Family-friendly vacation rentals in Port Washington

4.94 out of 5 average rating, 254 reviews

A charming red farmhouse is set against a colorful sky at sunset, surrounded by a picturesque yard filled with wildflowers. The property features a wooden fence and mature trees, contributing to a serene rural atmosphere.

Guesthouse in Richfield

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.

4.95 out of 5 average rating, 111 reviews

Home in Bay View

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!

4.89 out of 5 average rating, 231 reviews

The exterior of the home features a stately design with prominent arched windows and a welcoming entrance. Lush greenery surrounds the property, while the evening sky casts a warm glow, enhancing the peaceful ambiance of the space.

Home in Walker's Point

Historic Home Sleeps 16 in MKEs Best Neighborhood

MAX of 16 guests! This luxury home has been designed especially for groups to gather and connect in-person. The huge second floor has ample space to gather everyone around a chef's kitchen and walk-out patio, while floors 1 & 3 are for sleeping Walk or bike everywhere! Minutes to Downtown, Third Ward, Bay View, Summerfest, and the best restaurants, breweries, trails, and music/sports venues. Just 5 blocks from easy freeway access and 12 minutes from airport! 2 driveway parking spots included

4.98 out of 5 average rating, 125 reviews

The two-story home features a beige exterior with multiple windows, surrounded by a grassy yard. Two chairs are positioned in front on a small patio area. Large trees provide shade, while a view of the countryside and other structures is visible in the background.

Home in Glenbeulah

Stay at Sunrise LLC, Like being at Grandma's

Welcome to Stay at Sunrise LLC. We offer a clean and comfortable home for your vacation enjoyment. We are in a rural area, recreation trail head is 3 miles east of us as is the Wade House, 7 miles from Road America. Large yard, Fire pit, picnic table, child swing set. Garage parking on site if arranged in advance. We do not have WIFI Phone reception for Internet is good. No Cable or Satellite TV, Over 32 antenna channels. Smoking is allowed outside of the home. No pets allowed.

Apartment in Lower East Side

A comfortable living area is furnished with a brown sectional sofa and a wooden coffee table, displaying decorative items. A colorful area rug enhances the space. The walls feature a map design in various colors, adding character. An archway leads to a bedroom area in the background.

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).

4.97 out of 5 average rating, 116 reviews

A red cottage is nestled among lush green trees, with a winding driveway leading to its entrance. Steps ascend to the upper level, and patches of sunlight filter through the leaves, highlighting the natural surroundings.

Guesthouse in Plymouth

Woodside Cottage Guest House-Close to Road America

Woodside Cottage in the Kettle Moraine forest of East Central Wisconsin offers a quiet private getaway for Road American race fans, golfers or those wanting just to have a break from the city and explore the area. This 2 bedroom guesthouse can host 8, with laundry, full kitchen, living room and outdoor fire pit. Due to family guest allergies, we are pet free. Located 4 miles from gate 4 at Road America and 20 miles from Whistling Straits golf course. WIFI available, but unreliable. 3 cars MAX

4.95 out of 5 average rating, 144 reviews

A modern single-story home features a light gray exterior with a striking yellow front door. Large windows provide abundant natural light, while a well-maintained lawn is complemented by colorful flower beds. Skylights on the roof enhance the home's contemporary design.

Home in Cleveland

Modern Home Just 40 Minutes from GB NFL Draft

My home is just minutes from Whistling Straits Golf, Road America, Lake Michigan, Parks, Hiking, Biking, Snowshoeing, and Cross Country Skiing. You’ll love my place as it's newly remodeled, modern & cozy. The kitchen and living areas have high ceilings, sky lights & new furniture. The large outdoor living area is perfect for social time. My favorite is the heated bathroom floors. My place is perfect for golfers, wedding groups, couples, business travelers, and families (with kids & dogs).

4.83 out of 5 average rating, 101 reviews

A bright living room features two lightweight armchairs, a round coffee table, and a comfortable sofa with neutral tones. Natural light fills the space through a large window, enhancing the ambiance. A ceiling fan hangs above, and a world map artwork adds a touch of style.

Home in Cudahy

Wonderful Family Home Across from Park

Extended Stays Welcome! Everything you could want in a home away from home. Our place is a comfortable and beautifully updated mid-century brick ranch on a quiet tree-lined street overlooking 36-acre Greene Park. Super convenient location, just 10 min from both the airport and downtown. Walkable to Lake Michigan and just down the road from Bay View's great restaurants and nightlife. Pet-friendly and perfect for families, small groups, or business travel. You'll feel right at home here!

4.94 out of 5 average rating, 196 reviews

Home in Sheboygan

Beachfront getaway in Sheboygan

One of the few homes in Sheboygan that walks out onto the sands of Lake Michigan, this 3 bedroom/ 2 bath home is meant for total relaxation and fun. The open kitchen, dining and living room is full of light from the sliding glass doors on the back of the house, which access a deck and a large back yard. Upstairs is a spacious loft with a pull out couch. Fire pit in the back yard. Just steps from a playground at King Park. Amazing sunrises, worth waking up for.

4.96 out of 5 average rating, 187 reviews

An outdoor deck features a dining table surrounded by chairs, with a large umbrella providing shade. Beyond the deck, sandy beach and gentle waves of Lake Michigan can be seen, framed by tall grasses, creating a serene coastal atmosphere.

Home in Oostburg

Shamba on the Lake, Oostburg, WI

Large guest home , in a rustic setting, on a peaceful 2-acre wooded lot (only 5 homes on a very private road) on Lake Michigan with a large private beach a few feet from the deck. . Magnificent panoramic view, amazing sunrises, serene twilights, magical star-studded night skies. A slice of Paradise you must experience. Located a mile from I43, 40 minutes from downtown Milwaukee, 20 mins. from golf courses in Kohler, 30 mins. from Road America in Elkhart Lake...

4.99 out of 5 average rating, 282 reviews

A relaxing living area features a stone fireplace as its focal point. Comfortable seating options, including a leather chair and a spacious sofa, are arranged around a rustic coffee table. Large windows allow natural light to fill the space, with glimpses of the surrounding scenery.

Cottage in Fond du Lac

Beautiful Lake Home.

Our Beautiful two bedroom cottage is located on the shores of Lake Winnebago . Centrally located to many of Wisconsin's best attractions. Less than 1 hour from Milwaukee, Madison, Green Bay, Close to Oshkosh (EAA) and Elkhart Lake. Includes 2 bedrooms, with plush queen beds, 1 full bathroom, Laundry room with washer and dryer. The perfect home for a laid back group of friends, couples or a family to stay with all the comforts of being at home.