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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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.

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

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!

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

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

A spacious guestroom features two queen beds with soft white linens. A wooden desk with an ergonomic chair and a large flat-screen TV are positioned against the wall. Natural light enters through a curtain-covered window, complementing the subtle patterned wallpaper.

Apartment 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.

A spacious living room features a patterned area rug that complements the dark leather sofa. A modern chair is positioned near a window, dressed with vertical blinds that allow natural light. A television is mounted on the wall opposite the seating, enhancing the room's overall comfort.

Apartment 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!

A spacious hotel room is presented, featuring a comfortable seating area with a light-colored sofa and an ottoman. A wooden desk with an ergonomic chair is positioned next to a large flat-screen TV. Soft natural light filters through sheer curtains, enhancing the neutral color palette.

Apartment in Brookfield

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

A well-maintained outdoor pool area is surrounded by landscaping and seating. A tall residential building rises in the background against a clear blue sky, showcasing a mix of windows and balconies, adding to the vibrant atmosphere.

Apartment 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.

The exterior of the two-story townhouse is visible, featuring a beige facade with dark brown trim. Large windows allow for natural light, while a patio area is accessible through a glass door. Lush greenery surrounds the property, adding a tranquil feel to the entrance.

Townhouse in Milwaukee

4.67 out of 5 average rating, 3 reviews

2 Story - 2Br Condo

Forget your worries in this spacious and serene space. 2 story townhouse story 2 Bedroom 1.5 bathroom condo with a patio and pool and courtyard for a simple stay. Perfect for in town family visits or quick work stays. The pool is open in the summer months which should be upcoming. Smoking area outside on patio or in vestibule. NO SMOKING IN HOUSE

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Popular amenities for Milwaukee rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

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

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.

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

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