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 Menomonee Falls
4.96 out of 5 average rating, 24 reviewsYour Own Spacious Place with a Pool & Peloton
1–8 Feb
Home in Milwaukee
4.97 out of 5 average rating, 88 reviewsThe Peacock Place
29 Dec – 5 Jan
Home in Milwaukee
4.88 out of 5 average rating, 17 reviewsCentral Location w/ Skyline View
30 Jan – 6 Feb
Home in Germantown
4.75 out of 5 average rating, 60 reviewsParadise In Germantown! Swim 365 days indoor pool.
3–10 Jun
Home in Sussex
4.85 out of 5 average rating, 82 reviewsAmazing Five Bedroom Milwaukee Vacation Home!!
28 Mar – 4 Apr
Home in Milwaukee
4.97 out of 5 average rating, 60 reviewsUnique House with Indoor Heated Pool & Sauna
7–14 Feb
Home in River Hills
4.95 out of 5 average rating, 39 reviewsExclusive Milwaukee Home
20–27 Sep
Home in Waukesha
4.94 out of 5 average rating, 16 reviewsFrank Lloyd Wright style home near Milwaukee
6–13 Apr
Weekly house rentals
Home in Muskego
4.81 out of 5 average rating, 181 reviewsLake Muskego House, Walk to Stores & Restaurants
9–16 Dec
Home in Muskego
4.98 out of 5 average rating, 142 reviews3 Bedroom Muskego Home
22–29 Mar
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
4.98 out of 5 average rating, 60 reviewsEast Side 2nd floor Gem
13–20 May
Home in Wauwatosa
4.97 out of 5 average rating, 33 reviewsHartofTosa
2–9 May
Home in Milwaukee
4.92 out of 5 average rating, 63 reviewsClassy MKE River West -Lower
26 Oct – 2 Nov
Home in Milwaukee
4.92 out of 5 average rating, 12 reviewsCharming Downtown Flat
21–28 Dec
Home in Saint Francis
4.98 out of 5 average rating, 57 reviewsEden Place
12–19 Oct
Private house rentals
Home in Milwaukee
4.97 out of 5 average rating, 31 reviewsStylish & Modern Apartment in Bay View - King Bed!
8–15 May
Home in Milwaukee
5.0 out of 5 average rating, 24 reviewsCharming Milwaukee Bungalow 10 min from Everything
26 Aug – 2 Sep
Home in West Allis
5.0 out of 5 average rating, 29 reviewsPet Friendly, Calm + Near It All
20–27 May
Home in Milwaukee
4.9 out of 5 average rating, 21 reviewsQuiet Bay View Getaway
30 Dec – 6 Jan
Home in Milwaukee
5.0 out of 5 average rating, 13 reviewsPeriwinkle Place, Bay View
4–11 Jun
Home in West Allis
4.92 out of 5 average rating, 13 reviewsGreen Valley Homes - Updated Lower Apartment
27 Mar – 3 Apr
Home in Milwaukee
4.88 out of 5 average rating, 98 reviewsCheerful-Quiet 2-bedroom Bungalow
2–9 Aug
Home in Milwaukee
4.98 out of 5 average rating, 56 reviewsHarry’s Hideaway
29 Aug – 5 Sep
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
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