
Holiday houses in Milwaukee
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Milwaukee
Guests agree: these stays are highly rated for location, cleanliness and more.
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Popular amenities for Milwaukee holiday rentals
Other great holiday rentals in Milwaukee
Guest favourite

Home in Muskego
4.88 out of 5 average rating, 110 reviewsMuskego Hideaway on 2 Acre Lot
JadeRating, 5 stars4 days ago
Jeff & Julie were quick to respond to our questions, before arriving and upon arrival. Easy access to grocery store, gas station, restaurants, interstate. Private location & plenty of space for our party & number of guests. You guys were great & your Airbnb provided a nice place for us all to be able to stay together. Thanks for being wonderful hosts!
Superhost

Apartment in Wauwatosa
4.92 out of 5 average rating, 13 reviews10 Minutes from Downtown! The Highlands Hideaway
ReginaRating, 5 stars3 weeks ago
Very clean and the host was very responsive. Great area with a lot of close restaurants.
Guest favourite

Farm stay in Germantown
4.97 out of 5 average rating, 98 reviewsLace & Woods Farm "Hammer Hideaway"
RoryRating, 5 stars1 month ago
Such an enchanting stay. The hosts and resident animals were friendly. My family loved the barn cats that snuck their way to us - especially Carl. The wood fireplace added to the coziness. Everything was clean, comfortable, and heat moves well throughout the space. My mother-in-law is already planning our next visit come spring!
Superhost

Home in Milwaukee
4.44 out of 5 average rating, 9 reviewsThe Ultimate Family Suite 2! (Right unit)
JeffreyRating, 5 stars3 months ago
Great peaceful place that’s not too far from all the fun in Milwaukee.
Guest favourite

Home in Mequon
4.92 out of 5 average rating, 60 reviewsMequon Wedding Retreat
LianeRating, 5 stars3 months ago
David met us for check in and walked through everything! Throughout the reservation process and when we left he was very responsive. It was a beautiful home!!
Superhost

Apartment in Milwaukee
4.65 out of 5 average rating, 37 reviews*NEW* By Beach, Great Value, on Murray Ave!
NicholasRating, 5 stars6 days ago
Laura was a great host. She was helpful when we needed to change the days we were staying and provided clear instructions before arrival. The location is great as it is near the upper east side and east access to downtown. Would definitely stay here again!
Guest favourite

Home in Lower East Side
4.91 out of 5 average rating, 55 reviewsWalk to Brady St-Family Friendly-Modern Victorian
JaclynRating, 5 stars6 days ago
What an incredible stay! Clean, cozy, and in an incredible location. I would highly recommend Leah’s place for any group looking for a place to stay in Milwaukee. It was fully equipped with all the amenities we needed and the backyard is beautiful.
Guest favourite

Home in Wauwatosa
5 out of 5 average rating, 23 reviewsThe Mayfair Midcentury
SusanRating, 5 stars1 month ago
This was perfect for our family for Christmas. The kitchen was perfect for cooking our Christmas dinner. The table was a little small and could only seat 4, but the kitchen had seating at the countertop. Overall, lovely home.
Quick stats about holiday rentals in Milwaukee
Total rentals
2.5K properties
Total number of reviews
107K reviews
Family-friendly rentals
1.5K properties are a good fit for families
Pet-friendly rentals
800 properties allow pets
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
1.4K properties have a dedicated workspace
Destinations to explore
- Downtown Chicago Holiday rentals
- Madison Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- Lake Michigan Beach Holiday rentals
- South Side Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Oshkosh Holiday rentals
- Chicago Holiday rentals
- Smoking-friendly rentals Milwaukee
- Hotel rentals Milwaukee
- Waterfront rentals Milwaukee
- Rentals with a hot tub Milwaukee
- Rentals with a fireplace Milwaukee
- Rentals with breakfast Milwaukee
- Mansion rentals Milwaukee
- Townhouse rentals Milwaukee
- Rentals with beach access Milwaukee
- Pet-friendly rentals Milwaukee
- Loft rentals Milwaukee
- Apartment rentals Milwaukee
- Rentals with a fire pit Milwaukee
- Rentals with a washing machine and dryer Milwaukee
- Rentals with lake access Milwaukee
- Monthly Rentals Milwaukee
- Rentals with an EV charger Milwaukee
- Private suite rentals Milwaukee
- Lakehouse rentals Milwaukee
- Fitness-friendly rentals Milwaukee
- Rentals with outdoor seating Milwaukee
- Condo rentals Milwaukee
- Rentals with a patio Milwaukee
- Kid-friendly rentals Milwaukee
- Rentals with pools Milwaukee
- House rentals Milwaukee
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