Holiday rentals 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
Home in West Allis
4.97 out of 5 average rating, 160 reviewsNear to all Milwaukee favorites/ Free Parking/WiFi
24 Nov – 1 Dec
Home in Milwaukee
5.0 out of 5 average rating, 13 reviewsEntire Cozy Cottage! Pet Friendly, No Cleaning Fee
8–15 Dec
Flat in Milwaukee
5.0 out of 5 average rating, 30 reviewsThird Ward Mojo Dojo Casa Condo
5–12 Sep
Home in Milwaukee
4.96 out of 5 average rating, 70 reviewsCharming Milwaukee Bungalow Apartment
8–15 Sep
Flat in Mequon
4.97 out of 5 average rating, 89 reviewsPrivate Entrance, Patio & Hot Tub -No Shared Space
27 May – 3 Jun
Home in Milwaukee
5.0 out of 5 average rating, 36 reviewsBright 1 Bed in the heart of Bay View - w/ Parking
4–11 Nov
Home in Milwaukee
4.95 out of 5 average rating, 86 reviewsHistorical Brewers Hill Single Family Home
9–16 May
Home in Milwaukee
4.96 out of 5 average rating, 27 reviewsUnique creative space in great MKE location!
29 Jan – 5 Feb
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
- Monthly Rentals Milwaukee
- Smoking-friendly rentals Milwaukee
- Rentals with outdoor seating Milwaukee
- Rentals with an EV charger Milwaukee
- Loft rentals Milwaukee
- Rentals with a firepit Milwaukee
- Rentals with a fireplace Milwaukee
- Hotel rentals Milwaukee
- Rentals with beach access Milwaukee
- Rentals with a patio Milwaukee
- Rentals with lake access Milwaukee
- Rentals with a washing machine and dryer Milwaukee
- Private suite rentals Milwaukee
- Cottage rentals Milwaukee
- Rentals with a hot tub Milwaukee
- Waterfront rentals Milwaukee
- Family-friendly rentals Milwaukee
- House rentals Milwaukee
- Rentals with pools Milwaukee
- Pet-friendly rentals Milwaukee
- Lakehouse rentals Milwaukee
- Flat rentals Milwaukee
- Mansion rentals Milwaukee
- Fitness-friendly rentals Milwaukee
- Rentals with breakfast Milwaukee
- Apartment rentals Milwaukee
- Cabin rentals Milwaukee
- Yurt Rentals United States
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- Holiday Chalets United Kingdom
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- Big House Rentals United States
- Big Cottages Australia
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- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
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- Beach Condos United States
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- Beach Houses United Kingdom
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- Pet-Friendly Vacation Rentals United States
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- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom