Vacation rentals with a pool in Milwaukee

Find and book unique homes with a pool on Airbnb

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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 reviews

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

GerryRating, 5 stars4 weeks ago
Excellent location and plenty of beds and bathrooms.
Guest favorite
A spacious backyard is showcased with a sparkling blue pool surrounded by lush greenery. A set of steps leads into the shallow end of the pool, while a lounge chair sits nearby, inviting relaxation in a tranquil outdoor setting.
Home in Racine
4.89 out of 5 average rating, 27 reviews

Nautical 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
A spacious indoor pool area is showcased, featuring a large, well-maintained pool surrounded by smooth flooring and exposed stone walls. Wooden beams and decorative lighting add character to the space, while comfortable seating areas and bar stools offer ample places to relax.
Home in Sussex
4.88 out of 5 average rating, 112 reviews

Wooded Hills/Indoor Pool/Hot Tub/Arcade

KaitlynRating, 5 stars3 weeks ago
Great stay. Pool could have been cleaned better before our stay.
Aerial view of the property highlights a spacious backyard featuring a heated pool, patio area, and various trees. A trampoline is visible on the left side, with a deck area providing access to the home. The property is partially fenced, offering a sense of privacy.
Home in Caledonia
4.85 out of 5 average rating, 75 reviews

7 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
An outdoor patio space is presented, featuring a paved area surrounded by various seating options, including green chairs and a red umbrella. A grilling station is visible, and the background includes a garage with an open door. Lush greenery provides a natural border.
Home in Cudahy
4.78 out of 5 average rating, 152 reviews

Make 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 reviews

The 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
A city skyline is visible in the distance, framed by lush green trees. A low stone wall borders the foreground, providing a clear view of the urban landscape and buildings. The scene conveys a blend of nature and city life.
Home in Riverwest
4.92 out of 5 average rating, 26 reviews

Central 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.
An inviting indoor pool area features a crystal-clear pool with stairs leading in. A spacious seating area, furnished with colorful lounge chairs, is positioned nearby. Large windows allow natural light to illuminate the space, complemented by wooden beams on the ceiling.
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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