Park just a few blocks away. Our home offers a peaceful retreat with comfortable furnishings, a fully equipped kitchen, cozy bedrooms, and large fenced in yard. Relax and unwind in a tranquil environment after a day of exploring. Book your stay today for the perfect blend of comfort and convenience!

Wisconsin Treehouse Getaway!

Featured in Timeout Magazine as Chicago's Top 10 Airbnbs, and in other outlets as Wisconsin's most romantic and top 5 Airbnbs, this space has an immersive nature experience, overlooking a creek and woods with all modern comforts. Imagine yourself in a cabin in the woods to unplug and recharge, waking up to chirping birds as if in a Treehouse! 3 miles to Lake Michigan & dwntn. lf we're home, a complimentary Chai! Come, make lifelong memories at Racine's Best Kept Secret No local bookings.

Nice 1 BR Apt, WIFI & Office, Near State Fair

This beautifully furnished upper duplex offers a cozy and comfortable living space in a safe and peaceful neighborhood. The kitchen comes fully equipped with all the necessary supplies for cooking and dining, and the garage and driveway provide convenient parking options. Stay connected with the included WIFI and watch YouTube TV. Nice Office space. Conveniently located near major freeways, downtown, hospitals, and the State Fair Grounds. Book now for a stress-free and enjoyable stay

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.

✺ La Casita ✺ 3 Bedrooms ✺ Spacious Parking ✺

La Casita is a 1930’s two-story bungalow home located in West Allis, WI. Short walking distance from Wisconsin State Fair Park, Pettit National Ice Center, and close to major highways. Enjoy the Mexican theme decor along with the natural woodwork throughout! Plenty of free off street parking available. Amenities include: Self Check-In, WiFi, Roku TV with Hulu & HBO Max, Fully Stocked Kitchen, Hairdryer, Fresh Sheets and Towels, Washer and Dryer, Reading Material, and much more!

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.

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!