A trip to Milwaukee should center around the standard beer, brats and cheese curds. But it should also include a bit of class. Brew City is the Midwest’s classiest metropolis, and if you don’t believe me, book yourself into one of these properties. These are the best luxurious Milwaukee Airbnbs for groups, family getaways, bachelor and bachelorette parties, and work retreats.
We hope you love the spaces and stays we recommend! Just so you know, Matador may collect a small commission from the links on this page if you decide to book a stay. Listed prices are accurate as of the time of publication.
Host your group at The Brewer’s Hill Inn and Gallery
Photo: Airbnb
There’s no better spot for a large group to experience Milwaukee’s beer culture than at the Brewer’s Hill Inn and Gallery. The kitchen and living spaces are designed for a reunion or bachelor party in Milwaukee, complete with foosball and arcade games. Taking a brew tour from the house is a cinch whether you organize it yourself or embark on a guided experience. But with so much on offer at the homestead, your crew will have just as much fun cracking open a case of PBR and lounging at the pad.
Sixteen guests, six bedrooms
Price: $764 per night
Beauty on Brady — luxurious large home in heart of city
Photo: Airbnb
This high-end home on Brady epitomizes luxurious, Wisconsin style. There’s plenty of space to lounge and the bedrooms are each done up with high thread-count sheets, spacious beds, and views out over the surrounding neighborhood. But the real star here is the backyard and deck. It’s built for group hangs, with ample seating and bistro lighting to set the mood. Play drinking games and let the conversation flow before heading out to experience Milwaukee’s nightlife and dining scenes, each within a quick Uber ride from the house.
Six guests, three bedrooms
Price: $1,900 per night
Grace Manor in Mequon
Photo: Airbnb
Simply put, this luxurious home in Mequon is the best Airbnb for a family vacation or bachelorette party in Milwaukee. It’s located on a secluded wooded lot and manages to capture the serenity of rural Wisconsin while being just minutes from downtown Milwaukee, should you wish to go out to explore. And if you visit in winter, its white facade blends so well with the surrounding snow that the outdoor lighting gives the home a calming air. Reserve this house for a holiday getaway and your kids will remember it so fondly that the trip will quickly become the stuff of family vacation legend.
Twelve guests, six bedrooms
Price: $990 per night
Luxurious East Side escape in Milwaukee proper
Photo: Airbnb
This East Side abode puts you within walking distance of Milwaukee’s trendiest bar and restaurant district. Downtown, sporting events, and brewery tours are also nearby so there’s no need to have a car for your stay — though the home has a garage should you be driving in. The backyard is fenced in and it’s a nice place to hang out for and pregame, with a grill and lounge seating. Inside, your crew can spread out upstairs and in the basement. It’s well-appointed and clean, with all the trimmings of home for a luxurious stay in Brew City.
Eight guests, three bedrooms
Price: $595 per night
High-end home located on a bluff above Lake Michigan
Photo: Airbnb
This is the house for when your crew is looking to go all out. Just outside Shorewood, looking over the tranquil waters of Lake Michigan, The Bluff House is a stunning rental. From the house, you can walk to Bradford and Atwater Beaches as well as Lake Park. But the home itself is quite a treat — with a master fireplace, quartz countertops, and a basement game room ready for bachelor or bachelorette parties as well as family gatherings. There’s also an outdoor entertaining area for summer and fall gatherings out by the water.
Fourteen guests, five bedrooms
Price: $3,300 per night
Restored classic home in heart of the city’s East Side
Photo: Airbnb
In Downer Woods just west of the coast, this north luxurious Mikwaukee Airbnb is walking distance to Atwater Beach and Lake Park, at a much more affordable rate than the above listing. It’s also close to the Calatrava-Milwaukee Art Museum and UVM, with easy access to bike paths as well as beer gardens. There’s a nice backyard and large detached garage, with a well-done living room. This is the spot for small groups or two couples looking to get away and experience Milwaukee with style.
Four guests, two bedrooms
Price: $231 per night
HGTV renovated home with large backyard
Photo: Airbnb
Experience the life of HGTV hosts in this luxurious Milwaukee Airbnb home within walking distance of the nightlife, dining, and brew pubs of Arbor View and Walker Square. The classic home is done to the standards of pro architects and interior designers, complete with a clawfoot tub and spacious bedrooms with comfortable, large beds. The backyard is a central gathering space complete with eight-person dining table, grilling area, bistro lighting, and plenty of space to hang out. An excellent option for families, groups, and work retreats.
Eight guests, three bedrooms
Price: $543 per night
Interior designer’s private loft with large patio
Photo: Airbnb
This high-end loft was put together by an interior designer and it shows — the decor, the flora, the layout, everything is done perfectly and to a point that you’ve never felt so welcome anywhere outside your hometown. Walk to the Third Ward, as well as the cafes and bars of Walker Point and the rest of central MKE. There’s also a large patio on which to plot your adventures across the city, making this a great stay for a small crew or a pair of couples.
Five guests, two bedrooms
Price: $273 per night
Bayview Beaux bright and artsy home in central location
Photo: Airbnb
Milwaukee has the style and pizazz of San Francisco, Miami, and New York. This Bayview home is proof — bright and airy, comfortable, and endlessly luxurious, you’re likely to spend as much time here as you will walking over to explore the 3rd Ward, Festival Park, and the rest of Brew City’s heart. The interior thrives off natural light, with views of the bay and the ferry over to Muskegon. If this is your first time in the city or you’re here for the purpose of exploring with someone for whom it is, there’s no better Milwaukee Airbnb to raise a toast to your good taste.
Six guests, two bedrooms
Price: $256 per night
Stylish loft with roof deck near city’s best restaurants
Photo: Airbnb
The best Milwaukee Airbnbs, like those everywhere, represent the style of their owner. They also tend to come with an acoustic guitar — coincidence? We think not. This trendy loft offers the guitar and a rooftop deck on which to jam, just across the river from the historic Third Ward and with views stretching from Menominee Valley to the west all the way out to the bay. The apartment is clean, functional, and comfortable, and offers easy access to beer, trendy dining, and cheese curds.
Six guests, two bedrooms
Price: $233 per night
Music lover’s loft with epic rooftop patio
Photo: Airbnb
If live music or nightlife is part of your Milwaukee plans, this luxurious loft with rooftop patio is the place to be. The unit is bright and well-heeled, and the rooftop patio puts it over the top. And it’s all right in the heart of Walker’s Point, Milwaukee’s coolest neighborhood. You’ll pregame with the best view in town before heading out from the unit to Restaurant Row, breweries, clubs, and more. 
Six guests, two bedrooms
Price: $235 per night