Pewaukee Holiday Rentals

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Holiday Rentals in Pewaukee

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 NZ$294
includes taxes & fees
4 Jan - 5 Jan 2026
The Plaza Hotel

Aparthotel in Westown

4.0 star property
9.0 out of 10, Wonderful, (118)
"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

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 NZ$285
includes taxes & fees
10 Dec - 11 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 NZ$3,653
includes taxes & fees
17 Dec - 18 Dec
17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18

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

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

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

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 NZ$576
includes taxes & fees
9 Dec - 10 Dec
Downtown Eastside gem near Fiserv Forum Water St Brady St

Holiday Home in Riverwest

9.6 out of 10, Exceptional, (77)
"He was very kind!"
United States
Hope
The price is NZ$407
includes taxes & fees
9 Dec - 10 Dec
Three bedrooms upstairs

Holiday Home in Bay View

9.6 out of 10, Exceptional, (8)
"Great place!"
United States
Kathy R.
The price is NZ$802
includes taxes & fees
14 Dec - 15 Dec
Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers

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 NZ$934
includes taxes & fees
9 Dec - 10 Dec
Stunning Upscale Retreat - Steps From Everything

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 NZ$2,897
includes taxes & fees
21 Dec - 22 Dec
MKE Mansion - Both Wings

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 NZ$578
includes taxes & fees
9 Dec - 10 Dec
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

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

Holiday Home in River Hills

8.0 out of 10, Very good, (4)
"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 Lower East Side

2.0 star property
9.8 out of 10, Exceptional, (19)
"Great property for our family group for a long weekend in Milwaukee. "
United States
Karl S.
The price is NZ$736
includes taxes & fees
9 Dec - 10 Dec
NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms

Holiday Home in Hartford

10.0 out of 10, Exceptional, (5)
"This is a nice place to stay. The bedrooms are all spacious, clean and very comfy. The communication with the host was great. I would stay here again. "
United States
Nicole D.
The price is NZ$1,404
includes taxes & fees
10 Dec - 11 Dec
Luxury 5BR 3.5B sleeps 17 w/ Hot Tub, Home Theater near Skiing, Golf, & Bars

Holiday Home in Waukesha

9.8 out of 10, Exceptional, (16)
"Awesome place - would definitely stay again! "
United States
Anonymous traveller
Magnificently restored, charming, 8+ Bed-Victorian on a beautiful 1.5 acres.

Holiday Home in Lower East Side

9.6 out of 10, Exceptional, (66)
"Dustin was a great host! Very easy to communicate with and the house was great as well, thanks much!"
United States
Lisa M.
The price is NZ$724
includes taxes & fees
9 Dec - 10 Dec
Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find

Holiday Home in Downtown Milwaukee

10.0 out of 10, Exceptional, (5)
"Enjoyed stay at this nice home "
United States
Eduardo P.
The price is NZ$463
includes taxes & fees
9 Dec - 10 Dec
Remodeled Home - Steps from Brady Street!
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 Pewaukee Hotel Reviews

Find out more about Pewaukee

Everything you need to know about Pewaukee 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 Pewaukee 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 Pewaukee holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Pewaukee holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pewaukee. 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pewaukee 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 Pewaukee holiday rentals we have selected for you start as low as NZ$285 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pewaukee rentals

At Expedia, we put the best Pewaukee 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 Pewaukee 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 Pewaukee 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 Pewaukee. 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 Pewaukee?

Yes, there are holiday rentals in Pewaukee close to Springs Water Park, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and water parks in Pewaukee. Make sure you have time to check out the sporting events and lake views during your trip.

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

17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18: This holiday home rental outside of Pewaukee 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 Pewaukee?

Choose from 21 Expedia holiday rentals in Pewaukee for a memorable holiday.

What’s there to see and do in Pewaukee?

Pewaukee Lake and Pewaukee Lake Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Springs Water Park. Nagawaukee County Park and Beach and Two Brothers Wines are other places to visit while you're in town.

What’s a holiday rental in Pewaukee like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Pewaukee. Holiday rentals feature extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family getaway.