South Milwaukee Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for South Milwaukee holiday rentals

Smart TV, fireplace

Lake Michigan Waterfront Designer Villa

Lake Michigan Waterfront Designer Villa
Racine
9.8 out of 10, Exceptional, (16 reviews)
"The view of Lake Michigan was incredible. Had an amazing "
United States
Lauren O.
The price is HK$3,876
HK$5,559 total
includes taxes & fees
20 May - 21 May
Lake Michigan Waterfront Designer Villa
Dining

Victorian Hot Tub Oasis steps from Restaurants Pubs Coffee, Grocery & The Beach

Victorian Hot Tub Oasis steps from Restaurants Pubs Coffee, Grocery & The Beach
Shorewood
10.0 out of 10, Exceptional, (4 reviews)
"Great location. 1 block walk to a grocery store, a pharmacy, a great restaurant, AND a great coffee shop. Plenty of space for all."
United States
Nicki U.
The price is HK$3,601
HK$7,400 total
includes taxes & fees
11 May - 12 May
Victorian Hot Tub Oasis steps from Restaurants Pubs Coffee, Grocery & The Beach
Property grounds

Cozy 1-bedroom dome in lovely Caledonia with AC

Cozy 1-bedroom dome in lovely Caledonia with AC
Caledonia
The price is HK$1,480
HK$2,073 total
includes taxes & fees
10 May - 11 May
Cozy 1-bedroom dome in lovely Caledonia with AC
Living area

Serene 4-bedroom house with brook and forest in charming Racine

Serene 4-bedroom house with brook and forest in charming Racine
Racine
The price is HK$1,769
HK$3,820 total
includes taxes & fees
13 May - 14 May
Serene 4-bedroom house with brook and forest in charming Racine
Beach nearby

Charming home w/ fire pit, walk to Lake Michigan

Charming home w/ fire pit, walk to Lake Michigan
Shorewood
9.8 out of 10, Exceptional, (39 reviews)
"Host communication was excellent. House was clean and perfect for a little weekend getaway!"
United States
Grayson P.
The price is HK$1,018
HK$2,619 total
includes taxes & fees
11 May - 12 May
Charming home w/ fire pit, walk to Lake Michigan
TV

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

KK Upper · 2BR Sunny Upper in Prime Bay View - w/ Parking
Bay View
9.8 out of 10, Exceptional, (12 reviews)
"Super easy check in and out and great location. Would stay again!"
United States
Katie T.
The price is HK$1,221
HK$2,309 total
includes taxes & fees
20 May - 21 May
KK Upper · 2BR Sunny Upper in Prime Bay View - w/ Parking
Smart TV, books

Central location, newly remodeled, Backyard, Firepit, Hot Tub, A/C, Pet-Friendly

Central location, newly remodeled, Backyard, Firepit, Hot Tub, A/C, Pet-Friendly
Murray Hill
10.0 out of 10, Exceptional, (15 reviews)
"Beautiful house, excellent location, attentive host! It was a great stay! "
United States
Cary W.
The price is HK$1,521
HK$4,277 total
includes taxes & fees
10 May - 11 May
Central location, newly remodeled, Backyard, Firepit, Hot Tub, A/C, Pet-Friendly
Property grounds

Peaceful East Side-2 min UWM-Dining-Coffee-Parking

Peaceful East Side-2 min UWM-Dining-Coffee-Parking
Upper East Side
10.0 out of 10, Exceptional, (6 reviews)
"Great property and a great location. Lulu was an incredible and thoughtful host. "
United States
Lori B.
The price is HK$1,151
HK$2,246 total
includes taxes & fees
10 May - 11 May
Peaceful East Side-2 min UWM-Dining-Coffee-Parking
Smart TV, books

Sunny & Spacious 4BR East Side Stay ¦ Balcony ¦ Family-Friendly

Sunny & Spacious 4BR East Side Stay ¦ Balcony ¦ Family-Friendly
Upper East Side
9.4 out of 10, Exceptional, (8 reviews)
"Our son and his groomsmen stayed here for his wedding weekend. Great accommodations!"
United States
Kathy C.
The price is HK$1,309
HK$2,862 total
includes taxes & fees
13 May - 14 May
Sunny & Spacious 4BR East Side Stay ¦ Balcony ¦ Family-Friendly
Smart TV, books, music library, stereo

Charming Bungalow / ❤️ of Bay View / Parking - Central Air - Deck - Washer/Dryer

Charming Bungalow / ❤️ of Bay View / Parking - Central Air - Deck - Washer/Dryer
Bay View
10.0 out of 10, Exceptional, (29 reviews)
"This was our second time staying here and I can’t recommend it enough! The owners are so thoughtful and have left little treats or things for us each time we’ve stayed. They have everything you might need and then some, making it feel like home away from home. We will definitely stay here again. "
United States
Amber T.
The price is HK$1,409
HK$3,480 total
includes taxes & fees
13 May - 14 May
Charming Bungalow / ❤️ of Bay View / Parking - Central Air - Deck - Washer/Dryer
Interior

Irish Mist V @ Reefpoint Marina

Irish Mist V @ Reefpoint Marina
Racine
9.8 out of 10, Exceptional, (30 reviews)
"Nice spot to stay a night!"
United States
Joseph P.
The price is HK$1,174
HK$2,123 total
includes taxes & fees
27 May - 28 May
Irish Mist V @ Reefpoint Marina
Interior

Bayview Family-Friendly Stay

Bayview Family-Friendly Stay
Bay View
10.0 out of 10, Exceptional, (3 reviews)
"Best stay ever "
United States
Laniya mariee
The price is HK$1,585
HK$3,669 total
includes taxes & fees
20 May - 21 May
Bayview Family-Friendly Stay
Floor plan

Large Milwaukee Home 4BR Fast Wifi

Large Milwaukee Home 4BR Fast Wifi
3.0 star property
Fifth Ward
The price is HK$1,371
HK$5,564 total
includes taxes & fees
11 May - 12 May
Large Milwaukee Home 4BR Fast Wifi
TV

302/303- 2 condos joined for up to 12 people by Fiserv/3rd

302/303- 2 condos joined for up to 12 people by Fiserv/3rd
Westown
9.2 out of 10, Wonderful, (10 reviews)
"The location was great and the hosts were amazing!"
United States
Jill M.
The price is HK$2,341
HK$4,172 total
includes taxes & fees
22 May - 23 May
302/303- 2 condos joined for up to 12 people by Fiserv/3rd
Interior

Fun, style & comfort Eastside downtown 4 bedroom townhome near attractions

Fun, style & comfort Eastside downtown 4 bedroom townhome near attractions
Lower East Side
9.8 out of 10, Exceptional, (29 reviews)
"Tonga is a great host. House was perfect for our group of 10."
United States
Emily
The price is HK$1,127
HK$3,452 total
includes taxes & fees
11 May - 12 May
Fun, style & comfort Eastside downtown 4 bedroom townhome near attractions
Outdoor dining

3-bedroom vacation home just a short walk to Lake Michigan

3-bedroom vacation home just a short walk to Lake Michigan
Racine
9.2 out of 10, Wonderful, (35 reviews)
"Convenient location, comfortable house, thoughtful amenities, easy walk to lake, quick drive for food and various activities. "
United States
Beth S.
The price is HK$846
HK$1,857 total
includes taxes & fees
13 May - 14 May
3-bedroom vacation home just a short walk to Lake Michigan
TV

Large Victorian in Perfect Location!

Large Victorian in Perfect Location!
Downtown Milwaukee
10.0 out of 10, Exceptional, (32 reviews)
"The house was awesome and perfect for our stay. Tons of space, cool vibes, and you could tell the property was well cared for. The neighborhood was awesome and I highly recommend this location. We will look to book again in the future. "
United States
Donnie H.
The price is HK$3,488
HK$8,263 total
includes taxes & fees
11 May - 12 May
Large Victorian in Perfect Location!
Dining

MKE Mansion - Both Wings

MKE Mansion - Both Wings
Downtown Milwaukee
9.8 out of 10, Exceptional, (27 reviews)
"Host had everything laid out and clearly communicated well. "
United States
Dan S.
The price is HK$7,825
HK$12,891 total
includes taxes & fees
12 May - 13 May
MKE Mansion - Both Wings
Outdoor dining

Reef Point Marina - Vessel: "Freckled Fin" - East Dock 1, Slip 19

Reef Point Marina - Vessel: "Freckled Fin" - East Dock 1, Slip 19
Racine
9.4 out of 10, Exceptional, (15 reviews)
"A great adventure at the boat, a great hot tub, and a very clean pool, a wonderful location, very great view."
United States
Bogdan S.
The price is HK$1,057
HK$1,726 total
includes taxes & fees
22 May - 23 May
Reef Point Marina - Vessel: "Freckled Fin" - East Dock 1, Slip 19
Outdoor dining

Luxurious Craftsman Style Home in Famous Bay View with Hot Tub Oasis

Luxurious Craftsman Style Home in Famous Bay View with Hot Tub Oasis
Milwaukee
The price is HK$1,057
HK$4,211 total
includes taxes & fees
11 May - 12 May
Luxurious Craftsman Style Home in Famous Bay View with Hot Tub Oasis
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top South Milwaukee Hotel Reviews

Drury Plaza Hotel Milwaukee Downtown

Drury Plaza Hotel Milwaukee Downtown

10/10 Excellent
"Can't say enough about the staff at Dury. Maxwell and Kenneth were especially helpful. From opening doors to giving directions and suggesting places to see they were awesome. Very kind and easy to talk to they should be commended for their efforts. You don't want to lose employees like that and they both need to be rewarded. Thanks again for wonderful stay."
Tom 1-night trip
Posted 7 hours ago
Drury Plaza Hotel Milwaukee Downtown

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 in South Milwaukee close to South Milwaukee Performing Arts Center, 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?

Three bedrooms upstairs : This holiday home rental outside of South Milwaukee offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in South Milwaukee?

Choose from 4 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.