
Vacation rentals with a pool in Milwaukee County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Milwaukee County
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
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Popular amenities for Milwaukee County rentals with a pool
House rentals with a pool
Guest favorite

Home in Milwaukee
4.92 out of 5 average rating, 133 reviewsThe Gem of Brewers Hill w/hot tub & seasonal pool
ChrisRating, 5 stars1 week ago
It was in a great location to walk to restaurants and brew pubs. There was enough room for everyone (five adults), and we all appreciated that it had several bathrooms. The rec room was very cute. Overall it was a comfortable place to stay, quite, roomy and it had off-street parking which is a plus.

Home in Cudahy
4.78 out of 5 average rating, 152 reviewsMake Yourself At Home! Close to Lake & Airport!
TanyaRating, 5 stars1 month ago
Ann went above and beyond to be a fantastic host!!! Her listing gives a very accurate overview of the living space and what to expect during this airbnb experience. She makes you feel at home and like you're staying at a friend or family member's house vs. an impersonal hotel. Her wonderful pets are an added bonus. There was a furry welcoming committee there to meet us at the door and to offer snuggles :) I would recommend this airbnb to anyone! It's in a peaceful neighborhood and only a short drive to shopping centers and restaurants galore.
Top guest favorite

Home in Milwaukee
4.97 out of 5 average rating, 166 reviewsThe Peacock Place w/ Seasonal Outdoor Heated Pool
AlmaRating, 5 stars1 week ago
Enjoyed our stay there, very comfortable and homey, well equipped, good location, hosts very responsive.
Guest favorite

Home in Milwaukee
4.85 out of 5 average rating, 13 reviewsBig BLUE Skyline VIEW
PersephonaeRating, 5 stars3 weeks ago
Stayed for a convention, it was great having space to come back to instead of a tiny hotel room, and everything was super convenient.
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- Milwaukee Public Museum
- Racine North Beach
- Wilmot Mountain Ski Resort
- Kohler-Andrae State Park
- Erin Hills Golf Course
- Milwaukee Country Club
- The Bull at Pinehurst Farms Golf Course
- Alpine Valley Resort
- Springs Water Park
- Illinois Beach State Park
- Harrington Beach State Park
- Richard Bong State Recreation Area
- Heiliger Huegel Ski Club
- Bradford Beach
- Milwaukee County Zoo
- West Bend Country Club
- Sunburst
- America's Action Territory
- Blue Mound Golf and Country Club
- Discovery World
- Pine Hills Country Club
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