Vacation rentals with a pool in Milwaukee County

Find and book unique homes with a pool on Airbnb

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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, 129 reviews

The Gem of Brewers Hill w/hot tub & seasonal pool

JosephRating, 5 stars3 weeks ago
Amazing and beautiful home! Will definitely look at staying here again when back in Milwaukee! Thank you again!
Home in River Hills
4.95 out of 5 average rating, 42 reviews

Exclusive Milwaukee Home

MaryRating, 5 stars7 months ago
The linens on the beds were soft. There were plenty of bath towels and pool towels. The kitchen was absolutely complete but coffee maker worked painfully slow. The house was huge and comfortable for my family reunion with my adult kids and their families. The grocery store was quite close. The property had a nice yard for the toddlers to run. The pool was very big especially for a private pool. It had a nice configuration; a very deep end with a diving board for the Dads and a nice shallow end with steps for the kids. The pool was heated and we were able to stay in it all day comfortably to play. Xee always responded quickly with answers. I would definitely stay there again.
Home in Cudahy
4.77 out of 5 average rating, 150 reviews

Make Yourself At Home! Close to Lake & Airport!

VictoriaRating, 5 stars1 month ago
Where do I start :) it’s the best air b n b Ever . We stayed here multiple times and it is our favorite! Every time we need a place to stay when we are in Milwaukee this is first choice!
Top guest favorite
Home in Milwaukee
4.97 out of 5 average rating, 161 reviews

The Peacock Place w/ Outdoor Heated Pool

EmilyRating, 5 stars1 week ago
I have traveled to many places and stayed in many hotels and AirBNB’s, and the Peacock house was my absolute favorite! Stephanie and Jesse were incredibly sweet, offered places to go to for the kids, and even greeted us with a friendly hello! The house was even better than the photos! For those that like vintage, antique, and unique style…this house will not disappoint you. Not to mention that the furniture and bedding was unbelievably comfortable. We have already discussed coming back again because we didn’t get enough time in Milwaukee. When we do, we sure hope the Peacock house is available!
Top guest favorite
Home in Milwaukee
5 out of 5 average rating, 9 reviews

Big BLUE Skyline VIEW

KelseyRating, 5 stars3 months ago
We had an Airbnb that fell through and needed a new place within minutes. Dave and Cathy’s place was available for instant book and we had no problems getting in! The space was beautiful and fully equipped with everything we could need. Truly so happy and grateful for this space! We decided we’d love to stay here any time we’re visiting Milwaukee. Couldn’t recommend enough!
Superhost
Home in Milwaukee
4.92 out of 5 average rating, 24 reviews

Central Location w/ Skyline View

ShanitaRating, 5 stars7 months ago
Great and super responsive hosts. place was in the prefect location to experience the city without being in a busy or noisy area. We would love to stay here again in the future!
Home in Milwaukee
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