Family-friendly holiday rentals in Port Washington

Townhouse in Port Washington

A two-family home is displayed, featuring a mix of siding and vibrant red vines cascading over its exterior. The front porch is visible, leading to the entrance, while flowers bloom along the base, adding a touch of color to the surroundings.

Near Lakefront and Downtown

Steps from picturesque downtown Port Washington and all the amenities available. Close to the action, but not too close. Restaurants, bars, shopping, the lakefront and marina, charter fishing, beaches, festivals, winery, brewery, beer garden, etc. are just a few of the things available to you in this quaint town which has been called the Cape Cod of the Midwest. Enjoy the entire lower level of this lovingly restored two-family home. Close driving distance to other historic areas like Cedarburg.

FamilyKitchenAir conditioning

4.91 out of 5 average rating, 206 reviews

4.99 out of 5 average rating, 111 reviews

A cozy living area features a large brown sectional sofa adorned with patterned cushions. Windows allow natural light to flood in, showcasing views of the outdoors. A round wall clock hangs above, and a small wooden bench complements the inviting space.

Apartment in Cedarburg

Perfect Balance in Cedarburg Gem

This spacious, private studio apartment offers a perfect blend of serenity and activity. Situated at the back of a 1.25 acre lot, beyond the lovely 1862 stone farmhouse it overlooks, the carriage house is a peaceful getaway -- minutes from all that bustling historic Cedarburg has to offer. Just .4 mile from the OZA Fairgrounds and .8 mile to downtown shops and restaurants, it's a quick drive or an easy walk to many amenities. Relax on the balcony before or after a day of fun sightseeing. Cheers!

KitchenIndoor spacesTV

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.

5.0 out of 5 average rating, 272 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.

FamilyIndoor spacesAmenities

The kitchen features a granite countertop with a stainless steel sink, complemented by white cabinetry and a decorative rug. Shelves display colorful dishware, and a doorway leads to the adjoining living spaces.

4.89 out of 5 average rating, 180 reviews

Lighthouse View -a real gem on Sweet Cake Hill

Enjoy the view of the Port Washington Lighthouse, Marina, and Lake Michigan from your private 1 queen bedroom (plus 2 futons in Living room) upper bungalow apartment. Our house was built in 1900 it has older architectural features. Please look at all the pictures. Private entrance, bathroom, and kitchen with range and refrigerator. Living room has plenty of seating and smart TV. Two block walk to the downtown with 17 restaurants and pubs within walking distance. Only 3 blocks to the marina!

KitchenIndoor spacesHeating

A book titled 'Silvers' with the subtitle 'Guests Four Six Four' is displayed against a tan textured background. The phrase 'try something new, you may like it' is printed below the book in a casual font.

4.95 out of 5 average rating, 324 reviews

Silvers Four-Six-Four *A home away from home*

An upper flat in walking distance from downtown Port Washington's restaurants, pubs, and summertime live music events. Walk and enjoy Lake Michigan's beaches, pier, and parks. A half block off of the interurban bike and running trail. Spacious apartment boasting a light, fresh, clean and airy feel. Plenty of room to help you feel at home. There is off road parking and a fenced in yard to park bikes or motorcycles. A garage is also available upon request when making your reservation.

Indoor spacesFamilyValue

Bungalow in Port Washington

The exterior of the bungalow is showcased, featuring multiple large windows and a front porch adorned with flowering plants. A well-maintained lawn surrounds the home, while trees provide greenery, enhancing the overall inviting appearance of the property.

Helena House Port Washington, Lake Michigan View

The Helena House is a charming renovated 1913 Bungalow that features 2 main level bedrooms & bath with a handicap accessible shower, and fully furnished kitchen. The second level is a new spacious master ensuite. Relax on the front porch as you enjoy a view of Lake Michigan. Our home is a couple minute walk to the lake, downtown, restaurants, and shopping. A short 30-minute drive to downtown Milwaukee and 30 miles south of Kohler. The Interurban Trail is easily accessible from our location.

Indoor spacesFamilyValue

4.96 out of 5 average rating, 169 reviews

4.96 out of 5 average rating, 183 reviews

An aerial view of a spacious home is surrounded by mature trees, showcasing a private sandy beach alongside Lake Michigan. The property features a pathway leading to the house, emphasizing its secluded setting amid natural greenery.

Home in Oostburg

Lake Michigan Beach Home by Frank Lloyd Wright pro

Beautiful view and sand beach on Lake Michigan, completely private, surrounded by mature white pine trees and cedar trees. The spacious home is fully equipped with an "eat in" kitchen, dining room, and living room entertainment space, den with a see-through log-fired fireplace, screened-in porch to accommodate additional eating space, large outdoor deck with grill and fire pit. A canoe and a row boat are available for the boating enthusiast, with life jackets and other floating devices.

Indoor spacesFamilyNearby

4.99 out of 5 average rating, 201 reviews

A comfortable living space is presented, featuring a cozy sofa with decorative cushions. A glass table with three small potted plants sits in the foreground. Natural light enters through the large windows, framing a view of the greenery outside.

Loft in Port Washington

Cozy Carriage House Loft – Walk to Lake & Downtown

Relax in this cozy Carriage House Loft, tucked in the heart of historic Port Washington. Just a mile from Lake Michigan, sandy beaches, the iconic lighthouse, marina, and the charming downtown with local dining, coffee shops, and boutique shopping. This private retreat has its own entrance and is set in a quiet neighborhood, giving you the ideal mix of seclusion and accessibility. You’re only a 30-minute drive to downtown Milwaukee, and a scenic 30 miles south of Sheboygan and Kohler.

KitchenFamilyGetting around

The exterior of a two-story home is shown, featuring a beige facade with white trim. A red door adds a pop of color, and flower boxes are mounted under the front windows. In the background, a clock tower is visible, indicating proximity to local attractions.

4.98 out of 5 average rating, 228 reviews

Inn on Billy Goat Hill

Come enjoy our upper 2-bedroom apartment in charming Port Washington filled with personal, welcoming touches. We live in a quiet neighborhood on Billy Goat Hill, which overlooks the downtown. The location is very walkable and close to fishing, swimming, boating, biking, shops, pubs, farmers' market, homemade ice cream , and historical sites of interest. We live downstairs and often will be here if you have any needs or concerns, but are very conscious of your desire for privacy.

KitchenIndoor spacesSleep quality

4.86 out of 5 average rating, 118 reviews

The exterior of a spacious lakeside home is showcased, featuring large windows and a welcoming porch. A green lawn extends towards the water, accompanied by bright blue kayaks and a swing set. A tall tree provides shade, enhancing the outdoor ambiance.

Cottage in Random Lake

Private 3 bedroom lake house

A beautiful spacious 3 bedroom with sofa bed (sleeps 9 guests) with lake access just steps away from the backyard. Includes washer and dryer, all cooking amenities and a grill, 3 TVs with cable (including Netflix and Disney+ capabilities), a two person canoe n 3 kayaks, hammock, board games, and books for leisure reading. Fish off the private peer. Light the bonfire in the fire pit (firewood included) by the patio onlooking the lake. Pets are allowed with a $200 pet fee.

Indoor spacesFamilyNearby

4.98 out of 5 average rating, 241 reviews

The exterior of a single-family home is presented, showcasing a welcoming yellow facade with blue shutters. A white porch with steps leads to the entrance, complemented by neatly trimmed shrubs and a grassy area. An American flag adorns the porch, enhancing the inviting appearance.

Home in Cedarburg

Our Happy Place in Cedarburg

You are certain to enjoy a special gathering with family or friends at Our Happy Place. Three bedroom / two bathroom single family home has all the conveniences of home. The property is just a one block stroll from many of the unique festivals held in historic downtown Cedarburg. Three wineries, numerous restaurants, coffee shops and fun shopping all within short walking distance. Friendly, safe neighborhood with quiet sleeping areas inside.

FamilyIndoor spacesLayout

A spacious dining area features a large wooden table surrounded by eight wooden chairs. A decorative chandelier hangs overhead, while a vibrant painting and ornate mirror enhance the ambiance. A decorative area rug covers the floor, and a vintage radiator is visible in the background.

4.96 out of 5 average rating, 344 reviews

Grace Adventure House, Family Friendly, Sleeps 8

Welcome to Grace Adventure House – your ultimate family-and-dog-friendly vacation rental in charming Port Washington, Wisconsin. Just 4 blocks from sparkling Lake Michigan and vibrant downtown Port Washington, this beautifully restored 1865 Cream City Brick upstairs apartment is your peaceful, luxurious escape. Think storybook vibes meets modern comfort – the perfect Lake Michigan getaway for families, couples, and kids alike.

KitchenFamilyLaundry

Popular amenities for Port Washington family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.88 out of 5 average rating, 531 reviews

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

FamilyKitchenLayout

5.0 out of 5 average rating, 281 reviews

Cabin in Cascade

hot tub and sauna on 5 private acres

FamilyIndoor spacesOutdoor spaces

4.97 out of 5 average rating, 149 reviews

The cabin is set against a vibrant sunset, showcasing a spacious deck surrounded by lush greenery. Stone accents and floral arrangements enhance the outdoor space, while large windows reflect the warm light of the evening sky.

Cabin in Waterford

5 bed/3 bath cabin SE WI 1hr fr Chicago! Sleeps 16

Indoor spacesKitchenOutdoor spaces

4.93 out of 5 average rating, 301 reviews

A rustic modern home is showcased, featuring a spacious wraparound deck surrounded by lush greenery. An inviting hot tub glistens in the sun, and an arcade room with various games is displayed, offering entertainment options for guests.

Home in Elkhart Lake

The LODGE in Elkhart Lake. —-Hot Tub & Arcade—-

FamilyKitchenCleanliness

4.99 out of 5 average rating, 178 reviews

Castle in Cleveland

Stay in a Real Castle on a Vineyard

KitchenIndoor spacesLocation

5.0 out of 5 average rating, 316 reviews

A hot tub is positioned on a wooden deck with a view of a fenced backyard, featuring charming seating areas surrounded by lush greenery. Potted plants line the space, and a geometric-patterned rug adds a pop of color beneath outdoor furniture.

Home in Wauwatosa

The Little Gray House

KitchenFamilyEV charging

4.92 out of 5 average rating, 132 reviews

A historic lighthouse stands at the water's edge, illuminated by the vibrant colors of sunset. Smooth stones line the shoreline, reflecting the serene lake. Lush greenery is visible in the background, creating a peaceful coastal setting.

Home in Fond du Lac

Woltring Waters Waterfront Home + Hot Tub

FamilyIndoor spacesHospitality

4.95 out of 5 average rating, 114 reviews

Home in Milwaukee

Brew City Inn with Hot Tub | Summerfest House

FamilyIndoor spacesNearby

Family- and pet-friendly home rentals

Superhost

Guest suite in Cedarburg

A Great Stay in A Great City

Indoor spacesKitchenBathroom

4.82 out of 5 average rating, 344 reviews

4.94 out of 5 average rating, 590 reviews

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 spacesFamilyLong stay

4.96 out of 5 average rating, 192 reviews

A red barn stands prominently amid a snowy landscape, bordered by lush green grass. A tree casts a shadow, and a silos is visible to the left. A gravel path leads to the barn, while a white fence outlines the property in the background.

Guesthouse in Hubertus

Quiet retreat-golf, bike, hike, motorcycle

KitchenFamilyWi-Fi

4.98 out of 5 average rating, 165 reviews

A cozy living area is filled with neutral-toned furniture, including a large sofa, accent chairs, and a circular coffee table. Natural light filters in through large windows, highlighting the wooden floors and a decorative area rug beneath. Soft green accents are present in the lamps and curtains.

Home in Sheboygan

House Near the Lake

KitchenFamilyHospitality

4.98 out of 5 average rating, 323 reviews

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

The Blue Cobb House

Indoor spacesFamilyView

4.98 out of 5 average rating, 129 reviews

A two-story brick building houses a coffee shop on the ground floor, featuring large windows flanked by a striped awning. The entrance is highlighted by a sign that announces it as Kettle Moraine's Favorite Espresso Bar. A welcoming atmosphere is created by its corner placement and outdoor seating area.

Apartment in Kewaskum

Local Landmark CF / Artisan Coffeehouse

KitchenIndoor spacesTV

4.95 out of 5 average rating, 305 reviews

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

Peaceful weekend or extended stay, full amenities

Indoor spacesKitchenBarbecue

4.98 out of 5 average rating, 220 reviews

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

Indoor spacesFamilyCheck-in

Family-friendly home rentals with a pool

Earthen home in Elkhart Lake

Secluded Elkhart Retreat | Pool, Hot Tub & Sunset

KitchenFamilyCleanliness

4.97 out of 5 average rating, 158 reviews

4.93 out of 5 average rating, 135 reviews

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

KitchenFamilyTV

4.97 out of 5 average rating, 122 reviews

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

KitchenIndoor spacesOutdoor spaces

4.92 out of 5 average rating, 197 reviews

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

FamilyIndoor spacesBathroom

4.87 out of 5 average rating, 708 reviews

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 spacesHospitality

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!

KitchenFamilySkiing

4.77 out of 5 average rating, 168 reviews

Superhost

A white motor yacht, named 'Irish Mist,' is docked at Reefpoint Marina. The boat features a spacious top deck with a black canopy and is surrounded by other yachts in the water, with a soft sunset glow illuminating the scene.

Boat in Racine

Vessel: Irish Mist V - 32' @ Reefpoint W1-3

KitchenFamilyRiver

4.81 out of 5 average rating, 145 reviews