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

Home in Brewer's Hill
4.92 out of 5 average rating, 140 reviewsThe Gem of Brewers Hill w/hot tub & seasonal pool
GerryRating, 5 stars4 weeks ago
Excellent location and plenty of beds and bathrooms.
Guest favorite

Home in Racine
4.89 out of 5 average rating, 27 reviewsNautical Escape •Spacious Home•Pool /Cedar Hot Tub
EmilyRating, 5 stars2 weeks ago
We loved the pool and quiet neighborhood. Check-in was easy - Matt let us know we could check in early at 1. The hot tub wasn't heating up all the way so we contacted Matt and he came over and fixed it within 10 minutes. He was very responsive and attentive. We had everything we needed and it was a nice space to have a few friends over and hang out in the pool. The hot tub was nice, very comfortable to sit in and heated up quickly. Overall we had a great experience and would visit again, for sure!
Superhost

Home in Sussex
4.88 out of 5 average rating, 112 reviewsWooded Hills/Indoor Pool/Hot Tub/Arcade
KaitlynRating, 5 stars3 weeks ago
Great stay. Pool could have been cleaned better before our stay.

Home in Caledonia
4.85 out of 5 average rating, 75 reviews7 1/2 Acres! Pool! Hot Tub! Fishing Pond!
SherriRating, 5 stars3 months ago
I think this was my favorite place I’ve rented. I’m glad I found it just an hour outside the suburbs of Chicago. It’s a country feel with a ton of activities as described, plus a few extra. My boys really enjoyed the game room. There’s a TV so we played music videos while playing darts, billiards, and I enjoyed throw back video games like Donkey Kong, Centipede and Dig dug. It was cooler outside so I definitely want to return in the summer to enjoy the pool, bonfire, fishing pond, but we had one nice day so still got to enjoy the large property, paddle boat, swings, bocce ball and hot tub. The house has very comfortable furniture, like the beds and couches. We watched movies at night and slept well. Robert was a great host and I appreciated all the helpful notes around the house. I almost felt guilty it was just me and my boys, but it was a perfect getaway. Plenty to do, or do nothing and enjoy the views.
Guest favorite

Home in Cudahy
4.78 out of 5 average rating, 152 reviewsMake Yourself At Home! Close to Lake & Airport!
TanyaRating, 5 stars3 months 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 Brewer's Hill
4.97 out of 5 average rating, 177 reviewsThe Peacock Place w/ Seasonal Outdoor Heated Pool
GregRating, 5 stars1 day ago
Unlike most Airbnb’s that I’ve stayed at, we got to meet our host, Stephanie in person just by chance. She was so lovely and made sure that everything was OK for our stay. The home was comfortable, clean, spacious, and close to everything we needed. What a wonderful home for our vacation!
Guest favorite

Home in Riverwest
4.92 out of 5 average rating, 26 reviewsCentral Location w/ Skyline View
CieraRating, 5 stars3 months ago
Cute place! Stayed here for a couple months. Dave and Cathy were very friendly and welcoming and quick to fix any issues.

Home in Milwaukee
Townhome Villa private oasis
Quick stats about vacation rentals with a pool in Milwaukee
Total rentals
40 properties
Nightly prices starting at
G$8,368 GYD before taxes and fees
Total number of reviews
950 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Six Flags Great America
- Erin Hills Golf Course
- Milwaukee Public Museum
- Alpine Valley Resort
- Kohler-Andrae State Park
- Geneva National Resort & Club
- Illinois Beach State Park
- Racine North Beach
- Bradford Beach
- Grand Geneva Resort & Spa
- Milwaukee County Zoo
- Richard Bong State Recreation Area
- Wilmot Mountain Ski Resort
- Harrington Beach State Park
- Milwaukee Country Club
- The Bull at Pinehurst Farms Golf Course
- West Bend Country Club
- Heiliger Huegel Ski Club
- Springs Water Park
- Discovery World
- The Mountain Top Ski & Adventure Center at Grand Geneva
- America's Action Territory
- Blue Mound Golf and Country Club
- Sunburst