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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.

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Guest favourite
The exterior of a charming house is showcased, featuring a welcoming front porch adorned with string lights. Lush greenery surrounds the home, with a flower garden displaying purple blooms. A pathway leads to the entrance, enhancing the inviting atmosphere of the property.
Home in Menomonee Falls
4.93 out of 5 average rating, 172 reviews

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.

Top Guest favourite
A historic home features a multi-gabled roof and intricate architectural details. The exterior showcases a blend of light and dark hues, complemented by well-maintained landscaping and a spacious lawn. A charming porch wraps around the front, providing an inviting entrance with rocking chairs nestled on one side.
Home in Wales
4.94 out of 5 average rating, 194 reviews

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

Top Guest favourite
A two-story house is surrounded by a snow-blanketed yard, with tall trees silhouetted against a twilight sky of vibrant pinks and purples. The warm glow of lights from the front windows contrasts with the cool tones of the winter scenery.
Guest suite in Brookfield
5 out of 5 average rating, 257 reviews

In the Canopy (beautiful Brookfield/Milwaukee)

Relax “in the Canopy” of beautiful maples! If you’re looking for party central…this isn’t it. But if you want a comfortable place in a tree-filled neighborhood, just a few minutes from all the best Milwaukee has to offer, you’re in luck! Perfect location for quick access to the city—or to Lake Country to the west. Quiet, comfortable, safe, surrounded by beautiful gardens. We’re in a perfect launching spot to visit Summerfest, Brewers/Bucks games, or Milwaukee's western suburbs. Bring the kids!

Guest favourite
A bright living area showcases a comfortable seating arrangement with decorative cushions. Potted plants add greenery, and light streams in through the large windows. Artwork adorns the walls, while a mix of textures is provided by the rugs and furnishings.
Apartment in Bay View
4.94 out of 5 average rating, 381 reviews

Bay View MKE Hideaway - with Parking!

Cozy, inviting, one bedroom apartment in the heart of Bayview, literally steps away from some of Milwaukee's best restaurants, bars and shops! One of two Airbnb guest spaces in our house, this downstairs apartment is our home base when we're in Milwaukee, and we love sharing it with guests when we’re on the road! We are within five minutes of Summerfest grounds and East Side & Historic Third Ward districts, and within 10 minutes of the airport, downtown, Marquette University, and Miller Park.

Top Guest favourite
A historic stone home is presented, featuring multiple windows that enhance its classic appeal. A well-maintained garden with colorful flowers surrounds the exterior, creating a welcoming entrance to the Butler Place. A sign displaying the property's name is held by two guests in front of the house.
Guest suite in Sussex
4.96 out of 5 average rating, 320 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.

Top Guest favourite
A spacious sleeping area is furnished with a large bed, complimented by soft white linens. A wooden dresser and a chair provide storage and seating options. Natural light filters through a nearby door, enhancing the welcoming ambiance of the room.
Bungalow in Wauwatosa
4.96 out of 5 average rating, 224 reviews

Tosa Respite (second floor, private suite)

Beautiful, private, second floor suite nestled in a quaint Wauwatosa neighborhood, Tosa Respite is a getaway within the city. Tosa Respite is conveniently located a stone’s throw from Interstate 94, Froetdert Hospital, The Medical College of WI, the Ronald McDonald House, State Fairgrounds, and biking/walking trails. Also walking distance to shops, cafés, restaurants, with a Bublr hub around the corner. Owner lives on premise and operates a private studio on the first floor.

Guest favourite
A brightly colored living area features an orange couch with patterned cushions, complemented by a unique coffee table. A round ottoman sits nearby, while large windows allow ample natural light. Open shelving holds decorative items, enhancing the vibrant atmosphere of the open-concept space.
Home in Bay View
4.94 out of 5 average rating, 122 reviews

Bright 1.5BR in the Heart of Bay View - w/ Parking

Perfectly located in Milwaukee’s eclectic Bay View 4 blocks from the lake. Minutes from downtown, Summerfest, art museum, etc. You’ll have the entire second floor of this sunny duplex. The space is open concept - 1 bed with a King Casper mattresses, a bright kitchen with tons of space, a stylish living room with art throughout, and an office (with an air mattress). Fenced-in back yard that's great for pets and chill around the outdoor table for optimal hangs and BBQs.

Top Guest favourite
A spacious bed is dressed in neutral linens, complemented by a decorative striped blanket and a pillow with 'relax' text. A wooden bedside table with a lamp rests nearby, and wall art is mounted above the bed, enhancing the room's inviting ambiance.
Apartment in Wauwatosa
4.86 out of 5 average rating, 359 reviews

Tosa Village Studio Apartment

Tosa Village Studio. (Wauwatosa is the first suburb west of Milwaukee). Walk to the Village and explore the boutique shops, restaurants and bars. Enjoy summer concerts in Hart Park. Miller Park (Milwaukee County Stadium - Home of the Brewers) only 3.5 miles away. Close to the Medical Complex, Froedert and Children's Hospitals. 6.5 miles to the Fiserv Forum (Home of the Milwaukee Bucks). Six miles to downtown Milwaukee. Enjoy Summerfest at the Lake Michigan shore.

Guest favourite
Townhouse in Waukesha
4.93 out of 5 average rating, 184 reviews

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.

Guest favourite
A cozy studio space features a spacious bed with soft linens, a light-colored coffee table, and a modern gray couch adorned with decorative pillows. Two wall art pieces are displayed above the couch, and a large mirror reflects the inviting atmosphere.
Home in Waukesha
4.96 out of 5 average rating, 102 reviews

Brand New Studio w. Private Entry + Garden Patio

Beautiful studio unit, sleeps 3. Professionally landscaped patio for morning coffee, or late night stargazing. Free parking, 3 miles from I94, W/D, fully stocked kitchenette, induction stove, microwave, deluxe coffee maker, toaster oven, mini refrigerator, WiFI, Smart TV, Wireless Printer,, private fenced yard, patio heater for chilly nights. Telescope experience available for stargazing. Perfect for the traveling professional, or couple.

Top Guest favourite
A quiet country home is nestled among trees and well-maintained shrubs, showcasing a wide, inviting front lawn. The façade features a mix of symmetry with multiple windows and a central entrance, complemented by a light-colored exterior that reflects a serene environment.
Home in Muskego
4.97 out of 5 average rating, 185 reviews

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

Guest favourite
Home in West Allis
4.94 out of 5 average rating, 265 reviews

Near to all Milwaukee favorites/ Free Parking/WiFi

Make yourself, family or friends at home in this Cozy comfortable upper 2 bedroom, 1 bathroom house with Wisconsin charm! It’s a great location in the city of West Allis just a short drive to everywhere in Milwaukee. I appreciate that you considered my Airbnb listing! Please feel free to contact me on how I can improve your stay. Also, please take a moment to review my house rules. Can wait to host you, thanks!!!

Popular amenities for Waukesha family-friendly rentals

When is the best time to visit Waukesha?

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Avg. price$270 NZD$262 NZD$267 NZD$289 NZD$333 NZD$465 NZD$473 NZD$407 NZD$333 NZD$331 NZD$260 NZD$260 NZD
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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 $69 NZD per night before taxes and fees

  • Verified guest reviews

    Over 600 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Waukesha holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Waukesha rentals