Family-friendly vacation rentals in Waukesha County

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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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Guest favorite

Cottage in Richfield

4.95 out of 5 average rating, 245 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

Rental unit in Port Washington

5 out of 5 average rating, 224 reviews

Beautiful Port home short walk to town and lake

Enjoy Grace Guest house and the sights and sounds of Port Washington at our bright turn of the century duplex. Your private upstairs unit has 1.5 baths, a full kitchen and 3 bedrooms. Freshly renovated, our 1890 home is sure to charm with its many original features and large modern bathrooms and kitchen. Your second floor private walk-out deck is a great place to enjoy a morning coffee or cocktail and take in the Lake View. Port Washington’s shops and restaurants are a quick 4 minute walk.

Guest favorite

Cabin in Elkhorn

4.97 out of 5 average rating, 278 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

Rental unit in Lake Geneva

4.98 out of 5 average rating, 872 reviews

Geneva Street Inn in Maple Park Historic District

Geneva Street Inn is located one block away from the heart of Lake Geneva. This beautiful 1890's home is appealing to everybody whether your stay is a business trip, family, or even a couples getaway. A huge backyard and a front porch that will make you never want to leave. We strive to make your stay your "home away from home" with unique decor and it's timeless charm! Our price is inclusive cleaning fees (unless extenuating circumstances warrants a fee). We meet our guests at check-in.

Guest favorite

Guest suite in Sussex

4.97 out of 5 average rating, 268 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.

Superhost

Rental unit in West Allis

4.79 out of 5 average rating, 290 reviews

Kegel's Inn - Studio - Classic Apartment #3

Quaint little studio with lots of old-world character. This one-room studio has original hardwood floors, heavy wood ceiling beams and 1930's tile work in the bathroom. The apartment looks down on 59th street, which for the summer months between May and November, hosts the Kegels Beer Garden on the street! We're one of the last Authentic German restaurants and Inn's left in country and the studio apartment is right above it! We hope you love this place as much as we do!

Guest favorite

Rental unit in West Allis

4.91 out of 5 average rating, 293 reviews

The Cheese House

Large well appointed two bedroom, living room, dining room, kitchen, and private balcony. Apartment is located on the second floor right above the award winning West Allis Cheese & Sausage Shoppe. Each stay includes 4 breakfast sandwiches and house coffee vouchers for the cheese store cafe. The rental is centrally located minutes from Pettit National Ice Center, Milwaukee County Zoo, Wisconsin State Fair, and Brewers Stadium not to mention local restaurants.

Guest favorite

Rental unit in Racine

4.92 out of 5 average rating, 265 reviews

WAVES : Steps to the Harbor ~ Crash Here!

Welcome to "Waves Apartment," your ideal retreat by the harbor. This cozy apartment offers three queen-sized beds, two baths, and conveniences like onsite parking and a private deck. Enjoy the comfort of three bedrooms, two baths alongside an open living/dining area with scenic lake and harbor views. The fully equipped kitchen and laundry facilities ensure a hassle-free stay. Experience a blend of comfort and convenience, designed for your enjoyment.

Guest favorite

Home in Racine

4.94 out of 5 average rating, 150 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.

Guest favorite

Cabin in Kenosha

4.81 out of 5 average rating, 591 reviews

Lake Michigan Writer’s Cabin

Beautiful Lake Michigan retreat perfect for relaxing, boating, fishing, swimming and more! Fully remodeled. Perfect for ice fishing in the winter. A Sportsman’s paradise. Ideal for the adventurous. Relax, do some writing or work overlooking the breathtaking scenery. A stone's throw to the beach. Two decks overlooking the tranquil landscape. A short walk to downtown shops, cafes and restaurants.

Guest favorite

Guest suite in Helenville

4.94 out of 5 average rating, 356 reviews

Chic Loft Surrounded by Nature

This charming shabby chic loft sits in the heart of the country between Madison and Milwaukee. The Lighthouse Farm is also a wedding/event venue (please inquire for more details) . A quiet relaxing environment, with lots of open space, natural sunlight and lush green landscape. Great for those looking to get away with easy access to metropolitan areas, lakes, rivers and hiking/biking trails.

Guest favorite

Rental unit in Fort Atkinson

4.95 out of 5 average rating, 236 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!