Holiday rentals with outdoor seating in Milwaukee County

Historic Home Sleeps 16 in MKEs Best Neighborhood

MAX of 16 guests! This luxury home has been designed especially for groups to gather and connect in-person. The huge second floor has ample space to gather everyone around a chef's kitchen and walk-out patio, while floors 1 & 3 are for sleeping Walk or bike everywhere! Minutes to Downtown, Third Ward, Bay View, Summerfest, and the best restaurants, breweries, trails, and music/sports venues. Just 5 blocks from easy freeway access and 12 minutes from airport! 2 driveway parking spots included

70s City Glamping RV By Lake, Unique Boho Retreat

My 70s GMC Motorhome "Painted Desert" has been renovated to offer my guests a glimpse into the past with a clean, warm, updated bohemian feel with all the amenities of home. There is an ample amount of windows for fresh air, light, and that cozy cabin feel. It is filled games, books, and art! Also a private yard featuring a picnic table, grill, & chiminea fireplace with tons of fresh chopped wood & kindle for you! There is nothing like this in Mke, a truly unique stay as central as it gets!

Large Condo w/Patio/ Old World 3rd next toFiserv

Our 1876 historic building is fully renovated! Located on the first floor is soon to be Sweet Connies bakery and breakfast location opening in 2024! Less than 1 block to the new Fiserv Forum. Enjoy the amazing patio. Lots of fun restaurants & bars on our street that run free shuttles to Brewers games. 1/2 block from the Riverwalk. Anticipate an electric, energetic night life. 1 parking spot behind the building can be rented if available for you stay. We do have a private garage a block away.

Gorgeous Bayview 2Story Loft w/Upper Deck/Firebowl

Located right on South Shore Park with views of Lake Michigan. Just a 3 minute walk to South Shore Beach and the Oak Leaf Trail, and just a 6 minute drive to downtown Milwaukee. This two story treetop loft occupies the upper two levels of a large historic house and has a large 400 sqft 2nd story deck overlooking the park and lake with a 4' natural gas fire bowl. Also features indoor bioethanol fireplace and full bar with a wine-chiller. The perfect place to kick back and relax with friends!

Private East Side Milwaukee flat with fenced yard

Enjoy the best that the East Side and downtown have to offer in this second floor standalone home on the Oak Leaf Trail with no shared walls, private fenced-in yard with spacious deck and patio, and private parking lot. This historic cream city brick building was constructed in 1897 and completely renovated in 2017 with custom features throughout. Gas fireplace, 70" TV in living room with custom hi-fi built-in stereo system, tons of natural light. Double guest suites with amenities galore.

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.

Blair House 1890

Amazing location! Beautiful, newly renovated 2BR upper floor of a duplex built in 1890 is your cozy launch pad to explore Milwaukee. Only steps from the many breweries, restaurants and shops on historic Brady St, this house is tucked away on a safe and quiet street with easy street parking. Relax outside under the shaded pergola or enjoy city views from the front porch. The location, great natural light, comfy bedrooms, and stylish decor- sets this house apart!

Large Victorian in Perfect Location!

My place is less then a block from Brady street and a 15 minute walk to the lake. Walking distance to over 75 restaurants and bars, many stores, 3 grocery stores and 2 pharmacies. A cheap uber ride to all Milwaukee activities and popular locations. 10 minute walk to a local bar that has a shuttle to Brewers games and summer fest. A huge and interestingly laid out victorian house with lots of amenities. Great place to host large groups, pets always welcome!

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!