Holiday 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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Guest favourite

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.

Home in Caledonia

4.85 out of 5 average rating, 75 reviews

7 1/2 Acres! Pool! Hot Tub! Fishing Pond!

SherriRating, 5 stars2 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 favourite

Home in Mequon

5 out of 5 average rating, 10 reviews

Vacation home: heated inground pool on 4+ acres

AvremiRating, 5 stars1 month ago

Was a wonderful stay at the home, will definitely go back again in the summer for a nice swim in the beautiful pool! If you are looking for a little getaway in a quiet area with a home that's both comfortable and modern I highly recommend this stay!

Top guest favourite

Home in Brewer's Hill

4.97 out of 5 average rating, 176 reviews

The Peacock Place w/ Seasonal Outdoor Heated Pool

LisaRating, 5 stars5 days ago

Stephanie and Jesse were excellent hosts! They were very easy to get in touch with and, while they stay in the apartment upstairs, we never felt intruded upon. The pool is across the street, but with small kids with us, that actually was a bonus safety feature. It is very easy to get to and our hosts were easy to get in touch with when we needed help with access. The place is super cute and had everything we needed. Love the decor and vibes!

Guest favourite

Farm stay in Germantown

4.97 out of 5 average rating, 99 reviews

Lace & Woods Farm "Hammer Hideaway"

HEATED POOL MAY-SEPT FOR ADDITIONAL CHRG. Cozy designer custom built guest house nestled amongst a 10 acre hobby farm. come for a relaxing getaway. This home is an artistic gem! Boasting an open concept, with a queen bed on main level and twin mattress underneath , a full kitchen, cozy living area, wood burning fireplace. The loft has extra sleeping with a double bed and twin bed.Custom designed. Great location winter and summer, enjoy snowmobiling trails and skiing near by or beaches & hiking

Flat in Brookfield

Rare Find! Indoor Swimming Pool, Pets Allowed!

The property is conveniently situated on the outskirts of Brookfield, far from the hustle and bustle of the city. Put the Milwaukee Public Museum and Harley-Davidson Museum on your to-do list. With the New Berlin Hills Golf Course and Moorland Road Golf Center nearby, golf should also be on your itinerary. Skating is another option, as you can test your skills at the Pettit National Ice Center. Explore the beautiful parks and hiking and biking trails nearby for a reinvigorating experience.

Flat in Brown Deer

New place to stay

Serene Hideaway | Cozy Getaway

Minutes from Froedtert (13 min), Ascension St. Mary’s (15 min), Children’s Hospital (13 min), Aurora Sinai (15 min), VA Hospital (13 min), Columbia St. Mary’s (15 min). Near Cardinal Stritch (10 min), MATC (15 min), Marquette (15 min), UWM (15 min), MSOE (15 min). Walk to groceries, shop/dine at Bayshore (12 min), Fiserv (10 min), Brewers (15 min), zoo (15 min), downtown, museums, lakefront (15 min). Comfort, convenience—ideal for healthcare workers, students, business & leisure travelers!

Flat in Brookfield

Relaxing Stay Now! Pet-friendly Unit! Indoor Pool!

Guest favourite

Villa in Hales Corners

4.92 out of 5 average rating, 37 reviews

Beautiful 6 bedroom with Heated Pool & Jacuzzi

Relax with the whole family at this peaceful place to stay right in the middle of beautiful Whitnall Park. You won't find a more peaceful view of the woods and park. Our beautiful home has a large heated pool with brand new 6 person jacuzzi. Brand new Kitchen and updated bathrooms. Master suite is very romantic with steam shower, jacuzzi tub, and luxury bed and fireplace. Family Friendly OR Romantic Getaway!

Flat in Milwaukee

4.62 out of 5 average rating, 190 reviews

Downtown Studio Apartment #707

This studio offers resort-style living, right in the heart of the stylish East-Town area of downtown Milwaukee. This fabulous location is directly across the street from Metro Market! Just four blocks east to the lake and four blocks west to Water Street and only one block south to Cathedral Square park where tons of different events are held throughout the year.

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Popular amenities for Milwaukee rentals with a pool

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House rentals with a pool

Guest favourite

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 stars3 weeks ago

Excellent location and plenty of beds and bathrooms.

Guest favourite

Home in Mequon

5 out of 5 average rating, 10 reviews

Vacation home: heated inground pool on 4+ acres

AvremiRating, 5 stars1 month ago

Was a wonderful stay at the home, will definitely go back again in the summer for a nice swim in the beautiful pool! If you are looking for a little getaway in a quiet area with a home that's both comfortable and modern I highly recommend this stay!

Superhost

Home in Sussex

4.88 out of 5 average rating, 112 reviews

Wooded Hills/Indoor Pool/Hot Tub/Arcade

KaitlynRating, 5 stars2 weeks ago

Great stay. Pool could have been cleaned better before our stay.

Home in Caledonia

4.85 out of 5 average rating, 75 reviews

7 1/2 Acres! Pool! Hot Tub! Fishing Pond!

SherriRating, 5 stars2 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 favourite

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 favourite

Home in Brewer's Hill

4.97 out of 5 average rating, 176 reviews

The Peacock Place w/ Seasonal Outdoor Heated Pool

LisaRating, 5 stars5 days ago

Stephanie and Jesse were excellent hosts! They were very easy to get in touch with and, while they stay in the apartment upstairs, we never felt intruded upon. The pool is across the street, but with small kids with us, that actually was a bonus safety feature. It is very easy to get to and our hosts were easy to get in touch with when we needed help with access. The place is super cute and had everything we needed. Love the decor and vibes!

Guest favourite

Home in Riverwest

4.92 out of 5 average rating, 26 reviews

Central Location w/ Skyline View

CieraRating, 5 stars3 months ago