Vacation rentals with a pool in Milwaukee County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Milwaukee County

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.

Top guest favorite

Home in Milwaukee

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!

An indoor swimming pool area is shown, featuring a clear pool with steps leading into the water. Loungers are positioned nearby, and large windows allow natural light to enhance the space. A whirlpool is visible, with steam rising from the water's surface.

Apartment in Wauwatosa

4.22 out of 5 average rating, 27 reviews

Discover Wauwatosa! Indoor Pool, Free Parking!

The property is excellently situated downtown in Milwaukee, the heart of Wauwatosa in the beautiful state of Wisconsin. Visitors to the area should explore the charming city of Wauwatosa, with the Mayfair Collection shopping center and the Milwaukee County Zoo only 2 miles away. Visit the Harley-Davidson Museum and Miller Park, both a short drive away. Discover the historic Pabst Mansion and experience the natural beauty of the Mitchell Park Horticultural Conservatory, also known as The Domes.

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!

Guest favorite

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!

A modern living space features a light-colored carpet underfoot. A gray sofa with decorative cushions is positioned across from a sleek coffee table. A dining area is visible with a round table and upholstered chairs, while large windows allow natural light to fill the room.

Apartment in Milwaukee

North End 519

This special place is close to everything, making it easy to plan your visit. North End is a lively property where we offer fully furnished studios, stocked with everything you need to feel at home. North End is in a community that includes a Fitness Center, Lounge, and Covered Parking - Fee may apply. North End is a Walker's Paradise with a Walk Score of 92, a Transit Score of 67, and a Bike Score of 83.

A modern living room showcases a sleek sofa with decorative cushions, a glass coffee table featuring an artistic arrangement, and a large mirror reflecting natural light. Set against a neutral grey wall, a wall-mounted television and elegant wall decor contribute to the stylish ambiance.

Apartment in Milwaukee

Beautiful Downtown 2 Bedroom 2 Bathroom Apartment

Take it easy at this unique and tranquil getaway. This is a Beautiful cozy two bedroom two bedroom unit. That offer a peaceful relax environment, with a view of Downtown. There's balcony, a gym, pool and game run available for your convenience. You will be in walking distance. From the Fiserv Forum (Bucks Arena), grocery stores, restaurants and night life. You're going to Love your stay here.... 😊

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.

An aerial view reveals a vibrant green park area featuring neatly trimmed lawns and shady trees. In the foreground, a well-maintained pool glimmers, surrounded by lounge chairs. The backdrop showcases a mix of high-rise buildings, characteristic of the downtown Milwaukee skyline.

Apartment in Milwaukee

4.65 out of 5 average rating, 183 reviews

Downtown Studio Apartment #407

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 County rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favorite

Home in Milwaukee

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 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 Milwaukee

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