Waukesha County family rentals

We found 674 family rentals — enter your dates for availability

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November 2025

December 2025

Find the best place to stay - Waukesha County

Showing deals for: 18 Feb - 21 Feb

The boathouse and pier at Lakewood Farms lake house

Premier Host

Family Retreat, private, large, great for multi-family, company retreat, wedding

Sleeps 36 · 11 bedrooms · 5+ bathrooms

for 3 nights, 1 home

AU$2,716 per night

includes taxes & fees

Kohl Manor Luxury Lake 8-br exclusive retreat Pool, Cinema, Arcade on LacLaBelle

Sleeps 17 · 8 bedrooms · 5 bathrooms

for 3 nights, 1 home

AU$6,287 per night

includes taxes & fees

Premier Host

Spacious Lake House with Beautiful Views and 123 Feet of Swimming Frontage

Sleeps 13 · 5 bedrooms · 3+ bathrooms

for 3 nights, 1 home

AU$1,489 per night

includes taxes & fees

Premier Host

Fantastic Voyage on Pewaukee Lake| Location, Comfort, Experience

Sleeps 6 · 2 bedrooms · 2 bathrooms

for 3 nights, 1 home

AU$570 per night

includes taxes & fees

Premier Host

Magnificently restored, charming, 8+ Bed-Victorian on a beautiful 1.5 acres.

Sleeps 16 · 5 bedrooms · 3 bathrooms

for 3 nights, 1 home

AU$751 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Waukesha County

Family Retreat, private, large, great for multi-family, company retreat, wedding

Wooded Hills/Indoor Pool/Hot Tub/Arcade

Kohl Manor Luxury Lake 8-br exclusive retreat Pool, Cinema, Arcade on LacLaBelle

Spacious Lake House with Beautiful Views and 123 Feet of Swimming Frontage

Fantastic Voyage on Pewaukee Lake| Location, Comfort, Experience

Magnificently restored, charming, 8+ Bed-Victorian on a beautiful 1.5 acres.

Find spaces that suit your style

Family-friendly Rentals in Waukesha County

Holiday Rental options in Waukesha County