Family-friendly vacation 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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Guest favorite

Cottage in Richfield

4.95 out of 5 average rating, 238 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.

Nov 22 – 29

R3,413 ZAR per night

Guest favorite

Guesthouse in Milwaukee

4.95 out of 5 average rating, 246 reviews

The Carriage House in Sanger House Gardens

Located in the grounds of the picturesque Victorian Sanger House gardens this secluded downtown Milwaukee location is perfect for boutique weddings, events and stays. The Carriage House accommodation has been tastefully restored by the current Hosts providing luxury accommodation unparalleled in the area. The enchanting house itself can comfortably accommodate two guests and has all modern conveniences. Access to the numerous picturesque sitting areas in the garden is included in your stay.

Apr 14 – 21

R1,965 ZAR per night

Superhost

Place to stay in Racine

4.86 out of 5 average rating, 621 reviews

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. And if we're home, a complimentary Chai for you! Come, make lifelong memories at Racine's Best Kept Secret!

Oct 6 – 13

R3,950 ZAR per night

Guest favorite

Guest suite in Sussex

4.96 out of 5 average rating, 240 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.

Dec 25 – Jan 1

R1,915 ZAR per night

Guest favorite

Guest suite in Sussex

4.99 out of 5 average rating, 125 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.

Sep 19 – 26

R2,743 ZAR per night

Superhost

Apartment in West Allis

4.78 out of 5 average rating, 269 reviews

Kegel's Inn - Studio - Classic Apartment #3

Quaint little studio with lots of old-world character. This one-room studio has original hardwood floors, heavy wood ceiling beams and 1930's tile work in the bathroom. The apartment looks down on 59th street, which for the summer months between May and November, hosts the Kegels Beer Garden on the street! We're one of the last Authentic German restaurants and Inn's left in country and the studio apartment is right above it! We hope you love this place as much as we do!

Jan 17 – 24

R1,897 ZAR per night

Guest favorite

Apartment in West Allis

4.91 out of 5 average rating, 255 reviews

The Cheese House

Large well appointed two bedroom, living room, dining room, kitchen, and private balcony. Apartment is located on the second floor right above the award winning West Allis Cheese & Sausage Shoppe. Each stay includes 4 breakfast sandwiches and house coffee vouchers for the cheese store cafe. The rental is centrally located minutes from Pettit National Ice Center, Milwaukee County Zoo, Wisconsin State Fair, and Brewers Stadium not to mention local restaurants.

Nov 9 – 16

R1,879 ZAR per night

Guest favorite

Guesthouse in Milwaukee

4.86 out of 5 average rating, 274 reviews

Cozy Brewer's Hill Coach House

Studio coach house is up stairs above garage and on a quiet street. Included kitchen, bathroom, one Queen bed and some seating, being 2 blocks away from a skyline view and nearby bars. 1 parking space is included. Cats and dogs OK. This is a perfect space to come back to after a day of adventuring in Milwaukee. We love this city and have lots of suggestions on things to do, places to eat and how to get around!

Apr 14 – 21

R2,041 ZAR per night

Guest favorite

Cabin in Kenosha

4.81 out of 5 average rating, 538 reviews

Lake Michigan Writer’s Cabin

Beautiful Lake Michigan retreat perfect for relaxing, boating, fishing, swimming and more! Fully remodeled. Perfect for ice fishing in the winter. A Sportsman’s paradise. Ideal for the adventurous. Relax, do some writing or work overlooking the breathtaking scenery. A stone's throw to the beach. Massive deck overlooking the tranquil landscape. A short walk to downtown shops, cafes and restaurants.

Dec 27 – Jan 3

R2,064 ZAR per night

Guest favorite

Cabin in Hubertus

4.96 out of 5 average rating, 482 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.

Dec 17 – 24

R4,378 ZAR per night

Guest favorite

Apartment in Fort Atkinson

4.96 out of 5 average rating, 218 reviews

‘The Part Time Local’ - A boho small town retreat.

A cozy, comfortable 1 bedroom apartment with eat in kitchen and separate living room. Newly remodeled bathroom with tiled shower. Mahogany floors and all the charm you'd expect in a 1907 Arts & Crafts. Stylish, boho décor to make anyone feel right at home. Private balcony with Rock River views. Laundry available. Downtown Fort Atkinson, walking distance to everything!

Oct 8 – 15

R2,468 ZAR per night

Guest favorite

Apartment in Port Washington

4.92 out of 5 average rating, 250 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.

Oct 14 – 21

R1,846 ZAR per night