Waukesha Holiday Rentals

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Holiday Rentals in Waukesha

Holiday Home in Waukesha

9.8 out of 10, Exceptional, (16)
"Will come and stay again great host and home"
United States
Dion S.
The price is AU$465
includes taxes & fees
7 Dec - 8 Dec
Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub

Aparthotel in Downtown Milwaukee

3.0 star property
8.8 out of 10, Excellent, (1153)
"Loved this hotel! Clean friendly and cute!!"
United States
Sharon H
The price is AU$258
includes taxes & fees
4 Jan - 5 Jan 2026
The Plaza Hotel

Aparthotel in Westown

4.0 star property
9.0 out of 10, Wonderful, (117)
"Perfect location, so many things were within walking distance. Also felt very safe and more convenient than a hotel room. "
United States
Kaylee
The price is AU$256
includes taxes & fees
9 Dec - 10 Dec
Kasa Westown Milwaukee

Apartment in Westown

4.0 star property
8.8 out of 10, Excellent, (10)
"Loved the uniqueness, location and cleanliness of the unit."
United States
Teresa
The price is AU$247
includes taxes & fees
8 Dec - 9 Dec
ROVE LIVING/KL - Malt House

Holiday Home in New Berlin

8.4 out of 10, Very good, (8)
"We had an excellent family vacation at The Garden of Eden!!"
United States
Cheryl S.
The price is AU$3,454
includes taxes & fees
8 Dec - 9 Dec
17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18

Holiday Home in Caledonia

9.8 out of 10, Exceptional, (213)
"I want to move in. We had 13 guys for a bachelor retreat and this place was perfect. Plenty of room for us all and plenty to do. We expected to spend plenty of time exploring Milwaukee, but found ourselves hanging out at the pool or fishing in the pond when we weren’t relaxing in the game room. 10/10 would recommend!"
United States
Caleb B.
The price is AU$1,062
includes taxes & fees
21 Dec - 22 Dec
7 1/2 Acre Estate, Fish Pond, Events! Weddings, MSG Owner for discounts!!!

Holiday Home in Burlington

9.6 out of 10, Exceptional, (12)
"Very nice layout with lots of rooms and interesting places to be for a large group or family"
United States
Brian M.
10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna

Holiday Home in Sussex

9.8 out of 10, Exceptional, (50)
"Wonderful property. Host was extremely responsive and helpful."
United States
joan r.
Wooded Hills/Indoor Pool/Hot Tub/Arcade

Holiday Home in Oconomowoc

10.0 out of 10, Exceptional, (3)
"The house was absolutely perfect for our group. The backyard was a great area for our group to get together play yard games and be able to enjoy the lake at the same time. For the few hours of rain we experienced, we were able to enjoy the fun arcade games in the basement to pass our time. Oh and how could I forget the indoor pool!Katie was a wonderful host. Great communication and she was readily available to help us on the property if any requests were asked. She is very knowledgeable about...
United States
Billy L.
Kohl Manor Luxury Lake 8-br exclusive retreat Pool, Cinema, Arcade on LacLaBelle

Apartment in Lower East Side

3.0 star property
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

Condo in 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 AU$509
includes taxes & fees
8 Dec - 9 Dec
Downtown Eastside gem near Fiserv Forum Water St Brady St

Holiday Home in River Hills

10.0 out of 10, Exceptional, (3)
"Love the indoor pool and the movie room!"
United States
JOE C.
Spacious 5-bedroom house in awesome River Hills with an INDOOR POOL!

Holiday Home in Riverwest

9.6 out of 10, Exceptional, (77)
"He was very kind!"
United States
Hope
The price is AU$360
includes taxes & fees
8 Dec - 9 Dec
Three bedrooms upstairs

Holiday Home in 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 AU$506
includes taxes & fees
7 Dec - 8 Dec
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

Holiday Home in Bay View

9.6 out of 10, Exceptional, (8)
"Great place!"
United States
Kathy R.
The price is AU$708
includes taxes & fees
14 Dec - 15 Dec
Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers

Holiday Home in 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 AU$2,561
includes taxes & fees
21 Dec - 22 Dec
MKE Mansion - Both Wings

Holiday Home in 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 AU$825
includes taxes & fees
6 Dec - 7 Dec
Stunning Upscale Retreat - Steps From Everything

Holiday Home in Elkhorn

9.6 out of 10, Exceptional, (35)
"Property was clean and the layout is absolutely beautiful."
United States
Daniel C.
LAKEFRONT HIDDEN GEM !

Apartment in Westown

2.0 star property
9.8 out of 10, Exceptional, (6)
"Parking was great"
United States
Margaret S.
Modern Studio Apt with Skywalk to Fiserv, Rooftop, and Parking

Holiday Home in Burnham Park

9.6 out of 10, Exceptional, (252)
"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
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 Waukesha Hotel Reviews

Find out more about Waukesha

Everything you need to know about Waukesha holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Waukesha holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Waukesha holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Waukesha holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Waukesha. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Waukesha holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Waukesha holiday rentals we have selected for you start as low as AU$247 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Waukesha rentals

At Expedia, we put the best Waukesha holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Waukesha rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Waukesha holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Waukesha. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Waukesha?

Yes, there are holiday rentals in Waukesha close to Frame Park Formal Gardens, or you can select a more secluded option if you're looking for a relaxing stay. The shops and live music are just a few reasons why travellers like Waukesha. Make sure you have time to check out the architecture and sporting events during your trip.

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

17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18: This holiday home rental outside of Waukesha offers an indoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 7 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 balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Waukesha?

Expedia has 5 holiday rentals for your stay in Waukesha.

What can I see and do in Waukesha?

Frame Park Formal Gardens and Fox River Park are a couple of scenic spots to enjoy the outdoors, whereas Waukesha County Museum is one of the cultural attractions. While here, Center Court Sports Complex and Waukesha County Expo Center are other places worth a visit.

What are holiday rentals like in Waukesha?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Waukesha. Holiday rentals offer amenities like WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitised environment, a holiday rental can provide a sense of privacy away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for family trips or small group gatherings.