Holiday rentals with outdoor seating in Milwaukee

NEW 2Br Downtown Home w/ Garage, Yard, Walkable

Nestled in the vibrant Walker's Point neighborhood, this charming home offers the perfect urban retreat. The stylish 4-bedroom abode combines modern amenities with cozy ambiance; whether you're exploring the bustling streets or enjoying a night in, this home provides a quiet and convenient base for your Milwaukee adventures. With easy access to eclectic dining, unique shops, and lively entertainment, you'll find plenty to see and do. 5 Min to Historic Third Ward 10 Min to Milwaukee Art Museum

Clock Tower Loft Close to Key Attractions

This cozy quiet apt is softly illuminated by the full moon face of the Allen-Bradley Rockwell Clock Tower, a beacon in Milwaukee’s hip and historic Walker’s Point. Relax on the balcony and enjoy garden views plus treats & refreshments. Head out on a stroll or Bublr bike to discover great eats, crafted beers & spirits. Close to: HD Museum, Fiserv Forum, AmFam Field, theaters, museums & the lakefront. Welcome solo adventurers, couples & biz travelers! Easy access to Interstate, Airport & Amtrak.

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.

Belleview House: Hot Tub, Fire Table, Fenced Yard

Welcome to Belleview House, a delightful pet-friendly 3-bedroom home nestled in the heart of the vibrant Murray Hill/East Side neighborhood. We have renovated and redecorated the entire home and backyard (November 2025)! ✔ Hot Tub - closed during quiet hours ✔ Fast Wi-Fi ✔ Workspace ✔ Smart TVs ✔ Comfy king, queen, and twin beds ✔ Fenced Backyard with outdoor fire table ✔ Lawn bowling, horseshoe & cornhole ✔ Outdoor dining table ✔ 0.9 mi to Bradford Beach on Lake Michigan ✔ Stocked kitchen

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.

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.

Vintage Bay View - Big Backyard, Big 1 Bedroom

Welcome to your Milwaukee getaway! Located in the Bay View area, you're walking distance from the best farm-to-table restaurants, music venues, art fairs, and craft beer in the city. Not only that, but Lake Michigan's beaches, Miller Park, and downtown are a short drive away. The location is ideal. The place was created with a 70's midwestern feel, with wood-paneled furniture pieces and mod design. It also boasts a giant kitchen and backyard with grill. We can't wait for you to visit!

Brewers Hill cottage, newly renovated near FiServ!

Enjoy easy access to everything from this Brewers Hill cottage located between the upper Eastside and Downtown Milwaukee. When you’re here you’ll have walkability to many bars, breweries, eateries and Fiserv Forum. When your day concludes enjoy a small fire in the backyard with your favorite beverage. This house is perfect for small, younger families and it is also professionally cleaned and maintained after every guest! Ample parking in the private driveway and on the street

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.

Stylish Bay View Guest House, Walk to Bars+Dining

Our Guest House (700 sq ft) is perfect for families & groups seeking a modern space within walking distance to some of the best restaurants, bars, breweries & cafes in Milwaukee's popular Bayview neighborhood. Enjoy your stay in comfort with 2 bedrooms & 3 total beds (3 queens). Our Guest House is located directly behind the Main House on the same lot (separate houses). Street parking is available right outside our house with plenty of spots typically available.

Bright Eastside MKE cottage w/ FREE Parking

Welcome to our peaceful little cottage in the heart of Milwaukee. This adorable 2 bedroom, 1 bathroom home will meet all of your needs with 1 king bed, 1 queen bed, a fully stocked kitchen, wifi, driveway for off street parking, and bikes to use on the nearby Oak Leaf Trail. This is the perfect place to enjoy the friendly city of Milwaukee with a comfortable place to sleep at the end of the day. Enjoy all of the restaurants and shops on the Eastside of Milwaukee.

Near to all Milwaukee favorites/ Free Parking/WiFi

Make yourself, family or friends at home in this Cozy comfortable upper 2 bedroom, 1 bathroom house with Wisconsin charm! It’s a great location in the city of West Allis just a short drive to everywhere in Milwaukee. I appreciate that you considered my Airbnb listing! Please feel free to contact me on how I can improve your stay. Also, please take a moment to review my house rules. Can wait to host you, thanks!!!