Milwaukee Holiday Rentals

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Holiday Rentals in Milwaukee

The Plaza Hotel

3.0 star property
8.6 out of 10, Excellent, (1052)
"Great for kitchenettes and proximity to Milwaukee Museum of Art."
The price is AU$302
includes taxes & fees
25 Dec - 26 Dec
The Plaza Hotel

Kasa Westown Milwaukee

4.0 star property
9.0 out of 10, Wonderful, (66)
"Great place to stay! Just like a large apartment with all the amenities. Very conveniient. You can cook your own food and wash your clothes (has washer and dryer). Every item needed for you stay is provided. "
The price is AU$198
includes taxes & fees
24 Dec - 25 Dec
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)
"I went to detox, relax, and swim for a few days and did not bring family, but this is a terrific place for a family getaway with amazing pool, video games, plenty of beds, etc. Pleasant neighborhood as well. "
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!

10.0 out of 10, Exceptional, (15)
"The property was a good place to stay at! I will say it was what we needed for everyone to stay and have a place to sleep. The only issue with was trying to fit a vehicle in the garage. We took my friends Tahoe and it was a tough spot to fit in the garage, which we can tell it’s meant for smaller vehicles. And there were a pair of eyelashes set out on the coffee table. But overall for anyone with a bigger family or group of friends that need somewhere to stay I would recommend this location!"
The price is AU$880
includes taxes & fees
29 Dec - 30 Dec
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$1,359
includes taxes & fees
23 Dec - 24 Dec
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

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."
The price is AU$463
includes taxes & fees
26 Dec - 27 Dec
Urban Oasis minutes to Fiserv, Summerfest & more

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$2,374
includes taxes & fees
5 Jan - 6 Jan 2025
MKE Mansion - Both Wings

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

6.0 out of 10, (18)
"Could use updated, but was clean and comfortable."
The price is AU$326
includes taxes & fees
23 Dec - 24 Dec
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, (29)
"Each summer two of my adult children and I go on a baseball excursion to a baseball stadium we haven't been to before. This was walking distance from American Family Park. Our hosts were friendly and helpful and our stay was comfortable. We had easy access by car to restaurants and entertainment venues. It was a great place to stay., "
The price is AU$267
includes taxes & fees
2 Jan - 3 Jan 2025
15 minutes to anywhere in and around Milwaukee.

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

9.6 out of 10, Exceptional, (53)
"Home was large and well appointed. Great central location for all the Milwaukee activities we did. "
The price is AU$642
includes taxes & fees
6 Jan - 7 Jan 2025
Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find

Spacious Home Perfect for Families & Groups: Near Fiserv Forum & Brady Street!

10.0 out of 10, Exceptional, (4)
"Property was as described. Clean. Easy check in. Would stay there again."
Spacious Home Perfect for Families & Groups: Near Fiserv Forum & Brady Street!

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. "
The price is AU$592
includes taxes & fees
23 Dec - 24 Dec
Safe location lively Wauwatosa and within 10 min of what Milwaukee has to offer.

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

House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

9.8 out of 10, Exceptional, (17)
"Very warm and cozy. Great location close to everything."
The price is AU$423
includes taxes & fees
29 Dec - 30 Dec
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

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
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

The Pfister Hotel

4.5 star property
9.6 out of 10, Exceptional, (1573)
"This is an iconic hotel. It is a true step back in time experience. My wife and I have celebrated our last 3 wedding anniversaries, and we will continue this tradition."
The price is AU$279
includes taxes & fees
12 Jan - 13 Jan 2025
The Pfister Hotel

Saint Kate - The Arts Hotel

4.0 star property
9.8 out of 10, Exceptional, (2044)
"Staff was very friendly and professional. "
The price is AU$244
includes taxes & fees
11 Jan - 12 Jan 2025
Saint Kate - The Arts Hotel

Hyatt Regency Milwaukee

4.0 star property
8.4 out of 10, Very good, (1125)
"Great location for concert at Turner Hall and liked the King and I restaurant right across the street. Very comfortable bed. Secure entrance to own floor with room key. Buffet breakfast was good. Parking on site was convenient but a bit expensive."
The price is AU$179
includes taxes & fees
28 Dec - 29 Dec
Hyatt Regency Milwaukee
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 art 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 Modern and Luxurious Milwaukee Home Centrally Located Near Local Amenities! and New Years!! Hot Tub, Fishing Pond, Events! Winter Discounts! Weddings, Pool.

How many holiday rentals are there in Milwaukee?

Choose from 528 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 Milwaukee City Hall and Pabst Theater.

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.