Holiday rentals in Milwaukee County

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Top-rated holiday rentals in Milwaukee County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost
A spacious living area is highlighted by large windows allowing natural light to fill the room. Comfortable seating is arranged around a wooden coffee table, with decorative pillows adorning the couch. The decor includes wall art and plants, contributing to a homey feel.
Home in Milwaukee
4.81 out of 5 average rating, 16 reviews

Gallery House

Welcome to our 1924 Brick Bungalow, The Gallery House! Located in the prestigious Murray Hill Neighborhood, we are a but a 10 min drive North of central downtown Milwaukee. Enjoy easy access to the best neighborhoods; such as Downer Woods, Riverwest, Shorewood, Walkers Point, Bayview, and the Third Ward. We are located 4 blocks from the Milwaukee River, and 1 short mile to the beaches & parks on Lake Michigan. There are grocers, cafe's, a Walgreens, and places to eat in the neighborhood

Guest favourite
A bright living area showcases a comfortable seating arrangement with decorative cushions. Potted plants add greenery, and light streams in through the large windows. Artwork adorns the walls, while a mix of textures is provided by the rugs and furnishings.
Flat in Milwaukee
4.94 out of 5 average rating, 428 reviews

Bay View MKE Hideaway - with Parking!

Cozy, inviting, one bedroom apartment in the heart of Bayview, literally steps away from some of Milwaukee's best restaurants, bars and shops! One of two Airbnb guest spaces in our house, this downstairs apartment is our home base when we're in Milwaukee, and we love sharing it with guests when we’re on the road! We are within five minutes of Summerfest grounds and East Side & Historic Third Ward districts, and within 10 minutes of the airport, downtown, Marquette University, and Miller Park.

Top guest favourite
The living room features a stylish tan sofa accompanied by a textured throw and decorative pillows. A round mirror hangs on the wall, reflecting the room's layout. A light fixture hangs overhead, and colorful artwork is displayed. A modern coffee table is positioned on a striped rug.
Home in Milwaukee
4.93 out of 5 average rating, 147 reviews

Funky 2BR in Prime Bay View - w/ Parking

Perfectly located on the main strip of KK in MKE's eclectic Bay View directly next to restaurants and bars. Minutes from downtown, Summerfest, art museum. You’ll have the entire first floor of this sunny duplex. Stylishly designed - 2 bedrooms with Casper mattresses, a bright kitchen with seating area, record player, a work space in the master, and a comfy living room with a smart TV. The space has a small backyard area, an in-unit washer & dryer as well as 1 off-street parking space.

Guest favourite
A dining area features a round table surrounded by black chairs with plush white cushions. Sunlight filters through large windows, highlighting the vintage sideboard and plant. An inviting living space is visible through an archway, showcasing a blend of decor and natural light.
Bungalow in West Milwaukee
4.97 out of 5 average rating, 202 reviews

Adorn Abode

Charming upper level hygge bungalow (2 unit home total). Ten minutes from anywhere. Tucked away in the quiet village of West Milwaukee. Full of natural light and curated vintage decor. Walking distance to a few restaurants and bars, as well as the American Family Field. Enjoy a cocktail on the front balcony and watch the sunset while indulging in a classic vinyl collection. Small balcony off of the kitchen to watch the sunrise and enjoy a cup of coffee. Perfect for adventuring or relaxing.

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.
Flat in Milwaukee
4.86 out of 5 average rating, 309 reviews

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.

Guest favourite
A cozy living area is presented with two dark leather sofas, accompanied by bright red cushions. A glass coffee table occupies the center, while light enters through two large windows adorned with navy blue curtains. A stylish lamp and a decorative piece complete the room.
Home in Milwaukee
4.9 out of 5 average rating, 336 reviews

Historic East Side Duplex, 3BD. No Cleaning Fee!

Minutes from downtown Milwaukee by car or bus, the whole group will enjoy easy access to the city from this central location less than a mile from the UWM campus. A block from the Urban Ecology Center and Oak Leaf Trail access and easy walking distance to North Avenue's restaurants, bars, and the Oriental Theater, there's no shortage of activities, entertainment, and dining options around this historic and charming East Side abode. Or stay in with our grill and fire pit.

Guest favourite
Home in Milwaukee
4.9 out of 5 average rating, 93 reviews

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!

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
4.92 out of 5 average rating, 155 reviews

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.

Superhost
Home in Milwaukee
5 out of 5 average rating, 4 reviews

Historic Walker’s Point Home • Sleeps 10 • Garage

Welcome to Rosa Luna, a beautifully restored late-1800s cottage in the heart of Walker’s Point. Enjoy vintage charm, original hardwood floors, 3 bedrooms, a spacious skylit attic retreat with 2 double beds, a private fenced backyard, and secure 2-car garage parking. Minutes from downtown, Bay View, restaurants, coffee, nightlife, Summerfest, and sporting events—it’s the perfect home base for your Milwaukee getaway for families or groups of friends.

Top guest favourite
A bright living area showcases a cozy blue sofa adorned with patterned cushion covers. A round area rug is centered on the hardwood floor, with a plush orange armchair positioned nearby. Floor-to-ceiling curtains frame the window, creating a warm ambiance.
Home in Milwaukee
4.94 out of 5 average rating, 170 reviews

Swan City Cozy Boho in Bay View

Welcome to Swan City located in the heart of Bay View. With beautiful hardwood floors and a cozy boho-inspired decor, our space is designed to make you feel right at home from the moment you arrive. Centrally located, we are within walking distance of several restaurants, bars, and co-ops. This community is known for its lively atmosphere and friendly locals, and there's always something exciting to see, or an event to attend in the neighborhood.

Top guest favourite
Home in Greenfield
4.97 out of 5 average rating, 35 reviews

Cozy, Cute, & Clean !

Cozy, Cute, and Clean! SHORT TERM fully furnished rental available in a quiet neighborhood of Greenfield! 20 minutes or less drive to: Downtown Milwaukee, Lake Michigan, Brady Street, Am-Fam Field, UW-Milwaukee, Marquette University; Advocate-Aurora, Ascension, & Froedtert Hospitals, stores, restaurants, and just 40 mins from the IL border! Utilities included In-Unit Washer/Dryer **Perfect for Travel Nurses/Techs, and Business Professionals**

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.
Flat in Milwaukee
4.91 out of 5 average rating, 764 reviews

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 .

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