Family-friendly vacation 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.

4.92 out of 5 average rating, 166 reviews

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.

A historic building is captured from street level, featuring a distinctive turret at the corner and elegant architectural details on the facade. Large windows allow natural light to fill the ground-level spaces, while trees softly frame the scene against a clear blue sky.

4.93 out of 5 average rating, 104 reviews

Historic downtown upstairs 2-bedroom rental unit

This apartment is located in the heart of downtown Port Washington with easy access to adorable shops, delicious restaurants, and the beautiful lakefront. It may be a small town but there are plenty of things to do. Rent a bike. Take a walk to the lighthouse. Get ice cream with the family. Or even take a thirty minute drive to Milwaukee. This historic unit sits above a hair salon that I have owned for the past 27 years. I've raised my three children in this cute town and would love to share it.

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 out of 5 average rating, 248 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.

A welcoming home exterior is shown with a well-maintained lawn and colorful flowerbeds. The facade features a combination of stone and siding, with large windows that allow ample natural light, and a covered entrance adds to the appeal.

4.96 out of 5 average rating, 138 reviews

Picturesque Port Washington-HomePort LLC

The apartment is the lower level of our home in picturesque Port Washington. Quiet neighborhood, close to parks and close to bike path. There is 1 parking space and a separate entrance in the back of the house. There is a double futon in living area, bedroom has a queen size bed and newly renovated bathroom with a large shower. We are located 2 miles west of downtown Port which has many quaint shops, restaurants and a marina offering many opportunities for outdoor recreation and relaxation.

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.

4.9 out of 5 average rating, 147 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!

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, 291 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.

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.

4.97 out of 5 average rating, 144 reviews

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.

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, 327 reviews

Grace Adventure House, walk to Port, Shops, Beach

Unleash Your Inner Explorer at Our Charming Cream City Brick Haven! Bring the whole crew - yes, even Fido! - to our delightful, sunlit two-bedroom upper flat, nestled just 4 blocks from the mesmerizing shores of Lake Michigan. Here, you'll find your escape from the hustle and bustle, stepping into a world where history whispers stories, warmth wraps around you like a cozy blanket, and charm invites you to unwind. A sanctuary of serenity and fun where every moment is a memory in the making.

4.96 out of 5 average rating, 162 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.

5 out of 5 average rating, 161 reviews

The cabin's exterior features a modern design with a dark green facade and a sloped metal roof. Large windows reflect the surrounding greenery, while a gravel pathway leads to the entrance, framed by vibrant foliage and a landscaped yard.

Cabin in Cascade

hot tub and sauna on 5 private acres

Need a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your inspired getaway awaits!

4.99 out of 5 average rating, 174 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.

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.