Holiday houses in South Milwaukee

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Top-rated holiday rentals in South Milwaukee

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Guest favourite

Home in Bay View

4.94 out of 5 average rating, 97 reviews

2BR Sunny Upper in Prime Bay View - w/ Parking

Perfectly located on the main strip of KK in Milwaukee’s eclectic Bay View directly next to bars, restaurants, and shopping. Minutes from downtown, Summerfest, art museum. You’ll have the entire 2nd floor of this sunny duplex. Stylishly designed - 2 bedrooms with Casper mattresses, a bright kitchen with seating area, a work space in the master, and a comfy living room with a smart TV. The space has 2 patio spaces, a small backyard area, an in-unit washer & dryer as well as 1 free parking space.

Guest favourite

Home in South Milwaukee

5 out of 5 average rating, 15 reviews

Small Mid-century Ranch

My cozy home is on a peaceful dead-end street with a park at the end, offering both tranquility and convenience. Located along the Oak Leaf Trail, it’s a perfect location for a ride or bike in minutes to Grant Park or Bender Park beaches. You can easily walk to local bars, restaurants, and public transportation, providing quick access to shopping and downtown Milwaukee. Whether you're seeking a relaxing backyard retreat or outdoor adventures, this location truly offers the best of both worlds.

Guest favourite

Apartment in Cudahy

4.93 out of 5 average rating, 75 reviews

Spacious place by lake Michigan

Spacious and updated 3-1 apartment a block away from lake Michigan, 5 minutes from Milwaukee Mitchell Airport and 1h15min away from Chicago O'Hare Airport. The kitchen has been recently remodeled and is fully equipped. All the water supply is 3-step filtered and therefore safe to drink and use for cooking. The place also has a dedicated office space which includes a large L-shaped desk. Onsite laundry and free onsite parking in a dedicated garage space are available to accommodate long stays.

Guest favourite

Apartment in Bay View

4.95 out of 5 average rating, 327 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

Condo in Milwaukee

4.83 out of 5 average rating, 116 reviews

Full Condo&Garage in Trendy Bay View Milwaukee

This practical and cozy condominium is located in the heart of Bay View right on historic KK Avenue. It is next to the quaint Morgan Park and a bus stop, across the street from Sprocket Cafe, minutes from the lake and walking distance from the greatest trendy shops, bars, restaurants, and other Bay View classics. Whether you are totally new to the Milwaukee scene or just visiting "home", we are glad to welcome you to this charming condo, perfectly placed to meet all your traveling needs.

Guest favourite

Apartment in Bay View

4.85 out of 5 average rating, 259 reviews

Lakeside Beauty

Stunning lower duplex on Lake Michigan in beautiful Bay View WI. Exceptionally large 2 bedroom unit boasts back yard overlooking Lake Michigan with fire pit for cozy evening fires. Unit is a mix of new and classic vintage. Walking distance to South Shore Yacht Club, South Shore Terrace Beer Garden, Award Winning restaurants, a unique European grocery store, and the second largest Farmer's Market in the state. Seven minutes to downtown Milwaukee. Owner lives upstairs. Two bikes available.

Top Guest favourite

Townhouse in Bay View

4.95 out of 5 average rating, 415 reviews

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!

Guest favourite

Home in Milwaukee

4.92 out of 5 average rating, 151 reviews

Quiet Bay View Bungalow, Extended Family Stay

Need a quiet getaway? This sunny and peaceful upper of a Bay View bungalow provides you with a relaxing atmosphere! A corner property built in 1924, this diverse neighborhood offers perfect opportunities for a stroll through tree-lined streets and rolling hills. Bike or walk the quiet neighborhood or find a peaceful park just blocks away. We want you to feel at home during your getaway and hope it is as special to you as it is to our family.

Top Guest favourite

Home in Milwaukee

4.94 out of 5 average rating, 204 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.

Top Guest favourite

Dome in Caledonia

5 out of 5 average rating, 41 reviews

Indigo Zen Garden

Whether you’re escaping for a romantic weekend, a unique family getaway, or a peaceful solo retreat, Indigo Zen Garden offers an enchanting blend of comfort and wonder. Choose from our clear geodesic Stargazing Dome, the romantic Moon Chaser bell tent, or the whimsical Dream Catcher children’s play tent—each thoughtfully designed for a cozy, rejuvenating stay.

Top Guest favourite

Apartment in South Milwaukee

5 out of 5 average rating, 51 reviews

Cozy private getaway, Hot Tub, Music theme

Enjoy the cozy fire while relaxing in the hot tub in the private coved patio. Artistic "gallery like" lower apartment is nestled in a beautiful wooded neighborhood just 15 mins from Milwaukee's Downtown. Near by scenic views of the MKE skyline, Hoan Bridge, Summerfest Grounds and steps away from Lake Michigan, golf course and Seven Bridges hiking attraction.

Superhost

Apartment in Bay View

4.85 out of 5 average rating, 241 reviews

Cozy Basement Space In Bay View by Lake Michigan

Our cool, relaxing, newly finished basement apt is located in charming Bay View in Milwaukee. Shared entrance to stair case, but WITH IT'S PRIVATE ENTRANCE this space was designed to give you a great place to stay while you visit Milwaukee. Only minutes away from lake and downtown. ✊🏻✊🏼✊🏽✊🏾✊🏿 BIPOC, LGBTQ+ 🏳️‍🌈 friendly. All are welcome

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Other great holiday rentals in South Milwaukee

Home in Oak Creek

5 out of 5 average rating, 6 reviews

Beautiful Oak Creek house

MeganRating, 5 stars1 month ago

We loved our stay at Aga’s! We would go back in a heartbeat. The kitchen is the bees knees!

Top Guest favourite

Private room in Racine

4.98 out of 5 average rating, 133 reviews

Cozy In Caledonia

AlekseyRating, 5 stars2 weeks ago

Great place to stay, because everything you would want

Guesthouse in Franklin

4.83 out of 5 average rating, 6 reviews

The Crows Nest Cottage 1

DeepaRating, 5 stars4 days ago

We booked this last minute since we needed a place for a week or so. This seemed to be the best around that matched our dates. I had to choose between the small cabin for the 3 of us and a bigger place in Milwaukee without much green space or guaranteed parking or even unsure about safety. I am glad we chose this one. Adam has designed the place very tastefully. The big scenic backyard makes it completely worth staying just for that. I loved watching the sunrise from the treehouse in the morning and sitting outside to get my work done. It gave us enough space to spread out and do our things. The kitchen was well stocked with utensils and coffee pods. There were enough linens and sheets. It was very easy to move the coffee table to use the daybed. I wish we had the time to check out his boat rental. Adam is very responsive and friendly. He was very accommodating since reached very late. We enjoyed having his presence and his house nearby even though we are not usually social.

Top Guest favourite

Private room in South Milwaukee

4.94 out of 5 average rating, 345 reviews

Awesome Milwaukee location!

JimRating, 5 starstoday

Mark is a gracious, friendly, and communicative host. The house is very clean. It even smells clean and fresh. Nice looking house and yard. Walkable to the lakeshore. Easily accessible to major roadways and public transportation. Would absolutely stay there again.

Home in Bay View

4.75 out of 5 average rating, 103 reviews

Steps From Lake | AC | Bayview Gem | 1BR

JasonRating, 5 stars1 week ago

Good stay all around. Would stay here again if i visit Milwaukee.

Top Guest favourite

Private room in Saint Francis

4.96 out of 5 average rating, 283 reviews

Ginkgo House has a Room for YOU!

Marc-AndréRating, 5 stars4 days ago

Great place for our two-night stay in Milwaukee. Very nice room in a house, accessibility to living room and outside terrasse. Superb breakfast byMary Jo and Robert. They are very nice hosts. Close to downtown Milwaukee, but recluse enough for quietness. Also close to lake and many parks. We highly recommend !

Guest favourite

Townhouse in Saint Francis

4.88 out of 5 average rating, 41 reviews

Stylish home | Garage | Walk to Lake| Bay View

MichaelleRating, 5 stars3 weeks ago

I absolutely loved my stay in St. Francis, Wisconsin. The space was beautiful, cozy, and perfect for my short visit. It had everything I needed and felt like a peaceful retreat. Melissa was responsive and thoughtful, and the location was convenient yet quiet. I would definitely stay here again!

Superhost