Family-friendly vacation rentals in Port Washington

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Top-rated family-friendly rentals in Port Washington

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

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Top guest favorite

A charming red farmhouse is set against a snowy landscape, surrounded by a white fence. Leafless trees create a serene backdrop, enhancing the rural setting. The house features a mix of traditional and modern architecture with snow covering the yard.

Guesthouse in Richfield

4.94 out of 5 average rating, 257 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.

Superhost

A charming brick house is surrounded by well-maintained landscaping, featuring various green shrubs and white flowering plants. The front yard offers a neat lawn and a flower bed with stones. The adjacent houses are visible, showcasing a friendly neighborhood vibe.

Guest suite in Bay View

4.81 out of 5 average rating, 114 reviews

Basement Bay View Suite,express bus airport-north

Bay View is a walking community. Our place is close to family-friendly activities, public transport, & the airport. You’ll love our place. It's a short walk to express bus from airport, past downtown, UW-M and to Bayside. Located across the street from Humboldt Park. We are about a 20 minute walk from Lake Michigan. Summerfest grounds a short bus ride away. Winter is fun in the park. Tobogganing (2), skates and cross country skis to use. Hope the sizes fit you. I find if one plays in snow ⛄️ 😌

Top guest favorite

The front exterior of the duplex showcases a charming farmhouse style with light grey siding and white trim. Two levels of porches with railings are complemented by doorways in vibrant turquoise. Flower baskets hang from the porch beams, and a garden with greenery enhances the inviting atmosphere.

Apartment in Port Washington

5 out of 5 average rating, 237 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.

Top guest favorite

A cozy living area features a soft sofa adorned with colorful cushions, complemented by an accent chair. A stylish glass coffee table sits atop a geometric-patterned rug. Natural light filters through two windows, enhancing the warm ambiance of the space.

Townhouse in Bay View

4.95 out of 5 average rating, 415 reviews

Vintage Bay View - Big Backyard, Big 1 Bedroom

Welcome to your Milwaukee getaway! Located in the Bay View area, you're walking distance from the best farm-to-table restaurants, music venues, art fairs, and craft beer in the city. Not only that, but Lake Michigan's beaches, Miller Park, and downtown are a short drive away. The location is ideal. The place was created with a 70's midwestern feel, with wood-paneled furniture pieces and mod design. It also boasts a giant kitchen and backyard with grill. We can't wait for you to visit!

Guest favorite

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, 291 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 favorite

Tall sunflowers bloom vibrantly in a garden, displaying bright yellow and orange petals. A wooden gazebo with hanging lights stands in the background, surrounded by lush greenery. Soft sunlight filters through the trees, enhancing the serene outdoor setting.

Guest suite in Sussex

4.99 out of 5 average rating, 142 reviews

Garden Retreat in law Suite

Welcome to our in-law suite apartment featuring a full eat-in kitchen, living room, queen bed in large bedroom, walk in closet and full bathroom with walk-in shower. Our beautiful two acre yard has many areas to relax in, including a hammock and fire pit for the evenings. Twenty mins. to Erin Hills and Holy Hill and a half hour to most downtown Milwaukee attractions, as well as the RNC activities taking place this summer. Lots of city tips and suggestions for our guests.

Guest favorite

A tranquil view of Lake Michigan at sunset, where calm waters reflect soft hues of orange and pink. The sky showcases wispy clouds, and a distant bird is seen soaring above the serene landscape, creating a peaceful setting.

Home in Sheboygan

4.94 out of 5 average rating, 199 reviews

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.

Top guest favorite

A quaint living space features an antique-style fireplace made of dark wood, with a circular mirror above it. A flat-screen television is mounted on the wall opposite a small table and a suitcase rests on the hardwood floor, accompanied by a decorative flower arrangement.

Apartment in Waldo

4.98 out of 5 average rating, 279 reviews

The Blue Cobb House

My place is close to 20 minutes south of Elkhart Lake and Road America. You’ll love my place because of the outdoors space, the comfy bed, and the kitchen. My place is good for couples, solo adventurers, and business travelers. The Blue Cobb House is about 15 minutes from Kohler-Andrae State Park and 30 minutes from Harrington Beach State Park. The Kettle Moraine area is just to our west and it is filled with hiking trails.

Guest favorite

A spacious living room features a large gray sectional sofa, an armchair in burgundy, and a dark wood TV stand with a flat-screen television. Natural light enters through the window, complemented by light-filtering shades. A neutral wall displays a framed cityscape artwork.

Apartment in Riverwest

4.83 out of 5 average rating, 149 reviews

Mid-century Lower in Riverwest

This 2 BR duplex lower apartment is located in Milwaukee's Riverwest neighborhood, 2 miles directly north of downtown. It is furnished with many vintage mid-century furnishings, including a working HiFi. There is a garage space for your use during your stay, and ample street parking right in front making it easy to come and go. The kitchen has dishes, pots, pans, and all the utensils you will need during your time here.

Top guest favorite

A warm and inviting bedroom is framed by sliding barn doors, revealing a spacious bed with white bedding. Two bedside tables, each adorned with a lamp, provide light. Natural light enters through two windows, accentuated by wooden trim and classic blinds.

Apartment in Kohler

4.99 out of 5 average rating, 140 reviews

Washington Walk Historic House w/elegant spa bath

This 1880's Historic Riverside Tavern was completely remodeled in 2017, maintaining as much of the original character as possible. The Village of Kohler moved the building to its' current location in 1908 - eventually closing the tavern to establish the Kohler Women's Club in the 1920s. It opened with a tea room on the first floor as well as the upstairs being home to the original Kohler Girl Scouts.

Guest favorite

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

4.96 out of 5 average rating, 539 reviews

Hugel Hutte - Log Cabin Getaway

Welcome to the Hugel Hutte! This cute little cabin is perched on the hill top. It's feels like a tree house! You have the kitchen to use, but the famous Fox & Hound's restaurant is just steps away. It's literally right next door. So grab a few drinks and dinner...and walk home to your cabin retreat for the night. Enjoy the tranquil naturescape surrounding the house.

Top guest favorite

A comfortable leather sofa with patterned cushions is positioned in the living area. A wooden cabinet with glass doors displays decorative items. The room features a colorful area rug and walls that are partially adorned with wooden accents, contributing to a cozy ambiance.

Apartment in Port Washington

4.93 out of 5 average rating, 298 reviews

Homeport

The apartment is a remodeled former "Summer Kitchen" in the lower level of our cream city brick home. We are located in the heart of downtown next to the marina, close to parks, steps away from restaurants, coffee shops & bars. Lake Michigan is just outside the door! We invite couples, solo adventurers, and business travelers for short and long-term stays.