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 Milwaukee
4.97 out of 5 average rating, 89 reviewsThe Peacock Place
10–17 Oct
Home in Menomonee Falls
4.96 out of 5 average rating, 24 reviewsYour Own Spacious Place with a Pool & Peloton
1–8 Feb
Home in Milwaukee
4.88 out of 5 average rating, 17 reviewsCentral Location w/ Skyline View
31 Jan – 7 Feb
Home in Sussex
4.85 out of 5 average rating, 82 reviewsAmazing Five Bedroom Milwaukee Vacation Home!!
26 Sept – 3 Oct
Home in Germantown
4.75 out of 5 average rating, 60 reviewsParadise In Germantown! Swim 365 days indoor pool.
3–10 Jun
Home in Milwaukee
4.97 out of 5 average rating, 60 reviewsUnique House with Indoor Heated Pool & Sauna
8–15 Feb
Home in River Hills
4.95 out of 5 average rating, 39 reviewsExclusive Milwaukee Home
24 Sept – 1 Oct
Home in Waukesha
4.94 out of 5 average rating, 16 reviewsFrank Lloyd Wright style home near Milwaukee
7–14 Apr
Weekly house rentals
Home in Milwaukee
4.98 out of 5 average rating, 60 reviewsEast Side 2nd floor Gem
13–20 May
Home in Milwaukee
5.0 out of 5 average rating, 13 reviewsEntire Cozy Cottage! Pet Friendly, No Cleaning Fee
8–15 Dec
Home in Milwaukee
4.92 out of 5 average rating, 12 reviewsCharming Downtown Flat
17–24 May
Home in Milwaukee
4.97 out of 5 average rating, 31 reviews2BR Sunny Upper Vibrant Bay View - w/ Parking
14–21 Jan
Home in Milwaukee
4.96 out of 5 average rating, 70 reviewsCharming Milwaukee Bungalow Apartment
11–18 Sept
Home in Wauwatosa
4.97 out of 5 average rating, 34 reviewsHartofTosa
2–9 May
Home in Milwaukee
4.92 out of 5 average rating, 64 reviewsClassy MKE River West -Lower
23–30 Oct
Home in Milwaukee
4.96 out of 5 average rating, 27 reviewsUnique creative space in great MKE location!
11–18 Jan
Private house rentals
Home in Shorewood
4.9 out of 5 average rating, 42 reviewsCream City Home - Shorewood
16–23 Mar
Home in Milwaukee
4.91 out of 5 average rating, 22 reviewsQuiet Bay View Getaway
2–9 Nov
Home in Milwaukee
4.94 out of 5 average rating, 49 reviewsRemodeled Apartment in Bayview
5–12 Oct
Home in Saint Francis
4.98 out of 5 average rating, 57 reviewsEden Place
4–11 Jul
Home in Milwaukee
5.0 out of 5 average rating, 7 reviewsLower Level Suite near Brady St
17–24 May
Home in Milwaukee
5.0 out of 5 average rating, 13 reviewsPeriwinkle Place, Bay View
4–11 Jun
Home in Milwaukee
4.98 out of 5 average rating, 56 reviewsHarry’s Hideaway
24–31 Aug
Home in Greendale
4.97 out of 5 average rating, 71 reviewsThe Robin's Roost LLC
1–8 Apr
Quick stats about house rentals in Milwaukee
Total rentals
1.1K 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
33K 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
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