Family-friendly vacation rentals in Waukesha County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Waukesha County

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

Guesthouse in Richfield

4.94 out of 5 average rating, 254 reviews

Peaceful weekend or extended stay, full amenities

The Country Retreat at the historic Schmitz Family Farm is close to many attractions, ideal for couples, families, girls' weekends, extended stays, business travel, and is dog friendly. Enjoy a sunrise or sunset, get cozy at the fireplace, or indulge in the many activities our area has to offer. We feature two beautiful bedrooms, living room with two sleeper sofas (can also be used as a third bedroom, as door closes for privacy), laundry room, full kitchen, coffee nook, quiet deck and backyard.

Guest favorite

Home in Milwaukee

4.95 out of 5 average rating, 111 reviews

This Must Be the Place- Bayview Bohemian Vibes

Perfect for families! We have a cozy light filled home in a quiet walkable neighborhood of Bayview. Enjoy the back porch with a coffee or local brew. We are a 5 minute drive from the airport, 10 min to downtown Mke and 5 minute walk to public transit. Parks are in walking distance as well as cafes & restaurants. Our home is a great place for couples, solo adventurers, business travelers, families, groups, and furry friends (Fee of $150 up to two well behaved dogs) Relax, unwind & enjoy our home!

Top guest favorite

Apartment in Kenosha

4.93 out of 5 average rating, 243 reviews

Cheerful Apartment in Downtown Arts District

Cheerful apartment in newly renovated building above Professional Acting Studio at edge of Kenosha's Downtown Arts District. Near Harbor, beach, 4 museums, art galleries, live entertainment, eclectic restaurants, diners, coffee shops, Trolly, bike paths, parks, lakeshore, antique stores and specialty shops, Prime Outlets, Bristol Renaissance Faire, Great America. Metra Line to Chicago, close to Milwaukee. My place is good for couples, solo adventurers, business travelers, friends and families.

Superhost

Apartment in Milwaukee

4.83 out of 5 average rating, 272 reviews

Best location in Milwaukee! Lower Duplex Unit

LONG TERM STAYS WELCOME. Unit is right off Brady Street, One of the best streets in Milwaukee. Over 70 places to eat or drink within walking distance, including bars with free shuttles to brewers games and Summerfest. There are many shops and grocery stores in the neighborhood and everything you could possibly want is a short Uber ride away. Best enjoyed by up to six people whether they be couples, friends, solo adventurers, business travelers, families (with kids), and furry friends (pets).

Guest favorite

Cabin in Elkhorn

4.97 out of 5 average rating, 298 reviews

The Retreat: 5 Acre Log Cabin

Escape to this beautiful 5-acre country retreat, located a short drive from Lauderdale Lakes, Alpine Valley, and Lake Geneva. The cabin features two kitchens, two family rooms, a year around hot tub, a game room, an arcade, and five bedrooms with comfortable king-sized beds. The master suite also includes a steam room for added luxury. Spend your days enjoying the great outdoors with a game of beach volleyball or roasting marshmallows around a bonfire, while taking in the fresh midwestern air.

Guest favorite

Guesthouse in Elkhorn

4.98 out of 5 average rating, 166 reviews

Camp Wandawega: Lakeside 3 Bedroom Cabin

Overlooking the lake nestled right behind the main lodge, this cabin has 3 bedrooms, a half bathroom, a seating a room, a basic kitchenette & access to camp showers downstairs. One large bedroom has a queen bed, one room with bunkbeds, & one with a full bed to accommodate a max of 6 guests. (But the bunkbeds are best for kid-sized humans). Like all of Wandawega, it’s a back-to-basics, no-frills, primitive experience. Simple rooms, vintage furnishings. There is heat & a couple AC window units.

Superhost

Home in Kenosha

4.92 out of 5 average rating, 272 reviews

Where Family & Friends Gather to Create & Remember

Come gather, relax & celebrate at our 1 acre estate near beaches, dining & Carthage College! The designer interior features 5 BR/4 Bath, chef's kitchen with Viking & Subzero, Coffee/Espresso Bar, dining area for 12, 2 spacious family rooms with piano, fireplace and TVs. Enjoy dining, lounging & fun in the great outdoors w/hot tub, fire pit, basketball, pickleball, ping pong & lawn games! Beaches are walkable under a mile & near lively downtown w/ harbor, restaurants, shopping & museums.

Top guest favorite

Apartment in Lake Geneva

5 out of 5 average rating, 241 reviews

Downtown Geneva Street Getaway

Geneva Street Getaway is one block from downtown and 2 blocks to the beach!! The unit consists of the entire, private first floor. It has 2 bedrooms (1 king- 1st and 1 queen -2nd) 2 full bathrooms, 2 common areas with sleepers (queens with gel memory foam mattresses), and a kitchenette, to accommodate 8. The décor is tasteful, bright, and airy. Licensed and approved by the city, our comfortable home is within steps of downtown restaurants, bars, shopping, boat rentals, and the beach!

Guest favorite

Home in Williams Bay

4.95 out of 5 average rating, 332 reviews

Williams Bay House - 1 Block to Geneva Lake

The home was featured in the Experience Wisconsin Magazine article "The Six Coolest Airbnbs Found in Wisconsin". We look forward to providing a relaxing retreat with excellent service for our guests. The Williams Bay House is located in downtown Williams Bay, Wisconsin, about 1 block from Geneva Lake. Walk to the beach, boardwalk, boat launch, nature conservancy, park, restaurants, and shops. We offer flexible check-in and check-out times. The primary guest must be over the age of 25.

Guest favorite

Home in Racine

4.94 out of 5 average rating, 156 reviews

Root River Home - Waterfront property - Sleeps 8+

Beautiful waterfront escape awaits you. Located along the Root River, Village of Caledonia, WI (Racine County) 10 Minutes / 3 Miles from North Beach (Lake Michigan) and only 5 minutes from Quarry Lake Park (Swimming and Recreation Area). Includes Kayaks, Canoes, Row Boat, Paddle boat, Firewood, Gas Grills, Netflix, WIFI, TV, and Wi and Playstation for the Kids, Ping Pong Table, outdoor firepits and much much more.

Superhost

Home in Milwaukee

4.76 out of 5 average rating, 140 reviews

Peaceful home in beauitful Bayview!

Enjoy the best that Bay View has to offer! Located in a quiet neighborhood just blocks from the lakefront and Kinnickinnic Ave, lined with cafés, restaurants, and bars, this modern and spacious house is the perfect home away from home. Fully furnished kitchen, finished basement, back patio, washer/dryer, office den. Pets considered. 10 minute drive from downtown or the airport.

Guest favorite

Apartment in Fort Atkinson

4.95 out of 5 average rating, 249 reviews

‘The Part Time Local’ - A boho small town retreat.

A cozy, comfortable 1 bedroom apartment with eat in kitchen and separate living room. Newly remodeled bathroom with tiled shower. Mahogany floors and all the charm you'd expect in a 1907 Arts & Crafts. Stylish, boho décor to make anyone feel right at home. Private balcony with Rock River views. Laundry available. Downtown Fort Atkinson, walking distance to everything!