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South Milwaukee Holiday Rentals

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Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for South Milwaukee holiday rentals

Iron/ironing board, free WiFi, bed sheets
The Plaza Hotel

The Plaza Hotel

The Plaza Hotel
3.0 star property
Downtown Milwaukee
8.8 out of 10, Excellent, (1153)
"Loved this hotel! Clean friendly and cute!!"
United States
Sharon H
The price is HK$1,063
HK$1,254 total
includes taxes & fees
18 Jan - 19 Jan 2026
The Plaza Hotel
Fireplace
Kasa Westown Milwaukee

Kasa Westown Milwaukee

Kasa Westown Milwaukee
4.0 star property
Westown
9.0 out of 10, Wonderful, (120)
"Hosts get 5 stars for excellent communication. They checked in with me multiple times on my day of arrival to make sure everything was good and they gave very thorough instructions."
United States
Melissa
Kasa Westown Milwaukee
Hallway
ROVE LIVING/KL - Malt House

ROVE LIVING/KL - Malt House

ROVE LIVING/KL - Malt House
4.0 star property
Westown
9.0 out of 10, Wonderful, (11)
"The room was clean and spacious and very comfy the property was as well very beautiful and so much to look at … my family enjoyed the games that were in the room as well. We will definitely stay their again for our next visit "
United States
Ivan
ROVE LIVING/KL - Malt House
Terrace/patio
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
Kenosha
10.0 out of 10, Exceptional, (249)
"Great weekend, thank you for the space!"
United States
Ed C.
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
Outdoor pool, a heated pool
7 1/2 Acre Estate, Fish Pond, Events! Weddings, MSG Owner for discounts!!!

7 1/2 Acre Estate, Fish Pond, Events! Weddings, MSG Owner for discounts!!!

7 1/2 Acre Estate, Fish Pond, Events! Weddings, MSG Owner for discounts!!!
Caledonia
9.8 out of 10, Exceptional, (213)
"It was nice "
United States
Kevin C.
The price is HK$2,626
HK$5,044 total
includes taxes & fees
21 Dec - 22 Dec
7 1/2 Acre Estate, Fish Pond, Events! Weddings, MSG Owner for discounts!!!
Terrace/patio
17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18

17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18

17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18
New Berlin
7.8 out of 10, Good, (10)
"Awesome place!"
United States
Daniel M.
The price is HK$6,295
HK$14,155 total
includes taxes & fees
22 Dec - 23 Dec
17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18
Dining room
ROVE LIVING/KB - Prospect

ROVE LIVING/KB - Prospect

ROVE LIVING/KB - Prospect
3.0 star property
Lower East Side
7.6 out of 10, Good, (7)
"Our stay was great. The property was at it was described and expected. The owner was available via text and communicated with me when I had questions. We would stay again!"
United States
Vera
ROVE LIVING/KB - Prospect
Dining
Three bedrooms upstairs

Three bedrooms upstairs

Three bedrooms upstairs
Riverwest
9.6 out of 10, Exceptional, (78)
"He was very kind!"
United States
Hope
The price is HK$1,365
HK$1,821 total
includes taxes & fees
21 Dec - 22 Dec
Three bedrooms upstairs
Exterior
Downtown Eastside gem near Fiserv Forum Water St Brady St

Downtown Eastside gem near Fiserv Forum Water St Brady St

Downtown Eastside gem near Fiserv Forum Water St Brady St
Downtown Milwaukee
9.0 out of 10, Wonderful, (46)
"The check in instructions were perfect and not sure he could have laid that out any better. It's a nice place close to everything. We'd stay there again. "
United States
Chad-Tara A.
The price is HK$1,750
HK$2,568 total
includes taxes & fees
19 Dec - 20 Dec
Downtown Eastside gem near Fiserv Forum Water St Brady St
Property grounds
Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find

Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find

Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find
Lower East Side
9.6 out of 10, Exceptional, (67)
"It was clean and close to our wedding venue. "
United States
Kathy H.
The price is HK$1,537
HK$3,390 total
includes taxes & fees
19 Dec - 20 Dec
Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find
Smart TV, fireplace, books
Renovated Brady St. Classic

Renovated Brady St. Classic

Renovated Brady St. Classic
Downtown Milwaukee
8.4 out of 10, Very good, (10)
"Comfortable property in a great location. Liked that my adult children could walk to nearby restaurants, shops and bars. Neighborhood parking is limited, but not unusual for downtown-type stays."
United States
Mike F.
Renovated Brady St. Classic
Interior
NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms

NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms

NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms
2.0 star property
Lower East Side
9.8 out of 10, Exceptional, (20)
"Great property for our family group for a long weekend in Milwaukee. "
United States
Karl S.
The price is HK$1,136
HK$3,412 total
includes taxes & fees
11 Jan - 12 Jan 2026
NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms
Fridge, microwave, oven, stovetop
Stunning Upscale Retreat - Steps From Everything

Stunning Upscale Retreat - Steps From Everything

Stunning Upscale Retreat - Steps From Everything
Lower East Side
9.8 out of 10, Exceptional, (31)
"It was a great place and close to Brady street! Definitely recommend. "
United States
Hugh L.
The price is HK$1,575
HK$4,196 total
includes taxes & fees
25 Dec - 26 Dec
Stunning Upscale Retreat - Steps From Everything
Outdoor dining
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!
Johnson Woods
9.8 out of 10, Exceptional, (26)
"We stayed while attending the WI state fair. Quiet and safe neighborhood and really close to the fairgrounds. House was clean and easy to get to. We enjoyed our stay and the fenced in backyard was perfect for our Frenchie. "
United States
Roy W.
The price is HK$1,237
HK$2,577 total
includes taxes & fees
5 Jan - 6 Jan 2026
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!
Dining
Frank Lloyd Wright-Designed House In Milwaukee, WI, 4 Bed 2.5 Bath, Sleep10

Frank Lloyd Wright-Designed House In Milwaukee, WI, 4 Bed 2.5 Bath, Sleep10

Frank Lloyd Wright-Designed House In Milwaukee, WI, 4 Bed 2.5 Bath, Sleep10
Burnham Park
9.6 out of 10, Exceptional, (253)
"This spacious house is a true gem, lovingly preserved. Really enjoyed our stay!!!!"
United States
Lynne W.
Frank Lloyd Wright-Designed House In Milwaukee, WI, 4 Bed 2.5 Bath, Sleep10
Exterior
Wisconsin Treehouse Getaway!

Wisconsin Treehouse Getaway!

Wisconsin Treehouse Getaway!
Racine
9.6 out of 10, Exceptional, (26)
"We had a wonderful time staying here while visiting the surrounding area!"
United States
Collin C.
The price is HK$980
HK$1,907 total
includes taxes & fees
1 Jan - 2 Jan 2026
Wisconsin Treehouse Getaway!
Dining
Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers

Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers

Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers
Bay View
9.6 out of 10, Exceptional, (8)
"Great place!"
United States
Kathy R.
The price is HK$2,178
HK$4,036 total
includes taxes & fees
12 Jan - 13 Jan 2026
Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers
Interior
Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River

Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River

Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River
Waterford
9.8 out of 10, Exceptional, (367)
"Beautiful place, loved the fenced in yard for my Yorkies, very excited to stay there again!!"
United States
Pamela Q.
Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River
Dining
MKE Mansion - Both Wings

MKE Mansion - Both Wings

MKE Mansion - Both Wings
Downtown Milwaukee
9.6 out of 10, Exceptional, (23)
"Great house - big group I stayed with loved it and tons of places to sleep and hang out. Fantastic location by the water and near some good restaurants. Hosts were super responsive. "
United States
Henri E.
The price is HK$7,772
HK$12,740 total
includes taxes & fees
21 Dec - 22 Dec
MKE Mansion - Both Wings
Interior
Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub

Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub

Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub
Waukesha
9.8 out of 10, Exceptional, (19)
"Will come and stay again great host and home"
United States
Dion S.
The price is HK$1,050
HK$2,365 total
includes taxes & fees
21 Dec - 22 Dec
Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top South Milwaukee Hotel Reviews

The Brewhouse Inn & Suites

The Brewhouse Inn & Suites

10/10 Excellent
"Excellent experience. Employees super friendly and the rooms were exceptional "
Robert A 1-night trip
Posted 23 hours ago
The Brewhouse Inn & Suites

Find out more about South Milwaukee

Search for holiday rentals in South Milwaukee on Expedia! You can easily find your home rentals, villas, holiday apartments in South Milwaukee using one of the methods below:

  • View our selection of featured holiday rentals in South Milwaukee
  • Use the map to find apartments and other holiday homes in the South Milwaukee neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in South Milwaukee while they last

Look no further and take a look at our great range of rental properties in South Milwaukee!

Frequently asked questions

Are there holiday rentals in South Milwaukee?

Yes, there are holiday rentals close to the most popular sights in South Milwaukee, or you can select a more secluded option if you're looking for a relaxing stay. South Milwaukee is known for its riverfront and theatres.

What are some of the best holiday rentals that South Milwaukee has to offer?

The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft: This holiday home rental outside of South Milwaukee is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a pool table and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in South Milwaukee?

Choose from 3 Expedia holiday rentals in South Milwaukee for a memorable holiday.

What can I see and do in South Milwaukee?

Lake Michigan and Grant Park Beach are a couple of scenic spots to enjoy the outdoors, whereas South Milwaukee Performing Arts Center is one of the cultural attractions. In the wider area, you’ll find South Milwaukee Downtown Market and Milwaukee County Sport Complex.

What are holiday rentals like in South Milwaukee?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in South Milwaukee. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for families.