Holiday houses in South Milwaukee

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Top-rated holiday rentals in South Milwaukee

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
The interior features a vaulted wooden ceiling with decorative masks adorning the walls. A stone fireplace is prominently situated, providing warmth, while a dark stone countertop and wooden cabinetry define the kitchen area. A spiral staircase leads to additional spaces.
Home in Racine
4.91 out of 5 average rating, 266 reviews

“Rustic Farmhouse Retreat” at a working farm

A charming little farmhouse filled with antiques & eclectic artwork from all over the world. It is situated in the middle of a working farm that raises a plethora of exotic fruits, vegetables, shiitake mushrooms, and flowers for local gourmet restaurants. The house interior has a unique design decorated with beautiful hand crafted stonework accented with exotic driftwood trim from old wooden shipwrecks. Try our outdoor Neapolitan wood fired oven for the best pizza ever. A truly unique getaway!

Top Guest favourite
Townhouse in Bay View
4.88 out of 5 average rating, 109 reviews

*CLEAN* Craftsman Lakeside 3 Bedrm Bay View Duplex

**Sparkling Clean** newly renovated historic 100 year old UPPER duplex in the highly desirable South Shore Park neighborhood of Bay View. Resembles northern Wisconsin cabin with all of the creature comforts of being close to the city of Milwaukee. Just a block off the lake/park/beach/restaurants. Super spacious living room & full size dining room with 3 separate bedrooms and a bathroom with two vanities gives all of your guests ample room to be comfortable. Pull out beds avail Sorry, no pets

Guest favourite
The living area features a mix of seating options with a sectional sofa and a cozy lounge chair. Natural light enters through two windows, framed by curtains, and potted plants bring a touch of greenery. Artwork is displayed on the walls, enhancing the welcoming ambiance.
Apartment in Bay View
4.94 out of 5 average rating, 423 reviews

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.

Guest favourite
Home in Oak Creek
4.86 out of 5 average rating, 108 reviews

Spacious Ranch Home Oak Creek close to Airport

Chalet style ranch home is fully furnished and offers 2400 square feet of private usable space. The 3 bedrooms, living room, dining room, family room, 1 1/2 bathrooms, kitchen, and kitchen table area are all located on one floor. You will love waking up in the morning in this quiet suburban neighborhood and looking out the many windows at the park across the street. Close to the heart of Oak Creek Drexel Town Square, 4.6 miles from the airport, & 15 minutes from Downtown Milwaukee.

Top Guest favourite
A comfortable sectional sofa adorned with colorful throw pillows is positioned around a low wooden coffee table. A projector is set up for viewing, with a light-colored rug adding warmth to the space. Artwork in vibrant hues is displayed on the walls.
Home in Milwaukee
4.93 out of 5 average rating, 156 reviews

Quiet Bay View Getaway

Enjoy this modern, updated 1 bedroom, 1 full bath, private lower suite located across from the airport and just minutes from Lake Michigan, downtown, and trendy Bayview nightlife! Conveniently located less than 2 minutes from multiple freeways! Walking distance to many restaurants and coffee shops. Less than a 9 minute drive to Miller Park, Fiserv Forum, State Fair, and more! Perfect for couples or traveling professionals who want easy access to everything Milwaukee has to offer!

Superhost
Home in Bay View
4.93 out of 5 average rating, 143 reviews

Bright 1.5BR in the Heart of Bay View - w/ Parking

Perfectly located in Milwaukee’s eclectic Bay View 4 blocks from the lake. Minutes from downtown, Summerfest, art museum, etc. You’ll have the entire second floor of this sunny duplex. The space is open concept - 1 bed with a King Casper mattresses, a bright kitchen with tons of space, a stylish living room with art throughout, and an office (with an air mattress). Fenced-in back yard that's great for pets and chill around the outdoor table for optimal hangs and BBQs.

Top Guest favourite
Guest suite in Sussex
4.99 out of 5 average rating, 153 reviews

Garden Retreat in law Suite

Welcome to our in-law suite apartment featuring a full eat-in kitchen, living room, queen bed in large bedroom, walk in closet and full bathroom with walk-in shower. Our beautiful two acre yard has many areas to relax in, including a hammock and fire pit for the evenings. Twenty mins. to Erin Hills and Holy Hill and a half hour to most downtown Milwaukee attractions, as well as the RNC activities taking place this summer. Lots of city tips and suggestions for our guests.

Top Guest favourite
Guest suite in South Milwaukee
4.99 out of 5 average rating, 74 reviews

Historic Hawthorne House

Nestled just steps from Grant Park Beach & Lake Michigan, the scenic Seven Bridges Trail, and the lush Grant Park Golf Course, this unique rental offers a blend of history, charm and comfort. Only a 10 minute drive to Mitchell International Airport and an easy 20 min drive to downtown Milwaukee. Whether you're here to unwind in nature, explore the local parks, enjoy a peaceful lakeside stay, or enjoy the best that Milwaukee has to offer this home has everything you need.

Superhost
A modern living area features exposed brick walls and a comfortable gray sofa, complemented by decorative pillows. A geometric blue and white area rug is placed beneath a set of small, stacked tables. Natural light is provided by a nearby window, framed by greenery.
Apartment in Milwaukee
4.81 out of 5 average rating, 289 reviews

Heart of Walkers Point | 3BR | Spa Shower | AC

Enjoy a newly remodeled apartment nestled between Bayview and downtown Milwaukee. This 1,200 square foot space is ideal for group stays. Perfect for hosting a trip with friends to see your favorite band at Summerfest or to cheer on your favorite team at Fiserv Forum. Located in a very active neighborhood, above a festive bar, local tattoo shop, and nightlife within a very short walk of the bustling restaurants and local bars which can at times be heard.

Top Guest favourite
Home in Milwaukee
4.95 out of 5 average rating, 242 reviews

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.

Superhost
Home in West Allis
4.94 out of 5 average rating, 269 reviews

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!!!

Top Guest favourite
An aerial view captures the vibrant shoreline of Milwaukee, showcasing the expansive blue waters of Lake Michigan alongside lush green parks. The cityscape includes an array of buildings, with streets bordered by trees and well-maintained landscapes, creating a balanced urban and natural environment.
Apartment in Milwaukee
4.99 out of 5 average rating, 220 reviews

Lakeview Downtown Milwaukee Condo

This charming one bedroom offers a full kitchen, king bed, private full bathroom, dining and living room area. Conveniently located in Milwaukee's East Side - close proximity to lake paths and trails, Juneau park, Brady Street, Fiserv Forum, the Art Museum and Summerfest grounds! Stay here and start your day with a beautiful sunrise in one of the best locations Milwaukee has to offer.

Popular amenities for South Milwaukee holiday rentals