
Family-friendly holiday 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.

Modern Lake Country Farmhouse in Delafield
Just a half mile outside downtown Delafield, this charming, modern farmhouse is clean, updated and well stocked. There's plenty of space to have a peaceful, relaxing stay. Easy access to golf, lakes (like Nagawicka and Upper & Lower Nemahbin), parks (like Lapham Peak State Park), hiking, biking and x-country skiing. Enjoy walking access to restaurants and shops in Delafield. Just minutes off I-94 in Lake Country, conveniently located between Milwaukee and Madison. 30 minutes from Fiserv Forum.

Exhale, rest
Exhale. The perfect combination. This home is right in the village of Menomonee Falls with great shopping and restaurants within walking distance. Close to the highway, it’s also a mere half an hour to anything Milwaukee so games, museums, festivals are all also at your fingertips. At the end of dead end road with views of the river, access to trails, and a secluded deck and fire pit, there is definitely also a rural feel. This location has it all. Go out, live life, come back, exhale and rest.

Beautifully Restored Historic Victorian
Whether this is for a single, couple, or small group, your stay at this historic home will truly be memorable. You’ll love the MBR suite featuring a gas fireplace, whirlpool tub, and double walk-in custom tile shower. There is an additional very nice full bath/shower on the main floor. The finished lower level has two separate rooms, each with a quality double futon with bedding available for your guests. For this attractive price, the upper 4 bedrooms are locked but may be opened for more

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.

Cozy cottage in the heart of Lake Country
Entire cottage in the heart of Lake Country. Merryhill Cottage is nestled on two acres with mature trees. Included on the two acres- the host's farmhouse, a guest house and barn. The feeling of a country setting but with easy access to Hwys 16, 83 and I 94. Close to shopping, restaurants, parks, hiking, cross country skiing and snowshoeing, lakes, and beaches (10 min. to Delafield and Oconomowoc and 15 min. to Pewaukee.) Perfect for day trips to Madison (54 min.) and Milwaukee (30 min.).

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.

Relax close to everything in Milwaukee
Ranch Style home in a quiet Neighborhood. You will feel at home and comfortable! The home is well maintained and very clean. In the winters you could cozy up to a nice fire upstairs and relax with a glass of wine. Downstairs is a second fireplace you have going and play a game of pool. In The summer you can enjoy the three seasons room, with looking a cup of coffee and look at the planted flower garden. Close to the Wauwatosa village down town. Even closer to Elm Grove Village.

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.

Cozy 2BR charm | Big Yard, Fire pit, Replenishing!
Wake up to the sunrise over a peaceful backyard and enjoy your favorite blend on your private balcony. Evenings are perfect by the fire pit under a starry sky. This renovated home has gas stove/oven, microwave, coffee maker, full-size fridge/freezer, in-unit washer & dryer, smart TV, and Wi-Fi - ideal for couples, small families, or traveling professionals. Only 1 mile from I-94 and 20 minutes from Milwaukee, blending quiet comfort with city convenience.

Historic on The Avenue
Entire Home- 3 bedrooms This beautiful historic home is centrally located in the heart of Wauwatosa! Steps from the quaint village with restaurants, bars, coffee shops and boutiques! This property marries old world charm with modern amenities. Less than 15 minutes via freeway to downtown Milwaukee, the lakefront, Marquette University, less than 10 minutes to American Family Field, 5 minutes to the Milwaukee Zoo and Froedtert/Children's hospital.

3 Bedroom Muskego Home
Be our guest in a Country like 1,800 sq ft home nestled in a wetlands setting with a 1 car garage. Sleeps 6 in a master suite and 2 smaller bedrooms. Home has 2 full bathrooms with 2 showers. Full kitchen with a refrigerator and a dishwasher. Has a Laundry room with washer and dryer. A gas stone fireplace graces the family room. A Large deck is out back with an outdoor gas grill. Also, a 220 Volt EV charger is available for your use

Clean 2 bedroom/1 bath close to everything!
Charming, recently and tastefully furnished 2 bedroom 1 bathroom apartment with private entrance and parking. Close to downtown, shopping malls, zoo, hospital, airport, and main freeways. Full kitchen with stove, microwave, coffee pot, toaster, and kitchenware. Unit has TVs and WiFi. Coin operated laundry is accessible in building. Why stay at a hotel when you can feel at home in this lovely unit?
Popular amenities for Waukesha family-friendly rentals
Family-friendly home rentals with a hot tub

Happy Days Home close to all MKE attractions

Brewers Hill Gem w/hot tub & seasonal shared pool

Clementine Cottage

The Little Gray House

Exquisite Modern A-frame all WithInnReach

Belleview House: Hot Tub, Backyard, Fire Table

Meracle Acres

Cabin Outdoor HotTub Sleeps 7 Pet Friendly
Family- and pet-friendly home rentals

Peaceful weekend or extended stay, full amenities

Lake Michigan Writer’s Cabin

Beautiful home on Okauchee Lake, WI

Entire Wauwatosa Home!

Charming log cabin in the woods

That 70s Bungalow

Quiet retreat-golf, bike, hike, motorcycle

Historic cottage with fireplace. Pets Welcome!
Family-friendly home rentals with a pool

The Landis, elegant condo w/ king bed & fireplace!

LakeView-SummerPool-FamilyFriendly-CloseToTown

LG Quaint Condo on Lakeshore Dr.

Relaxing Villa with Amazing Amenities!

Luxury Log Cabin retreat home

Lake Geneva relaxation!

Lake Geneva Cloud 9

Lakeview at CasaComo
When is the best time to visit Waukesha?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $200 SGD | $193 SGD | $197 SGD | $214 SGD | $246 SGD | $343 SGD | $349 SGD | $301 SGD | $246 SGD | $246 SGD | $248 SGD | $243 SGD |
| Avg. temp | -4°C | -3°C | 3°C | 8°C | 14°C | 20°C | 23°C | 22°C | 18°C | 12°C | 5°C | -1°C |
Quick stats about holiday rentals that are family-friendly in Waukesha

Total holiday rentals
Explore 20 holiday rentals in Waukesha

Nightly prices starting at
Waukesha holiday rentals start at $51 SGD per night before taxes and fees

Verified guest reviews
Over 660 verified reviews to help you choose

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Waukesha holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Waukesha rentals

4.5 Average rating
Waukesha stays receive an average rating of 4.5 out of 5 from guests
Destinations to explore
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- Twin Cities Holiday rentals
- Six Flags Great America
- Alpine Valley Resort
- Wilmot Mountain Ski Resort
- Erin Hills Golf Course
- Illinois Beach State Park
- Milwaukee County Zoo
- Bradford Beach
- Milwaukee Public Museum
- Sunburst
- Baird Center
- Discovery World
- Riverside Theater
- Little Switzerland Ski Area
- Marquette University
- Fiserv Forum
- Betty Brinn Children's Museum
- Gurnee Mills
- Lake Park
- Lake Geneva Cruise Line
- Holy Hill National Shrine of Mary
- Lake Geneva Public Library
- South Shore Park
- Kettle Moraine State Forest - Northern Unit
- American Family Insurance Amphitheater




