Holiday houses in Milwaukee
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Top-rated holiday rentals in Milwaukee
Guests agree: these stays are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Milwaukee holiday rentals
Other great holiday rentals in Milwaukee
Guest suite in Brookfield
4.99 out of 5 average rating, 184 reviewsIn the Canopy (beautiful Brookfield/Milwaukee)
16–23 Sep
Home in Wauwatosa
4.98 out of 5 average rating, 178 reviewsWauwatosa/Milwaukee 10 Minutes from Downtown
3–10 Apr
Guesthouse in Milwaukee
4.86 out of 5 average rating, 274 reviewsCozy Brewer's Hill Coach House
10–17 Jan
Guest suite in Brookfield
4.88 out of 5 average rating, 107 reviewsFamily Friendly - Entire Guest suite
9–16 Aug
Home in Milwaukee
4.98 out of 5 average rating, 194 reviewsSunny Upper Flat in Shorewood Near UWM & Downtown
14–21 Oct
Apartment in Milwaukee
4.97 out of 5 average rating, 369 reviewsNewly remodeled Chic-Hip apartment-Downtown area
17–24 Sep
Home in Milwaukee
5.0 out of 5 average rating, 38 reviewsBright 1 Bed in the heart of Bay View - w/ Parking
3–10 Dec
Home in Milwaukee
5.0 out of 5 average rating, 15 reviewsEntire Cozy Cottage! Pet Friendly, No Cleaning Fee
20–27 Nov
Quick stats about holiday rentals in Milwaukee
Total rentals
2.4K properties
Rentals with dedicated workspaces
1.4K properties have a dedicated workspace
Rentals with a pool
50 properties have a pool
Pet-friendly rentals
770 properties allow pets
Family-friendly rentals
1.5K properties are a good fit for families
Total number of reviews
94K reviews
Destinations to explore
- Downtown Chicago Holiday rentals
- Madison Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- Schaumburg Holiday rentals
- Chicago Holiday rentals
- Fitness-friendly rentals Milwaukee
- Waterfront rentals Milwaukee
- Rentals with a patio Milwaukee
- Apartment rentals Milwaukee
- Condo rentals Milwaukee
- Rentals with a washing machine and dryer Milwaukee
- Pet-friendly rentals Milwaukee
- Rentals with a fire pit Milwaukee
- House rentals Milwaukee
- Rentals with outdoor seating Milwaukee
- Hotel rentals Milwaukee
- Rentals with a fireplace Milwaukee
- Monthly Rentals Milwaukee
- Private suite rentals Milwaukee
- Rentals with beach access Milwaukee
- Mansion rentals Milwaukee
- Kid-friendly rentals Milwaukee
- Cottage rentals Milwaukee
- Rentals with lake access Milwaukee
- Loft rentals Milwaukee
- Rentals with an EV charger Milwaukee
- Lakehouse rentals Milwaukee
- Cabin rentals Milwaukee
- Smoking-friendly rentals Milwaukee
- Rentals with pools Milwaukee
- Rentals with a hot tub Milwaukee
- Rentals with breakfast Milwaukee
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