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Family-friendly vacation rentals in Waukesha County

Find and book unique family-friendly homes on Airbnb

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Top-rated family-friendly rentals in Waukesha County

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

Superhost
Place to stay in Racine
Wisconsin Treehouse Getaway!
Featured in Timeout Magazine as Chicago's Top 10 secluded 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!
Jun 11 – 18
$191 per night
4.87 out of 5 average rating, 601 reviews
Guest favorite
Townhouse in Milwaukee
Vintage Bay View - Big Backyard, Big 1 Bedroom
Welcome to your Milwaukee getaway! Located in the Bay View area, you're walking distance from the best farm-to-table restaurants, music venues, art fairs, and craft beer in the city. Not only that, but Lake Michigan's beaches, Miller Park, and downtown are a short drive away. The location is ideal. The place was created with a 70's midwestern feel, with wood-paneled furniture pieces and mod design. It also boasts a giant kitchen and backyard with grill. We can't wait for you to visit!
Mar 24 – 31
$65 per night
4.94 out of 5 average rating, 352 reviews
Guest favorite
Guest suite in Sussex
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.
Oct 24 – 31
$88 per night
4.96 out of 5 average rating, 233 reviews

Popular amenities for Waukesha County family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
Cabin in Elkhorn
The Retreat: 5 Acre Log Cabin
Oct 1 – 8
$691 per night
4.97 out of 5 average rating, 260 reviews
Guest favorite
Home in Kenosha
The Retreat on Lake Michigan 6 bd/4bth 4000 sq ft
Feb 16 – 23
$600 per night
4.92 out of 5 average rating, 120 reviews
Guest favorite
Home in Kenosha
Coastal Style Estate
Sep 23 – 30
$533 per night
4.91 out of 5 average rating, 233 reviews
Guest favorite
Home in Milwaukee
Spacious house, yard & hot tub easy drive downtown
Mar 7 – 14
$567 per night
4.93 out of 5 average rating, 224 reviews
Guest favorite
Cabin in Lake Geneva
Luxury Log Cabin retreat home
Mar 3 – 10
$407 per night
4.84 out of 5 average rating, 98 reviews
Superhost
Condo in Lake Geneva
2 Bedroom villa at Lake Geneva's GRAND Resort
Jan 15 – 22
$354 per night
4.82 out of 5 average rating, 60 reviews
Superhost
Condo in Lake Geneva
Grand Geneva in Lake Geneva
Jan 5 – 12
$209 per night
4.5 out of 5 average rating, 10 reviews
Superhost
Condo in Lake Geneva
Condo onsite Grand Geneva Golf Resort Ski Spa
Nov 19 – 24
$950 per night
New place to stay
Condo in Lake Geneva
NEW! Updated Lake Geneva Resort Luxury Suite
Jul 5 – 12
$260 per night
4.6 out of 5 average rating, 129 reviews
Home in Lake Geneva
Restored Victorian w Hottub , 1block to shops
Oct 12 – 19
$283 per night
4.68 out of 5 average rating, 117 reviews
Condo in Wauwatosa
Stylistic Condo Hot Tub Tosa Village 2 blocks away
Aug 4 – 11
$393 per night
4.63 out of 5 average rating, 107 reviews
Superhost
Apartment in Lake Geneva
Deluxe villa at Lake Geneva's Most GRAND Resort
Feb 2 – 9
$203 per night
5.0 out of 5 average rating, 6 reviews

Family- and pet-friendly home rentals

Superhost
Apartment in West Allis
Station No 06 Inn
Oct 26 – Nov 2
$89 per night
4.79 out of 5 average rating, 150 reviews
Guest favorite
Cabin in Kenosha
Lake Michigan Writer’s Cabin
Oct 28 – Nov 4
$116 per night
4.8 out of 5 average rating, 521 reviews
Guest favorite
Guesthouse in Hubertus
Quiet retreat-golf, bike, hike, motorcycle
Sep 12 – 19
$167 per night
4.96 out of 5 average rating, 133 reviews
Guest favorite
Cottage in Richfield
Peaceful weekend or extended stay, full amenities
May 11 – 18
$157 per night
4.95 out of 5 average rating, 236 reviews
Superhost
Chalet in Williams Bay
The Bay Chalet
Nov 9 – 16
$299 per night
4.87 out of 5 average rating, 205 reviews
Guest favorite
Apartment in Milwaukee
Riverwest Loft with city skyline view
Sep 10 – 17
$81 per night
4.86 out of 5 average rating, 364 reviews
Superhost
Guest suite in Milwaukee
Basement Bay View Suite,express bus airport-north
Jan 12 – 19
$43 per night
4.81 out of 5 average rating, 99 reviews
Guest favorite
Home in Milwaukee
This Must Be the Place- Bayview Bohemian Vibes
Mar 9 – 16
$137 per night
4.95 out of 5 average rating, 104 reviews
Superhost
Apartment in Milwaukee
Cozy Basement Space In Bay View by Lake Michigan
Oct 13 – 20
$45 per night
4.84 out of 5 average rating, 165 reviews
Guest favorite
Home in Shorewood
No Cleaning Fee! Eclectic home w/yard & parking
Apr 4 – 11
$270 per night
4.96 out of 5 average rating, 186 reviews
Guest favorite
Home in Wauwatosa
Wonderful craftsman home in Wauwatosa
Jan 26 – Feb 2
$198 per night
4.85 out of 5 average rating, 218 reviews
Guest favorite
Home in Milwaukee
HGTV Renovated Home with GREAT backyard!
Aug 25 – Sep 1
$556 per night
4.95 out of 5 average rating, 167 reviews

Family-friendly home rentals with a pool

Superhost
Condo in Lake Geneva
Flexible rental In Lake Geneva Area
Feb 10 – 17
$100 per night
4.65 out of 5 average rating, 244 reviews
Condo in Lake Geneva
Lakeview at CasaComo
Jan 6 – 13
$177 per night
4.9 out of 5 average rating, 188 reviews
Guest favorite
Condo in Lake Geneva (Town of Geneva)
Private & Cozy Villa on Zurich in LG
Sep 25 – Oct 2
$179 per night
4.93 out of 5 average rating, 239 reviews
Home in Waukesha
Frank Lloyd Wright style home near Milwaukee
Feb 5 – 12
$850 per night
4.94 out of 5 average rating, 16 reviews
Apartment in Milwaukee
Downtown One Bedroom Apartment #305
Aug 15 – 22
$102 per night
4.65 out of 5 average rating, 127 reviews
Villa in Lake Geneva
Lake Geneva Relaxing Retreat
Jan 15 – 22
$402 per night
5.0 out of 5 average rating, 6 reviews
Home in Sussex
2017 US Open Erin Hills Home
Nov 18 – 25
$1,000 per night
New place to stay
Home in Sussex
Beautiful home in the country
Jan 20 – 27
$278 per night
New place to stay
Superhost
Villa in Lake Geneva
2 Bedroom Villa at Lake Geneva's GRAND Resort
Jan 16 – 23
$354 per night
4.88 out of 5 average rating, 68 reviews
Superhost
Condo in Lake Geneva
2 Bedroom villa at Lake Geneva's GRAND Resort
Oct 18 – 25
$391 per night
5.0 out of 5 average rating, 4 reviews
Guest favorite
Condo in Lake Geneva
2 Bedroom villa at Lake Geneva's GRAND Resort
Jan 9 – 16
$354 per night
4.71 out of 5 average rating, 7 reviews
Superhost
Condo in Oconomowoc
Olympia VOA Oconomowoc WI Great getaway for fun
Mar 21 – 28
$153 per night
4.22 out of 5 average rating, 18 reviews

Destinations to explore