Milwaukee Holiday Rentals

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Holiday Rentals in Milwaukee

The Plaza Hotel

3.0 star property
8.6 out of 10, Excellent, (1054)
"We appreciated being able to bring our pup to the property for the night. We also appreciated how the parking lot was being maintained/salted during our stay! Thank you"
The price is AU$322
includes taxes & fees
27 Jan - 28 Jan
The Plaza Hotel

Kasa Westown Milwaukee

4.0 star property
9.0 out of 10, Wonderful, (67)
"Excellent location for our family. Will return!"
The price is AU$189
includes taxes & fees
23 Jan - 24 Jan
Kasa Westown Milwaukee

New Years!! Hot Tub, Fishing Pond, Events! Winter Discounts! Weddings, Pool

9.8 out of 10, Exceptional, (194)
"We stayed here for the weekend and it was wonderful! The kids loved the playset outside and the game room! Definitely would recommend to other groups and families. "
New Years!! Hot Tub, Fishing Pond, Events! Winter Discounts! Weddings, Pool

Amazing Five Bedroom Milwaukee Vacation Home!!

10.0 out of 10, Exceptional, (40)
"We have a family of 10 and this house was perfect for us. There was entertainment for all ages. Large areas for everyone to gather but also gave everyone their own space. Loved watching movies while swimming in the pool. Host was excellent to work with and process was easy. "
Amazing Five Bedroom Milwaukee Vacation Home!!

Charming Riverwest Retreat

9.4 out of 10, Exceptional, (16)
"Which the property had off street parking. The kitchen did not have pot-holders and tissues. Nice property."
Charming Riverwest Retreat

Step right up, step right up! Welcome to the grand, the unique, the unparalleled

9.8 out of 10, Exceptional, (67)
"The house was very roomy and lots of places to hang out with family and friends. It was awesome that it was close to the lake. The owner had forgotten we were coming and didn’t have the refrigerator cleaned out and our check-in process was a little awkward because we didn’t have the keypad information. "
Step right up, step right up! Welcome to the grand, the unique, the unparalleled

Modern and Luxurious Milwaukee Home Centrally Located Near Local Amenities!

9.8 out of 10, Exceptional, (18)
"Charming historical area with plenty of street parking. This unit was spacious, smartly renovated and clean. We would stay here again and recommend to others.again. "
The price is AU$878
includes taxes & fees
23 Jan - 24 Jan
Modern and Luxurious Milwaukee Home Centrally Located Near Local Amenities!

Sleeps up to 30 people comfortably, there's karaoke pool table and so much more.

8.0 out of 10, Very good, (9)
"We were unable to check in until several hours after the check in time due to a plumbing issue the host did not proactively communicate about. Host did not use the entry keypad code they requested we set. The listing indicated 7 bedrooms for a total of 2 king beds, 1 queen, 10+ twin beds, and additional futons. On arrival there was only 1 double bed, 10 twin beds, a couple of futons. We had to make alternate accommodations for half our group. The host did not respond to outreach at all the first...
The price is AU$1,348
includes taxes & fees
23 Jan - 24 Jan
Sleeps up to 30 people comfortably, there's karaoke pool table and so much more.

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

9.6 out of 10, Exceptional, (233)
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Frank Lloyd Wright-Designed House In Milwaukee, WI, 4 Bed 2.5 Bath, Sleep10

Nice three 3 bedroom unit with free parking and wi-fi

6.0 out of 10, (19)
"Could use updated, but was clean and comfortable."
The price is AU$322
includes taxes & fees
23 Jan - 24 Jan
Nice three 3 bedroom unit with free parking and wi-fi

15 minutes to anywhere in and around Milwaukee.

10.0 out of 10, Exceptional, (30)
"Was not expecting to be in the basement of a home that they created into a little apartment. The home owner showed us to the lockbox and explained everything on getting in and out. There were house rules like quiet hours after 10pm which would have been good to know, it was NYE and we wanted to play music after our concert but we were to scared to be loud or wake up the home owner. There was also only one bathroom connected to the bedroom so any friends sleeping on the couch in the living room...
The price is AU$266
includes taxes & fees
24 Jan - 25 Jan
15 minutes to anywhere in and around Milwaukee.

MKE Mansion - Both Wings

9.8 out of 10, Exceptional, (12)
"The house is exactly as listed. There were some small functional issues with the house that the landlord responded to immediately. All around great stay. "
The price is AU$2,392
includes taxes & fees
26 Jan - 27 Jan
MKE Mansion - Both Wings

Walker's Point House Near Downtown Milwaukee

9.8 out of 10, Exceptional, (31)
"We were all very pleased with the property and the owner was very helpful. "
Walker's Point House Near Downtown Milwaukee

Urban Oasis minutes to Fiserv, Summerfest & more

9.0 out of 10, Wonderful, (14)
"Great location, lovely, plant-filled space. Bummer that the shampoo and soap were empty in bathroom and there was nothing complimentary in kitchen beyond salt and pepper. Coffee filters, but no coffee or tea or anything. Very minimalist. Clean a d super comfortable."
Urban Oasis minutes to Fiserv, Summerfest & more

Safe location lively Wauwatosa and within 10 min of what Milwaukee has to offer.

9.2 out of 10, Wonderful, (23)
"As listed, clean and perfect communication. Located a short walk from the shops on 68th and Wells, and a short drive to Marquette and downtown Milwaukee. "
Safe location lively Wauwatosa and within 10 min of what Milwaukee has to offer.

Booth Upper · Amazing view, Modern Space

10.0 out of 10, Exceptional, (35)
"Loved everything about this place. Spacious, nice, well stocked, great view of the city. Really liked how it was close enough to the city to get there in 10 minutes, but far enough to have some quiet and privacy. Not sure if I’ll ever visit Milwaukee again but I will definitely look for this place again if I do."
Booth Upper · Amazing view, Modern Space

4 bedroom house walking distance from Milwaukee Bucks Fiserv Forum

9.8 out of 10, Exceptional, (22)
"Lots of bedrooms. A great space for gathering with our friends and family."
4 bedroom house walking distance from Milwaukee Bucks Fiserv Forum

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

9.4 out of 10, Exceptional, (56)
"Very nice house and location, clean and nice neighborhood. Only downfall I that I feel as if is the listing is inaccurate for 10 people to sleep there. It does not sleep 10 people comfortably. The couch is small (2 cushions) and supposed to count as a bed. It would be nice if it was a pull out couch with a bed. And, there are 3 top mattresses stuffed in a closet that are supposed to be used for beds. This may work for children to throw them on the floor to sleep, but for adults, an actual bed...
The price is AU$481
includes taxes & fees
23 Jan - 24 Jan
Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find

Schlitz Castle: Huge 5BR/4BA Sleeps 12 w/ Double Kitchens & Living Rooms

10.0 out of 10, Exceptional, (16)
"Overall, we votes as a family and this trip was one of our favorite stays! Kyle's communication from the start was on point! The Schlitz Castle is a two flat that gives everyone their own space- while also feeling like a very large single family. This home is also one of the most well appointed & generous on so many levels. My 17 yr old said this would be the house he’d stay at if there was a zombie apocalypse! No detail is left- the kitchen is fully stocked- including seasonings and the...
The price is AU$1,792
includes taxes & fees
25 Jan - 26 Jan
Schlitz Castle: Huge 5BR/4BA Sleeps 12 w/ Double Kitchens & Living Rooms

The Malt House

4.0 star property
9.0 out of 10, Wonderful, (2)
"Amazing property/location! Surrounding neighborhood and ambiance is very cool. Not a very upscale property/bedding/furniture. However, a fine tradeoff for price and ambience. The parking access during winter is also a nice touch"
The price is AU$258
includes taxes & fees
27 Jan - 28 Jan
The Malt House
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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Other types of properties in Milwaukee you may be interested in

Saint Kate - The Arts Hotel

4.0 star property
9.8 out of 10, Exceptional, (2138)
"Stayed at this hotel multiple times and I love it. Wonderful staff and easy check in. Right down by Fiserve and other spots to walk that are fun"
The price is AU$242
includes taxes & fees
11 Feb - 12 Feb
Saint Kate - The Arts Hotel

Hilton Milwaukee

4.0 star property
8.2 out of 10, Very good, (1059)
"Beautiful architecture "
The price is AU$174
includes taxes & fees
29 Jan - 30 Jan
Hilton Milwaukee

The Pfister Hotel

4.5 star property
9.4 out of 10, Exceptional, (1611)
"I loved this historic property , you walk in they give you champagne , we went to the lounge had some drinks and had dinner at the restaurant , after that we walked around and went to a couple bars - the hotel was beautiful , i would definitely stay there again!"
The price is AU$277
includes taxes & fees
11 Feb - 12 Feb
The Pfister Hotel
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.

Frequently asked questions

Are there holiday rentals in Milwaukee?

Yes, there are holiday rentals in Milwaukee close to Betty Brinn Children's Museum, or you can select a more secluded option if you're looking for a relaxing stay. Travellers who like culture and the arts give Milwaukee high marks for its great live music and acclaimed theatre scene. The lively festivals and fascinating museums are some other things you might like to check out during your trip.

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

Amazing Five Bedroom Milwaukee Vacation Home!!: This highly rated holiday home rental in Milwaukee offers an indoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a balcony and a garden. Some other top choices in Milwaukee are New Years!! Hot Tub, Fishing Pond, Events! Winter Discounts! Weddings, Pool and Modern and Luxurious Milwaukee Home Centrally Located Near Local Amenities! .

How many holiday rentals are there in Milwaukee?

Choose from 516 Expedia holiday rentals in Milwaukee for a memorable holiday.

What can I see and do in Milwaukee?

Cultural attractions include Marcus Center for the Performing Arts and Riverside Theater, whereas Veteran's Park and Mitchell Park Horticultural Conservatory are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Pabst Theater and Milwaukee Public Market.

What’s a holiday rental in Milwaukee like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Milwaukee. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a family trip or a small group gathering.