
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.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Milwaukee holiday rentals
Other great holiday rentals in Milwaukee
Guest favourite

Private room in Greenfield
4.91 out of 5 average rating, 331 reviewsSpacious Downstairs Suite/private bathroom
Top guest favourite

Private room in Riverwest
5 out of 5 average rating, 27 reviewsLuxury private room with balcony!
Superhost

Private room in Riverwest
4.86 out of 5 average rating, 69 reviewsThe Native.
Top guest favourite

Private room in Milwaukee
5 out of 5 average rating, 41 reviewsArtsy Digs, private room in home hosted by Johanna
Top guest favourite

Private room in Milwaukee
4.98 out of 5 average rating, 61 reviewsLannon Stone Beauty

Private room in Milwaukee
4.88 out of 5 average rating, 33 reviewsWelcoming stay close to everything
Top guest favourite

Private room in Brookfield
5 out of 5 average rating, 79 reviewsFrank Lloyd Wright: Spring Green Room
Top guest favourite

Private room in Saint Francis
4.96 out of 5 average rating, 287 reviewsGinkgo House has a Room for YOU!
Quick stats about holiday rentals in Milwaukee
Total rentals
2.5K properties
Total number of reviews
107K reviews
Family-friendly rentals
1.5K properties are a good fit for families
Pet-friendly rentals
780 properties allow pets
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
1.4K properties have a dedicated workspace
Destinations to explore
- Downtown Chicago Holiday rentals
- Lake Geneva Holiday rentals
- Madison Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- South Haven Holiday rentals
- Holland Holiday rentals
- Saugatuck Holiday rentals
- South Side Holiday rentals
- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- Chicago Holiday rentals
- Rentals with a fireplace Milwaukee
- Lakehouse rentals Milwaukee
- Fitness-friendly rentals Milwaukee
- Loft rentals Milwaukee
- Pet-friendly rentals Milwaukee
- Waterfront rentals Milwaukee
- Rentals with lake access Milwaukee
- Rentals with pools Milwaukee
- Rentals with a hot tub Milwaukee
- Rentals with an EV charger Milwaukee
- Rentals with a patio Milwaukee
- Rentals with a firepit Milwaukee
- Rentals with a washing machine and dryer Milwaukee
- Rentals with beach access Milwaukee
- Rentals with breakfast Milwaukee
- Mansion rentals Milwaukee
- Family-friendly rentals Milwaukee
- Smoking-friendly rentals Milwaukee
- Apartment rentals Milwaukee
- Rentals with outdoor seating Milwaukee
- House rentals Milwaukee
- Flat rentals Milwaukee
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Six Flags Great America
- Erin Hills Golf Course
- Alpine Valley Resort
- Kohler-Andrae State Park
- Milwaukee Public Museum
- Geneva National Resort & Club
- Illinois Beach State Park
- Harrington Beach State Park
- Bradford Beach
- Grand Geneva Resort & Spa
- Racine North Beach
- Milwaukee County Zoo
- Richard Bong State Recreation Area
- Wilmot Mountain Ski Resort
- The Bull at Pinehurst Farms Golf Course
- Discovery World
- Milwaukee Country Club
- West Bend Country Club
- Springs Water Park
- The Mountain Top Ski & Adventure Center at Grand Geneva
- Heiliger Huegel Ski Club
- Blue Mound Golf and Country Club
- Sunburst
- America's Action Territory