Waukesha Vacation Rentals

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Dec 7 - Dec 8
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Dec 8 - Dec 9
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Dec 12 - Dec 14
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Dec 19 - Dec 21

Vacation Rentals in Waukesha

3 bedrooms, iron/ironing board, free WiFi, bed sheets
Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub

Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub

Waukesha
9.8 out of 10, Exceptional, (16)
"Will come and stay again great host and home"
United States
Dion S.
$269 nightly
The price is $304
Dec 9 - Dec 10
Total with taxes and fees
Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub
Premier Room, 1 King Bed | Iron/ironing board, free WiFi, bed sheets
The Plaza Hotel

The Plaza Hotel

3.0 star property
Downtown Milwaukee
8.8 out of 10, Excellent, (1153)
"Loved this hotel! Clean friendly and cute!!"
United States
Sharon H
$157 nightly
The price is $186
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Plaza Hotel
Fireplace
Kasa Westown Milwaukee

Kasa Westown Milwaukee

4.0 star property
Westown
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
$173 nightly
The price is $204
Dec 10 - Dec 11
Total with taxes and fees
Kasa Westown Milwaukee
Billiards
ROVE LIVING/KL - Malt House

ROVE LIVING/KL - Malt House

4.0 star property
Westown
8.8 out of 10, Excellent, (10)
"Loved the uniqueness, location and cleanliness of the unit."
United States
Teresa
$138 nightly
The price is $163
Dec 10 - Dec 11
Total with taxes and fees
ROVE LIVING/KL - Malt House
Terrace/patio
17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18

17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18

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.
$1,867 nightly
The price is $2,110
Dec 14 - Dec 15
Total with taxes and fees
17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18
Outdoor pool, a heated pool
7 1/2 Acre Estate, Fish Pond, Events! Weddings, MSG Owner for discounts!!!

7 1/2 Acre Estate, Fish Pond, Events! Weddings, MSG Owner for discounts!!!

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.
$615 nightly
The price is $648
Dec 21 - Dec 22
Total with taxes and fees
7 1/2 Acre Estate, Fish Pond, Events! Weddings, MSG Owner for discounts!!!
Indoor pool, a heated pool
10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna

10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna

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
Fridge, microwave, oven, stovetop
Wooded Hills/Indoor Pool/Hot Tub/Arcade

Wooded Hills/Indoor Pool/Hot Tub/Arcade

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
Dining room
ROVE LIVING/KB - Prospect

ROVE LIVING/KB - Prospect

3.0 star property
Lower East Side
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
Dining
Kohl Manor Luxury Lake 8-br exclusive retreat Pool, Cinema, Arcade on LacLaBelle

Kohl Manor Luxury Lake 8-br exclusive retreat Pool, Cinema, Arcade on LacLaBelle

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
Exterior
Downtown Eastside gem near Fiserv Forum Water St Brady St

Downtown Eastside gem near Fiserv Forum Water St Brady St

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.
$282 nightly
The price is $332
Dec 8 - Dec 9
Total with taxes and fees
Downtown Eastside gem near Fiserv Forum Water St Brady St
Dining
Three bedrooms upstairs

Three bedrooms upstairs

Riverwest
9.6 out of 10, Exceptional, (77)
"He was very kind!"
United States
Hope
$200 nightly
The price is $235
Dec 8 - Dec 9
Total with taxes and fees
Three bedrooms upstairs
Dining
Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers

Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers

Bay View
9.6 out of 10, Exceptional, (8)
"Great place!"
United States
Kathy R.
$393 nightly
The price is $463
Dec 14 - Dec 15
Total with taxes and fees
Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers
Fridge, microwave, oven, stovetop
Stunning Upscale Retreat - Steps From Everything

Stunning Upscale Retreat - Steps From Everything

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.
$458 nightly
The price is $539
Dec 8 - Dec 9
Total with taxes and fees
Stunning Upscale Retreat - Steps From Everything
Outdoor dining
MKE Mansion - Both Wings

MKE Mansion - Both Wings

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.
$1,484 nightly
The price is $1,673
Dec 21 - Dec 22
Total with taxes and fees
MKE Mansion - Both Wings
Balcony
LAKEFRONT HIDDEN GEM !

LAKEFRONT HIDDEN GEM !

Elkhorn
9.6 out of 10, Exceptional, (35)
"Property was clean and the layout is absolutely beautiful."
United States
Daniel C.
LAKEFRONT HIDDEN GEM !
Exterior
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

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.
$283 nightly
The price is $334
Dec 8 - Dec 9
Total with taxes and fees
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!
Dining
Frank Lloyd Wright-Designed House In Milwaukee, WI, 4 Bed 2.5 Bath, Sleep10

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

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
Interior
Spacious 5-bedroom house in awesome River Hills with an INDOOR POOL!

Spacious 5-bedroom house in awesome River Hills with an INDOOR POOL!

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!
Dining
Island view cottage on crystal clear spring fed lake.

Island view cottage on crystal clear spring fed lake.

Burlington
10.0 out of 10, Exceptional, (146)
"This home on Brown’s Lake checks every box. It is spacious with plenty of space for 12 of us (9 adults and 3 kids) to spread out. The newly remodeled kitchen is amazing (nicer than mine at home) and has every dish, pot, pan or utensil you could ever need. A screened-in 3 season room is off the kitchen with wonderful views of the lake. There are two master bedrooms, but all of the bedrooms are spacious and are located near bathrooms that are lovely. Everyone in our group had their own space...
United States
Linda C.
Island view cottage on crystal clear spring fed lake.
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

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

10/10 Excellent
"Clean and nice staff"
Darlene 1-night trip
Posted 2 days ago
Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

Find out more about Waukesha

Everything you need to know about Waukesha vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Waukesha vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Waukesha vacation 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 low season months. For more hustle and bustle, you may prefer to visit Waukesha in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $163 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Waukesha rentals

At Expedia, we put the best Waukesha vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Waukesha?

Yes, there are vacation rentals in Waukesha near 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 travelers like Waukesha. Make sure you have time to check out the architecture and sporting events during your trip.

What's the top vacation rental that Waukesha has to offer?

17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18: This vacation home rental outside of Waukesha offers an indoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Waukesha?

Expedia has 5 vacation 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 vacation rentals like in Waukesha?

Vacation rentals are privately owned properties you can reserve for several days or more in Waukesha. Vacation rentals feature extras like WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from public hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for a family trip or a small group gathering.