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Family-friendly holiday rentals in Waukesha

Find and book unique family-friendly homes on Airbnb

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 $56 AUD per night before taxes and fees

  • Verified guest reviews

    Over 760 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • 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

  • 4.8 Average rating

    Waukesha stays are highly rated by guests—averaging 4.8 out of 5!

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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Top Guest favourite
The modern farmhouse is viewed from a distance, showcasing its clean white exterior and well-maintained landscaping. A paved driveway leads to the entrance, flanked by neatly trimmed bushes and vibrant green grass, creating an inviting approach to the home.
Home in Delafield

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.

Indoor spacesKitchenParking

4.99 out of 5 average rating, 169 reviews
Top Guest favourite
A two-story home is surrounded by vibrant autumn foliage, featuring large trees displaying rich yellow and orange leaves. A gravel driveway leads up to the house, with fallen leaves carpeting the ground. A garage is visible in the background, adding to the serene neighborhood setting.
Guest suite in Brookfield

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!

FamilyKitchenGetting around

5.0 out of 5 average rating, 285 reviews
Guest favourite
Home in Waukesha

The Cozy Coop | Private Upstairs Retreat | Sleep 8

Wake up to sunrise over a peaceful backyard and enjoy your morning coffee off the balcony. Evenings are perfect by the fire pit under a starry sky. Just 5 minutes from Pewaukee Lake This private upper level comes with a large fenced in yard - ideal for relaxing and spending time together. Open-concept living, kitchen, and dining area creates a warm, inviting space to gather. Sleeps up to 8 and is best suited for small families or close-knit groups who prefer a more cozy, intimate layout.

KitchenIndoor spacesBackyard

4.92 out of 5 average rating, 212 reviews
Guest favourite
A charming home is set among lush greenery, showcasing large windows that allow plenty of natural light. A stone wall supports a decorative patio area with several outdoor chairs and potted plants, creating a serene outdoor space. Tall trees frame the scene.
Home in Nashotah

Beautiful home on Okauchee Lake, WI

I have a beautiful home on a fun lake. It is just 25 mins from Milwaukee and 50 mins from Madison. There are several bars and restaurants on&off the water; you can either walk, drive or boat to. I have a boat slip available if you want to bring your own 18' or smaller boat. There is a fire-table on the patio for those quiet nights sitting out under the stars. Winter is spectacular here too. Nearby is the Nashotah Park, with a dog park and hiking trails. Lions park has an area for parties.

KitchenFamilyBarbecue

4.93 out of 5 average rating, 120 reviews
Guest favourite
A two-story house features a blue exterior with large windows illuminated by natural light. Lush green shrubs flank the entrance, while a small seating area consisting of metal chairs is set on a well-maintained lawn. A concrete path leads to the front door.
Home in Oconomowoc

Oconomowoc Downtown River View

Stunning view of the Oconomowoc river, locate in the heart of downtown Oconomowoc. Whether you are traveling for fun or work there is something for everyone. Walk to sandy beaches, six nearby parks, tennis court, or just walk around beautiful Lac La Belle Lake and Fowler Lake. Bring your kayaks or boat. Local boat rentals are available in town. Enjoy live bands and events at restaurants and bars or have a peaceful dinner at one of many fine dining restaurants also in walking distance.

KitchenFamilyValue

4.86 out of 5 average rating, 132 reviews
Top Guest favourite
A spacious living area showcases a dark gray sectional sofa adorned with yellow and patterned cushions. A coffee table sits at the center on a patterned area rug, while a wall-mounted television is mounted nearby. Natural light enters through windows with a neutral-colored wall in the background.
Home in Delafield

Nagawicka Woods-Beautiful Lake Country Ranch Home

Welcome to Nagawicka Woods, a beautiful home located in Delafield, WI in the heart of Lake Country. Minutes from lake access to: Nagawicka, Okauchee, Pewaukee, Pine, Namahbin & Oconomowoc Lakes. 2 blocks from St. John's NW Military Academy, 6 minutes from Rogers Memorial Hospital, half an hour from Milwaukee & one hour from Madison. This home sleeps 6 (a pack n play is available.) Ideal for couples, family, small groups or a girlfriends getaway. Set on a quiet 1.5 private acres.

Indoor spacesFamilyAccess

4.95 out of 5 average rating, 197 reviews
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

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.

FamilyKitchenSleep quality

4.96 out of 5 average rating, 348 reviews
Top Guest favourite
A newly remodeled kitchen features wooden cabinetry and a dark countertop, paired with modern appliances. A large sink and a stovetop are highlighted, along with a window that provides a view of the outside. The flooring is made of warm wood, enhancing the overall design.
Home in Wauwatosa

Spacious Wauwatosa Home In Prime Location

We just finished remodeling the kitchen and all 3 bathrooms in our unique tri-level mid-century modern home. There are 4 bedrooms offering an array of accommodations as well as a couch with a pull-out queen bed. If you like to cook, our new kitchen is amazing! There is a fireplace room with a lovely view outside, a laundry room and a TV with cable, a DVR, and streaming apps like Netflix. WIFI is available. This is a quiet family neighborhood. No parties and please be respectful.

Indoor spacesKitchenPets

4.98 out of 5 average rating, 221 reviews
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

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.

KitchenIndoor spacesOutdoor spaces

4.96 out of 5 average rating, 271 reviews
Superhost
A spacious dining area is furnished with a large wooden table surrounded by woven chairs. Natural light filters through multiple windows framed by cream-colored curtains. Decorated with a centerpiece of fruits, the room features warm wood paneling and a decorative chandelier overhead.
Home in West Allis

✺ La Casita ✺ 3 Bedrooms ✺ Spacious Parking ✺

La Casita is a 1930’s two-story bungalow home located in West Allis, WI. Short walking distance from Wisconsin State Fair Park, Pettit National Ice Center, and close to major highways. Enjoy the Mexican theme decor along with the natural woodwork throughout! Plenty of free off street parking available. Amenities include: Self Check-In, WiFi, Roku TV with Hulu & HBO Max, Fully Stocked Kitchen, Hairdryer, Fresh Sheets and Towels, Washer and Dryer, Reading Material, and much more!

FamilyKitchenCheck-in

4.8 out of 5 average rating, 130 reviews
Top Guest favourite
The exterior of the classic A-frame cabin, featuring a striking red facade, is set against a backdrop of lush greenery. A wooden walkway leads to a seating area with two chairs. A deck is visible, providing an inviting space to relax outdoors.
Home in Palmyra

A-Frame in forest on bike trail!

Classic A-Frame, in the woods. Borders the Kettle Moraine State Forest on 3 sides. Exterior: 2 acres, fully-fenced and dog-friendly. Hop on the "Connector" mountain bike trail right out the backyard. Or take a hike on the nearby Ice Age trail, Bald Bluff, John Muir, Nordic, or snowmobile trails. Interior: 1,500 square feet, 2 levels, open concept main living area with loft ceiling, wood-burning fireplace, 2 arcade machines, outdoor firepit, frisbee golf stand, etc.

FamilyIndoor spacesTV

4.99 out of 5 average rating, 104 reviews
Guest favourite
A spacious dining area features a wooden table surrounded by six chairs, complemented by an archway leading to a cozy living room. Natural light filters through large windows, illuminating the elegant combination of exposed brick and light-toned walls.
Home in Wauwatosa

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.

KitchenFamilyValue

4.96 out of 5 average rating, 170 reviews

Popular amenities for Waukesha family-friendly rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top Guest favourite
Home in Wauwatosa

The Little Gray House

KitchenIndoor spacesHot tub

5.0 out of 5 average rating, 321 reviews
Top Guest favourite
The exterior of a two-story home is visible, featuring large windows and a pleasant outdoor deck with shaded seating. A pergola is positioned nearby, surrounded by greenery and a stone pathway leading into the yard.
Home in Hubertus

Bark Lake, Entire Home, Private Lake Frontage 50ft

FamilyIndoor spacesWalkability

4.88 out of 5 average rating, 534 reviews
Guest favourite
A cozy living area is captured, featuring two patterned armchairs and a blue sofa arranged around a light coffee table. A stone fireplace anchors the space, complemented by a colorful floral artwork on the wall. Natural light filters through the windows, enhancing the inviting ambiance.
Home in Milwaukee

Happy Days Home close to all MKE attractions

FamilyIndoor spacesOutdoor spaces

4.89 out of 5 average rating, 207 reviews
Guest favourite
Townhouse in Riverwest

The Hottest Tub in MKE • Skyline Views • Sleeps 8

KitchenIndoor spacesOutdoor spaces

4.93 out of 5 average rating, 294 reviews
Guest favourite
Home in Milwaukee

Brew City Inn with Hot Tub | Summerfest House

FamilyKitchenParking

4.95 out of 5 average rating, 116 reviews
Guest favourite
An expansive wooden deck offers a welcoming outdoor space, featuring a dining table surrounded by chairs and a cozy rattan chair. A large umbrella stands in one corner, while lush greenery and blue skies create a serene backdrop.
Cabin in Elkhorn

The Retreat: 5 Acre Log Cabin

KitchenIndoor spacesCheckout

4.96 out of 5 average rating, 332 reviews
Top Guest favourite
An outdoor fire pit surrounded by wooden benches and chairs is visible in a spacious green area. The cabin in the background features a red exterior and large windows framed by trees, offering a serene spot for gathering.
Home in Elkhorn

Red Lodge|Hot Tub, Game Room, Near Lake, Free Dog!

FamilyIndoor spacesSleep quality

4.98 out of 5 average rating, 197 reviews
Guest favourite
An open concept kitchen features a large white island with seating, accompanied by modern cabinetry. The living space extends into a bright dining area, enhanced by natural light from a window. Decorative artwork and a wall clock add character to the surroundings.
Home in Milwaukee

Downtown Oasis: Hot Tub, Garage, 2 King Huge yard!

KitchenIndoor spacesAmenities

4.94 out of 5 average rating, 199 reviews

Family- and pet-friendly home rentals

Guest favourite
A single-story ranch-style home is presented, featuring a well-maintained exterior with a light-colored stone façade. Green grass surrounds the property, complemented by neatly trimmed bushes and a paved walkway leading to the front door. The roof is covered with gray shingles under a partly cloudy sky.
Home in Wauwatosa

Relax close to everything in Milwaukee

FamilyIndoor spacesBiking

4.93 out of 5 average rating, 120 reviews
Superhost
A cozy living area features a spacious sofa against a vibrant, textured wall. A colorful area rug adds warmth to the hardwood floor, while framed artwork decorates the surrounding walls. Access to the kitchen and stairway is visible in the background.
Home in West Allis

Designer Cottage-Parking, Patio, & New Kitchen

FamilyKitchenQuiet

4.81 out of 5 average rating, 209 reviews
Guest favourite
A spacious living area features a cozy seating arrangement with a dark blue sofa and two patterned armchairs around a glass coffee table. A decorative rug lies on the hardwood floor, while a modern light fixture hangs from the ceiling. A fireplace and TV are positioned on the wall.
Home in Wauwatosa

Entire Wauwatosa Home!

FamilyKitchenHeating

4.89 out of 5 average rating, 127 reviews
Guest favourite
The exterior of the vacation home features a welcoming walkway leading to the entrance. A well-maintained lawn surrounds the house, and two white chairs are positioned on a small patio, offering a pleasant outdoor seating area. Lush greenery and landscaping enhance the setting.
Holiday home in Oconomowoc

Scenic 4 Bedroom WI Lake Home - Newly Renovated!

KitchenIndoor spacesAccess

4.87 out of 5 average rating, 172 reviews
Superhost
The kitchen features dark cabinetry and modern appliances, complemented by a central wooden island with seating for two. Pendant lights hang above, illuminating the area. A window offers natural light, and open access to a hallway is visible in the background.
Townhouse in Wauwatosa

Central, Game Room, Quiet Walkable Area

Indoor spacesFamilyAccuracy

4.87 out of 5 average rating, 186 reviews
Guest favourite
A two-story grey house with white trim is presented, featuring a welcoming front porch. The porch is furnished with four bright yellow chairs, providing a cheerful spot to relax. The entrance door is located on the left, and large windows brighten the facade.
Home in Oconomowoc

Black Squirrel Farmhouse - (Downtown Oconomowoc)

Indoor spacesFamilyDecor

4.92 out of 5 average rating, 199 reviews
Guest favourite
The living area features warm wooden walls and a rustic charm. Natural light filters through large windows and skylights, illuminating a cozy seating arrangement. A small wood stove stands near a patterned area rug, while musical instruments are positioned around the space, enhancing its inviting atmosphere.
Cabin in Hubertus

Hugel Hutte - Log Cabin Getaway

Indoor spacesKitchenAmenities

4.94 out of 5 average rating, 591 reviews
Guest favourite
Cabin in Lake Geneva

Dog friendly - A-Frame adventure

FamilyKitchenQuiet

4.97 out of 5 average rating, 271 reviews

Family-friendly home rentals with a pool

Top Guest favourite
The exterior of the bungalow is highlighted by a charming front porch with a blue door. Vibrant flowers and greenery flourish along the stone landscape, providing a welcoming entrance. Large windows invite natural light into the home, complementing its classic design.
Home in Milwaukee

Rosie’s Eastside Garden Bungalow

KitchenFamilyBeach

4.97 out of 5 average rating, 123 reviews
Guest favourite
The entrance features a charming facade with three large windows and a decorative door. A set of stairs leads up to the front door, flanked by a wrought-iron railing. Lush greenery surrounds the base, enhancing the welcoming appearance of the home.
Loft in Riverwest

The Dragonfly Loft

KitchenIndoor spacesQuiet

4.87 out of 5 average rating, 715 reviews
Guest favourite
A historic Victorian-style home is showcased with a blue exterior and ornate architectural details. Bright green foliage frames the entrance, leading to the front steps. The sky is clear, enhancing the home's inviting appearance.
Home in Milwaukee

Brewers Hill Gem w/hot tub & seasonal shared pool

Indoor spacesKitchenCheck-in

4.93 out of 5 average rating, 200 reviews
Superhost
An outdoor patio space is presented, featuring a paved area surrounded by various seating options, including green chairs and a red umbrella. A grilling station is visible, and the background includes a garage with an open door. Lush greenery provides a natural border.
Home in Cudahy

Close to Lake with Great Ammenities & Breakfast!

FamilyKitchenSolo travel

4.78 out of 5 average rating, 171 reviews
Guest favourite
A 31-foot sailboat is docked in the marina, featuring a blue sail and a spacious deck. Surrounding buildings and other boats are visible in the background, under a bright sky filled with clouds.
Boat in Racine

Spacious Sailboat, “Kelly Day” sleeps 4

FamilyKitchenAccuracy

4.9 out of 5 average rating, 138 reviews
Guest favourite
A spacious living area features comfortable gray sectional sofas adorned with turquoise cushions. A light wooden coffee table is centered on a soft area rug. Soft lighting is provided by table lamps, and large sliding doors lead to an outdoor space with a view of greenery.
Home in Lake Geneva

Relaxing getaway/StepsToLake/Pool/Tennis/nearDT/WD

Indoor spacesFamilyAccuracy

4.95 out of 5 average rating, 122 reviews
Top Guest favourite
A manicured lawn gently slopes towards a serene body of water in the distance, framed by tall trees on either side. The landscape features lush greenery under a partly cloudy sky, creating an open and inviting outdoor space.
Condo in Lake Geneva

Lake Geneva Cloud 9

Indoor spacesFamilyWi-Fi

4.98 out of 5 average rating, 259 reviews
Top Guest favourite
A decorative wall sign displays the word 'WELCOME' prominently. Beneath it, a white vase filled with yellow flowers adds a touch of color, set against a soft green wall, creating a friendly and inviting ambiance.
Home in Lake Geneva

Home away from Home

Indoor spacesKitchenBiking

4.93 out of 5 average rating, 174 reviews

When is the best time to visit Waukesha?

MonthJanFebMarAprMayJuneJulyAugSeptOctNovDec
Avg. price$232 AUD$236 AUD$199 AUD$222 AUD$249 AUD$278 AUD$384 AUD$330 AUD$270 AUD$270 AUD$273 AUD$267 AUD
Avg. temp-4°C-3°C3°C8°C14°C20°C23°C22°C18°C12°C5°C-1°C

Destinations to explore