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.

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

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, Backyard, Fire Table

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.

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

Our Cozy Bay View Bungalow Getaway

Our relaxing, clean, fully equipped Bay View bungalow delivers a perfect getaway. We are equipped with 1g wifi, 4K smart TV, dimmers, and a washer/dryer. Tastefully decorated, uncomplicated, and comfortable. There are cozy coffee shops, restaurants, and local bars just a few blocks from the house. The Bay View Dog Park is one block away. We have parking for two cars. We follow an Enhanced Cleaning Protocol, and are 100% smoke free without exception.

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.

Barclay House in Walker's Point

Our Walker's Point house is recently renovated, nearly everything is new. Relax in this stylish space which includes a private backyard, w/rear & front decks. Located next to cafes and some of Milwaukee's best restaurants. It is also within walking distance to the Summerfest grounds. We are minutes from Downtown Milwaukee, bike trails and the pedal taverns are just a block away from the house. We just recently added a new hot tub!

The Peacock Place w/ Shared Seasonal Outdoor Pool

This 3 bedroom, 1 bath, open concept lower unit of a duplex is located in Brewer's Hill. This unit has tons of natural light, original hard wood floors, pocket doors and claw foot soaking tub. This pet friendly unit has off street parking for 2 vehicles or motorcycles, and a private yard with patio and BBQ grill for your use. Walking distance to Brady Street, downtown and Fiserv Forum.