House holiday rentals in Milwaukee
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Top-rated house rentals in Milwaukee
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Milwaukee
House rentals with a pool
Home in Lake Geneva
4.91 out of 5 average rating, 126 reviewsHome away from Home
9–16 Mar
Home in Milwaukee
4.97 out of 5 average rating, 89 reviewsThe Peacock Place
31 Aug – 7 Sep
Home in Milwaukee
4.89 out of 5 average rating, 18 reviewsCentral Location w/ Skyline View
10–17 Apr
Home in Sussex
4.85 out of 5 average rating, 82 reviewsAmazing Five Bedroom Milwaukee Vacation Home!!
1–8 Apr
Home in Delafield
4.96 out of 5 average rating, 23 reviewsCute and cozy 2 bedroom house perfectly located!
21–28 Feb
Home in Caledonia
4.87 out of 5 average rating, 61 reviews7 1/2 ACRES! POOL! HOT TUB! FISHING POND!
30 Sep – 7 Oct
Home in Menomonee Falls
4.96 out of 5 average rating, 24 reviewsYour Own Spacious Place with a Pool & Peloton
18–25 Dec
Home in Germantown
4.75 out of 5 average rating, 60 reviewsParadise In Germantown! Swim 365 days indoor pool.
28 Jun – 5 Jul
Weekly house rentals
Home in West Allis
4.84 out of 5 average rating, 105 reviewsDesigner Cottage with Parking, Patio & Netflix
8–15 Oct
Home in Milwaukee
4.92 out of 5 average rating, 129 reviewsComfortable Home in Quiet MKE Area near AMF/Fiserv
15–22 Dec
Home in Muskego
4.98 out of 5 average rating, 142 reviews3 Bedroom Muskego Home
10–17 Oct
Home in Milwaukee
5.0 out of 5 average rating, 14 reviewsEntire Cozy Cottage! Pet Friendly, No Cleaning Fee
15–22 Dec
Home in Milwaukee
4.92 out of 5 average rating, 64 reviewsClassy MKE River West -Lower
31 Mar – 7 Apr
Home in Milwaukee
4.96 out of 5 average rating, 71 reviewsCharming Milwaukee Bungalow Apartment
10–17 Sep
Home in Milwaukee
4.92 out of 5 average rating, 13 reviewsCharming Downtown Flat
17–24 Oct
Home in Milwaukee
4.91 out of 5 average rating, 22 reviewsQuiet Bay View Getaway
27 Nov – 4 Dec
Private house rentals
Home in Saint Francis
4.98 out of 5 average rating, 58 reviewsEden Place
2–9 Jul
Home in Shorewood
4.97 out of 5 average rating, 73 reviewsShorewood house - near shops w/ WiFi & parking
28 Nov – 5 Dec
Home in Milwaukee
5.0 out of 5 average rating, 25 reviewsCharming Milwaukee Bungalow 10 min from Everything
30 Aug – 6 Sep
Home in Milwaukee
4.97 out of 5 average rating, 32 reviews2BR Sunny Upper Vibrant Bay View - w/ Parking
20–27 Oct
Home in Greendale
4.97 out of 5 average rating, 73 reviewsThe Robin's Roost LLC
2–9 Apr
Home in Milwaukee
5.0 out of 5 average rating, 7 reviewsLower Level Suite near Brady St
11–18 May
Home in Milwaukee
4.98 out of 5 average rating, 56 reviewsHarry’s Hideaway
7–14 Oct
Home in Wauwatosa
4.87 out of 5 average rating, 23 reviewsThe Swan Dive | Tosa Art Loft
11–18 Jun
Quick stats about house rentals in Milwaukee
Total rentals
1.1T properties
Rentals with dedicated workspaces
640 properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
360 properties allow pets
Family-friendly rentals
840 properties are a good fit for families
Total number of reviews
33T reviews
Destinations to explore
- Downtown Chicago Holiday rentals
- Madison Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
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