Holiday houses in Milwaukee County

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Top-rated holiday rentals in Milwaukee County

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Guest favourite
A spacious back yard overlooks Lake Michigan, featuring a manicured lawn and five comfortable seating options. Sailboats are visible on the water, with a breakwater in the distance. The serene setting is framed by lush greenery, inviting relaxation and enjoyment of the scenic view.
Apartment in Bay View

Lakeside Beauty

Stunning lower duplex on Lake Michigan in beautiful Bay View WI. Exceptionally large 2 bedroom unit boasts back yard overlooking Lake Michigan with fire pit for cozy evening fires. Unit is a mix of new and classic vintage. Walking distance to South Shore Yacht Club, South Shore Terrace Beer Garden, Award Winning restaurants, a unique European grocery store, and the second largest Farmer's Market in the state. Seven minutes to downtown Milwaukee. Owner lives upstairs. Two bikes available.

4.86 out of 5 average rating, 319 reviews
Guest favourite
A cozy living space features a floral-patterned couch accompanied by a wooden coffee table. The walls are adorned with warm wood paneling, complemented by soft lighting from a wall sconce. Greenery is present with potted plants, adding a touch of nature to the space.
Home in Oak Creek

Spacious Ranch Home Oak Creek close to Airport

Chalet style ranch home is fully furnished and offers 2400 square feet of private usable space. The 3 bedrooms, living room, dining room, family room, 1 1/2 bathrooms, kitchen, and kitchen table area are all located on one floor. You will love waking up in the morning in this quiet suburban neighborhood and looking out the many windows at the park across the street. Close to the heart of Oak Creek Drexel Town Square, 4.6 miles from the airport, & 15 minutes from Downtown Milwaukee.

4.87 out of 5 average rating, 112 reviews
Top Guest favourite
Guest suite in South Milwaukee

Historic Hawthorne House

Nestled just steps from Grant Park Beach & Lake Michigan, the scenic Seven Bridges Trail, and the lush Grant Park Golf Course, this unique rental offers a blend of history, charm and comfort. Only a 10 minute drive to Mitchell International Airport and an easy 20 min drive to downtown Milwaukee. Whether you're here to unwind in nature, explore the local parks, enjoy a peaceful lakeside stay, or enjoy the best that Milwaukee has to offer this home has everything you need.

4.99 out of 5 average rating, 104 reviews
Guest favourite
Home in Bay View

Renovated 2-bed flat w/patio in heart of Bay View

Welcome to the heart of Bay View! This lower unit is newly renovated to have a modern interior while still offering the history of a house built in 1895. It's located on a low-traffic street that offers ample parking and a backyard patio, perfect for enjoying a beer from one of the local breweries. This unit consists of two bedrooms, a full bath, a full kitchen and a large common area. Come stay with us and find out why Bay View is the best neighborhood in Milwaukee!

4.9 out of 5 average rating, 101 reviews
Top Guest favourite
A well-equipped kitchen features white cabinetry, stainless steel appliances, and green tile backsplash. The space is illuminated with recessed lighting and includes a dining area with a wood table. An open doorway leads to another room, enhancing the overall flow of the layout.
Home in Shorewood

Shorewood house - near shops w/ WiFi & parking

Just down the road from Lake Michigan, this charming duplex upper is the perfect space for a relaxing getaway. After a day of shopping, eating good food, and exploring Milwaukee, look forward to kicking back in the cozy living room, or on the patio. This duplex has 2 bedrooms; a King bed master, and one bedroom with two Twins. There is one charming bathroom with a bathtub. Well stocked kitchen, and plenty of backyard space. The lower tenant is respectful of guests.

4.93 out of 5 average rating, 161 reviews
Top Guest favourite
Home in Cudahy

Lake Michigan Views • Private Cedar Sauna

Private cedar barrel sauna, cozy fireplace, and peaceful outdoor spaces just steps from Lake Michigan. Unwind beneath the string lights in the seasonal Garden Lounge, gather around the chiminea, or stroll scenic bluff trails along the lake. Just minutes from downtown Milwaukee, beaches, breweries, restaurants, museums, festivals, and sporting events, this thoughtfully designed getaway is the perfect home base to relax, recharge, and explore year-round

5.0 out of 5 average rating, 60 reviews
Top Guest favourite
A spacious bedroom features a white bed adorned with decorative pillows and a textured throw blanket. A striking lion portrait hangs above the bed. Natural light fills the room through a nearby window, with soft curtains partially drawn, complementing the warm brown walls.
Home in Milwaukee

Mid-Century Inspired Upper Duplex in Bay View

Step through the carpeted private entrance of this 2nd floor home, and into a mid-century interior with a modern twist. Eye-catching touches include the collection of retro radios that give it its name, stylish decor and a subway-tiled bathroom. This cozy apartment is decorated in a mid-century theme with a modern twist. It's on the second floor of a duplex. You will have your own carpeted entrance located in the back of the property.

4.95 out of 5 average rating, 257 reviews
Guest favourite
A sturdy entrance door with multiple glass panels is framed by textured stone walls. The door features a decorative wreath adorned with sunflowers and autumn accents, creating a welcoming entry point.
Apartment in Shorewood

English Tudor -Floor 3 Suite blocks from the beach

Total 4 beds - 2 Queen, 1 twin, 1 full Floor 3 is a private, peaceful, comfortable suite. Newly tiled bathroom and renovations throughout. Comfortably Sleeps 6 beds (2 queen, 1 double, 1 twin. There is 1 full bathroom. I have a cat that goes in the lower level stairway to access their restroom in the basement. But they do not go in the 3-floor unit. I also have 2 lovely dogs you may see when coming in.

4.85 out of 5 average rating, 129 reviews
Guest favourite
The exterior of a historical mansion is displayed, featuring intricate architectural details and multiple levels. Large windows and black front doors offer an inviting entrance. A grassy area with small shrubs lines the front, providing a well-maintained appearance against a cloudy sky.
Apartment in Milwaukee

Historic Lower East Side Apartment with Lake Views

This is one unit in a historical mansion with lake views! Layout is shotgun, open concept with a SMALL functional kitchen. Definitely gives off a pied-à-terre vibe. You have direct access to the back patio and a dedicated parking space around the corner. This unit is in the heart of the lower east side- close to the art museum, cathedral square, Brady st, 3rd ward, as well as the best restaurants and bars in MKE .

4.91 out of 5 average rating, 781 reviews
Top Guest favourite
A welcoming living area features a dark leather sofa and loveseat, complemented by a wood coffee table atop a plush area rug. Natural light enters through two windows, enhancing the space's warmth. Artwork is displayed on the wall, adding a touch of character.
Apartment in West Allis

Clean 2 bedroom/1 bath close to everything!

Charming, recently and tastefully furnished 2 bedroom 1 bathroom apartment with private entrance and parking. Close to downtown, shopping malls, zoo, hospital, airport, and main freeways. Full kitchen with stove, microwave, coffee pot, toaster, and kitchenware. Unit has TVs and WiFi. Coin operated laundry is accessible in building. Why stay at a hotel when you can feel at home in this lovely unit?

4.96 out of 5 average rating, 232 reviews
Guest favourite
A well-appointed living area features a black leather sofa facing a rustic coffee table made of reclaimed wood. A large mirror and artwork adorn the walls, while a mounted animal head adds character. Plants are placed on the table and around the space, enhancing the room's ambiance.
Apartment in Bay View

Beautiful Bayview 2 Story Loft w/Skylights, Wetbar

Beautiful huge 2 story Bayview Loft with skylights - best location in Milwaukee right next to South Shore Park includes wet bar and two living spaces with huge master suite. Vintage antique styling meets modern amenities with Memory-Foam mattresses, toilets with heated seats and bidets, Reverse Osmosis drinking water system, Nespresso coffee maker, natural gas fireplace.

4.97 out of 5 average rating, 319 reviews
Guest favourite
The exterior of a charming stone home is presented, featuring a warm brown roof and a welcoming entrance. Green grass surrounds the front yard, complemented by neatly trimmed shrubs and small decorative trees. Nearby houses in a peaceful neighborhood can be seen in the background.
Home in Milwaukee

Spacious 2 br Complete Living

Enjoy a stylish experience at this centrally-located Milwaukee home that's minutes from downtown entertainment and sporting events. This spacious home is located in a very quiet and peaceful neighborhood that is mostly home ownership, with plenty of restaurants to choose from.

5.0 out of 5 average rating, 29 reviews

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