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Family-friendly vacation rentals in Waukesha County

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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
$348 CAD per night
Guest favourite
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. 18 – 25
$131 CAD per night
Guest favourite
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.
Feb. 16 – 23
$150 CAD per night

Popular amenities for Waukesha County family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Cabin in Elkhorn
The Retreat: 5 Acre Log Cabin
Oct. 1 – 8
$1,249 CAD per night
Guest favourite
Home in Kenosha
The Retreat on Lake Michigan 6 bd/4bth 4000 sq ft
Nov. 4 – 11
$1,034 CAD per night
Guest favourite
Home in Kenosha
Coastal Style Estate
Sep. 22 – 29
$995 CAD per night
Guest favourite
Home in Milwaukee
Spacious house, yard & hot tub easy drive downtown
Mar. 3 – 10
$960 CAD per night
Guest favourite
Cabin in Lake Geneva
Luxury Log Cabin retreat home
Mar. 3 – 10
$781 CAD per night
Superhost
Condo in Lake Geneva
2 Bedroom villa at Lake Geneva's GRAND Resort
Jan. 15 – 22
$620 CAD per night
Superhost
Condo in Lake Geneva
Grand Geneva in Lake Geneva
Jan. 4 – 11
$350 CAD per night
Superhost
Condo in Lake Geneva
Condo onsite Grand Geneva Resort Golf Ski Spa
Nov. 18 – 23
$1,610 CAD per night
Condo in Lake Geneva
NEW! Updated Lake Geneva Resort Luxury Suite
May 22 – 29
$347 CAD per night
Home in Lake Geneva
Restored Victorian w Hottub , 1block to shops
Oct. 12 – 19
$520 CAD per night
Condo in Wauwatosa
Stylistic Condo Hot Tub Tosa Village 2 blocks away
Aug. 5 – 12
$714 CAD per night
Superhost
Apartment in Lake Geneva
Deluxe villa at Lake Geneva's Most GRAND Resort
Jan. 28 – Feb. 4
$354 CAD per night

Family- and pet-friendly home rentals

Superhost
Apartment in West Allis
Station No 06 Inn
Oct. 25 – Nov. 1
$182 CAD per night
Guest favourite
Cabin in Kenosha
Lake Michigan Writer’s Cabin
Nov. 28 – Dec. 5
$214 CAD per night
Guest favourite
Guesthouse in Hubertus
Quiet retreat-golf, bike, hike, motorcycle
Sep. 10 – 17
$279 CAD per night
Guest favourite
Cottage in Richfield
Peaceful weekend or extended stay, full amenities
Nov. 26 – Dec. 3
$269 CAD per night
Superhost
Chalet in Williams Bay
The Bay Chalet
Nov. 9 – 16
$556 CAD per night
Guest favourite
Apartment in Milwaukee
Riverwest Loft with city skyline view
Dec. 30 – Jan. 6
$158 CAD per night
Guest favourite
Home in Milwaukee
This Must Be the Place- Bayview Bohemian Vibes
Mar. 17 – 24
$283 CAD per night
Superhost
Apartment in Milwaukee
Cozy Basement Space In Bay View by Lake Michigan
Oct. 13 – 20
$89 CAD per night
Guest favourite
Home in Wauwatosa
Wonderful craftsman home in Wauwatosa
Jan. 21 – 28
$374 CAD per night
Guest favourite
Home in Shorewood
No Cleaning Fee! Eclectic home w/yard & parking
Apr. 4 – 11
$453 CAD per night
Guest favourite
Home in Milwaukee
HGTV Renovated Home with GREAT backyard!
Mar. 18 – 25
$678 CAD per night
Guest favourite
Home in Milwaukee
Historic 4 Bdr Victorian near Brady Street
Mar. 2 – 9
$585 CAD per night

Family-friendly home rentals with a pool

Superhost
Condo in Lake Geneva
Flexible rental In Lake Geneva Area
Nov. 23 – 30
$200 CAD per night
Condo in Lake Geneva
Lakeview at CasaComo
Sep. 8 – 15
$319 CAD per night
Guest favourite
Condo in Lake Geneva (Town of Geneva)
Private & Cozy Villa on Zurich in LG
Dec. 29 – Jan. 5
$394 CAD per night
Home in Waukesha
Frank Lloyd Wright style home near Milwaukee
Feb. 3 – 10
$1,580 CAD per night
Apartment in Milwaukee
Downtown One Bedroom Apartment #305
May 25 – Jun. 1
$182 CAD per night
Villa in Lake Geneva
Lake Geneva Relaxing Retreat
Jan. 15 – 22
$728 CAD per night
Home in Sussex
2017 US Open Erin Hills Home
Nov. 16 – 23
$1,700 CAD per night
Home in Sussex
Beautiful home in the country
Jun. 25 – Jul. 2
$519 CAD per night
Superhost
Villa in Lake Geneva
2 Bedroom Villa at Lake Geneva's GRAND Resort
Oct. 13 – 20
$747 CAD per night
Superhost
Condo in Lake Geneva
2 Bedroom villa at Lake Geneva's GRAND Resort
Jan. 4 – 11
$620 CAD per night
Guest favourite
Condo in Lake Geneva
2 Bedroom villa at Lake Geneva's GRAND Resort
Oct. 4 – 11
$747 CAD per night
Superhost
Condo in Oconomowoc
Olympia VOA Oconomowoc WI Great getaway for fun
Mar. 19 – 26
$266 CAD per night

Destinations to explore