Holiday rentals with outdoor seating in Milwaukee County

Bay View - Lake View on the Park w/Secret Lounge

Our 3 bedroom parkside condo in a beautiful historic renovated home is unique, peaceful, and near everything Bay View has to offer. Enjoy views of Lake Michigan from the front porch and dining room. Secret Vintage Lounge downstairs with antiques from all over the world is the perfect unique space - there is nothing else like this in Milwaukee! This 1st floor condo has perfect proximity to South Shore Park on Lake Michigan - Just a minute walk away from South Shore Beach and a lakefront trail.

Downtown Oasis: Hot Tub, Garage, 2 King Huge yard!

Bring the whole family to this great place with lots of room for fun. A rock throw away to Milwaukee central featuring the city's best restaurants, bars, shops, and attractions. This exclusive 1800sqft Ranch 3 bedrooms, 9 beds, 2 full and 1 half bathrooms to sleep up to 14 guests. It features everything your family & friends need: Large Kitchen, Wash/Dry, Outdoor Patio, large back yard and a 8 person Hot Tub! Walking to the Fiserv Forum and downtown. Attached Garage w/ Driveway. 1 Gig Internet

Close to Lake with Great Ammenities & Breakfast!

I want you to be able to do things here that you can't do in a hotel. If you're grillilng out, having a bonfire or watching movies all night long, you can turn up that volumn as loud as you want all night long! I posted my listing under "entire home" as you do get so much more than just renting "a room". When I have guests I stay in my office or bedroom so my guests feel more comfortable utalizing entire home & yard. In fact, if you don't ask for breakfast, you may not even see me at all.

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.

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.

MKE 2BR Flat+PKG|5M to Brewers |15M to Airport

Don't gamble on your stay—choose certainty with Painted Porch Stays, locally-owned haven committed to exceptional hospitality. This space accommodates up to 6 & offers a plethora of thoughtful amenities like snacks, dog treats, and a fully-stocked kitchen, stellar bathroom setup, and productive space w/ desks in each room. Minutes from MKE's top attractions and with parking, exploring is effortless. Experience our attention to detail and local charm for a truly memorable 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.

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.

Upgraded! 4BR in Milwaukee near Airport & Downtown

Bring the whole family to this upgraded home with lots of room for fun. Located directly across the street from Warnimont Golf Course & Lake Michigan, this home has plenty to do and see. The large, fenced in yard is perfect for your pets to run around. It's the perfect place to stay in Milwaukee! 12 mins to General Mitchell Airport, 14 mins to downtown, 16 mins to American Family Field and Fiserv Forum, 13 mins to Henry Maier Festival Park.

Historic Gem|Steps to UWM|Lake Mich|Free Parking

🔹 5-Star Rated | Superhost Quality | Fast Wi-Fi | Free Parking 🔹 🏡 Experience a Slice of Milwaukee’s History in a 100-Year-Old Home! Step inside this charming first-floor retreat—a beautifully preserved prairie-style home blending historic elegance with modern convenience. Located right across from UWM, this top-rated Airbnb is perfect for visiting students, faculty, families, and travelers looking for a relaxing, walkable neighborhood.

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.