Vacation rentals in South Milwaukee

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Top-rated vacation rentals in South Milwaukee

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Guest favorite

A spacious living area features a cozy tufted sofa adorned with decorative pillows, complemented by a circular glass coffee table. A vibrant area rug with floral patterns enhances the warm wood floors. Colorful artwork decorates the walls, adding a playful touch to the room.

Home in Bay View

4.92 out of 5 average rating, 125 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.

Top guest favorite

Loft in Walker's Point

4.94 out of 5 average rating, 521 reviews

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.

Guest favorite

A spacious living room features a vintage-inspired green velvet sectional sofa paired with plush pillows. A glass coffee table rests on a soft area rug, with natural sunlight illuminating the room. Decorative plants and a round mirror add to the inviting atmosphere.

Apartment in Bay View

4.95 out of 5 average rating, 836 reviews

Beautiful Bay View MKE Flat - w/parking!

This is a bright, sunny apartment on the upper level of a sweet little 1870's "Polish Flat" in the heart of Bay View, one of the city's most desirable neighborhoods! We are just steps away from some of Milwaukee's best restaurants, bars, taprooms, boutiques and coffee shops. The space features an efficiency kitchenette, living room, beautiful bedroom and renovated bathroom with walk-in shower! Close to East Side, Walker’s Point, Historic Third Ward, Summerfest, Mitchell Park and the airport.

Guest favorite

A well-maintained brick condominium is featured, with a welcoming entrance comprised of steps leading to a front porch. A manicured lawn surrounds the home, adorned with leafy trees and shrubs. Soft sunlight filters through the foliage, creating a serene outdoor atmosphere.

Condo in Milwaukee

4.84 out of 5 average rating, 132 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.

Top guest favorite

A cozy living area features a soft sofa adorned with colorful cushions, complemented by an accent chair. A stylish glass coffee table sits atop a geometric-patterned rug. Natural light filters through two windows, enhancing the warm ambiance of the space.

Townhouse in Bay View

4.95 out of 5 average rating, 437 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!

Top guest favorite

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

4.91 out of 5 average rating, 116 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!

Top guest favorite

A spacious living area features a blue sectional sofa and an inviting armchair, complemented by an artistic Milwaukee-themed mural on the wall. Bright natural light enters through the windows, which are fitted with blackout blinds, enhancing the room's modern aesthetic.

Home in Bay View

4.99 out of 5 average rating, 138 reviews

Cozy Bayview Guest House - Walk to entertainment!

Our Guest House (900 sq ft) is perfect for families & groups seeking a modern space within walking distance to some of the best restaurants, bars, breweries & cafes in Milwaukee's popular Bayview neighborhood. Enjoy your stay in comfort with 2 bedrooms & 5 total beds (1 king, 4 twins). Our Guest House is located directly behind the Main House on the same lot (separate houses). Street parking is available right outside our house with plenty of spots typically available.

Top guest favorite

A vibrant yellow wreath adorns a red door, leading into a welcoming space. Inside, a dining area is visible, featuring a round table surrounded by wooden chairs. A circular mirror reflects the textured wall with blue floral patterns, creating a lively and inviting atmosphere.

Bungalow in Bay View

4.96 out of 5 average rating, 318 reviews

Our Cozy Bay View Bungalow Getaway

Our relaxing, clean, fully equipped Bay View bungalow delivers a perfect getaway. We are equipped with fiber wifi (1 gig), 4K 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.

Guest favorite

A cozy living area features high ceilings and large windows that allow natural light to fill the space. A sectional couch, adorned with a patterned throw, faces a wall-mounted television. Two accent chairs are positioned nearby, complemented by decorative artwork and indoor plants.

Apartment in Walker's Point

4.89 out of 5 average rating, 251 reviews

Charming 1BR Loft • Parking + Walkable Location

Welcome to your stylish Milwaukee retreat! This 1BR loft blends historic Cream City charm with modern comfort. Soaring 15-ft ceilings, exposed brick, and oversized windows create a bright, open space. Enjoy a spacious king bed, fully stocked kitchen, and free off-street parking — rare in this neighborhood. Walk to the Third Ward, Walker’s Point, and Milwaukee’s best restaurants, breweries, shops, and the vibrant riverfront. Perfect for both work and play.

A comfortable living area features a mix of patterned armchairs and a brown sofa. A wooden coffee table sits in the center, accompanied by a side table with a lamp. A wall-mounted TV is visible, along with large windows allowing natural light.

Home in Milwaukee

4.9 out of 5 average rating, 162 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.

Guest favorite

A spacious bedroom features a white bed adorned with decorative pillows and a textured throw blanket. A striking lion portrait hangs above the bed. Natural light fills the room through a nearby window, with soft curtains partially drawn, complementing the warm brown walls.

Home in Milwaukee

4.94 out of 5 average rating, 216 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 favorite

The bright living area features tall, arched windows allowing natural light to fill the space. A spacious sectional sofa is adorned with various textured throw pillows, while a colorful area rug anchors a wooden coffee table. Decorative plants and wall art enhance the airy atmosphere.

Apartment in Walker's Point

4.98 out of 5 average rating, 198 reviews

Cozy Vibes Apt | City View | Gym | Free Parking

Cream City historical brick building with incredible views of signature landmarks of Walkers Point. Cozily designed space by interior designer to make a romantic getaway or personal solo retreat to concentrate on your higher purpose. Very safe building and walking distance from foodie restaurants, breweries, jazz clubs, and the famed Iron Horse hotel. A perfect getaway for you and yours.