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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Superhost

Farm stay in Germantown

4.97 out of 5 average rating, 107 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

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

4.14 out of 5 average rating, 29 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.

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, 153 reviews

Make Yourself At Home! Close to Lake & Airport!

I want you to be able to do things here that you can't do in a hotel. If you're grillilng out, having a bonfire or watching movies all night long, you can turn up that volumn as loud as you want all night long! I posted my listing under "entire home" as you do get so much more than just renting "a room". When I have guests I stay in my office or bedroom so my guests feel more comfortable utalizing entire home & yard. In fact, if you don't ask for breakfast, you may not even see me at all.

A cozy living area is depicted, featuring a comfortable couch and a wooden coffee table amidst light green walls. A television is positioned next to a bookshelf filled with books. A dining area with black chairs and a large table is visible in the background, enhancing the inviting atmosphere.

Home in Milwaukee

4.75 out of 5 average rating, 12 reviews

Lilac Cottage

2 bedroom 1 bath house close to the airport and easy access to the freeway to go downtown. 7 minutes to airport, 9 minutes to downtown. Parking for two vehicles available in the back via alleyway access. Pets welcome, fenced in backyard This quaint house is perfect for your time in Milwaukee, wonderfully located, and perfectly comfortable. Enjoy board games or enjoy some TV with almost every streaming service available. I have 2 dogs but they will not be present during your stay.

Superhost

An outdoor pool area is shown, surrounded by a spacious deck. Umbrellas provide shade over lounge chairs, and various seating options are arranged around the pool. Lush greenery is visible in the background under a partly cloudy sky.

Home in Mequon

5 out of 5 average rating, 11 reviews

Vacation home: heated inground pool on 4+ acres

TIMELESS CHARM MEETS MODERN ELEGANCE Where the charm of classic aesthetics seamlessly intertwines with the conveniences of contemporary living. Nestled amidst the serene landscapes of Wisconsin. 4 acre + estate with plenty of room for outdoor activities such as swimming, water basketball & volleyball, outdoor basketball, sunbathing, barbecues or picnics. This vacation retreat is only minutes away from Lake Michigan, movie theaters, restaurants, golf courses, coffee shops.

Superhost

Home in Brewer's Hill

4.93 out of 5 average rating, 151 reviews

Brewers Hill Gem w/hot tub & seasonal shared pool

Your family will be close to everything when you stay at this centrally-located place. Walking distance to Brady Street, the Milwaukee River Walk, shops, restaurants and coffee houses. Less than a mile from Fiserv Forum, downtown Milwaukee and just minutes from Bradford Beach. This pet friendly unit has a private fenced in yard, BBQ grill, off street parking for your vehicles and motorcycles, and a hot tub for your use.

Superhost

Villa in Hales Corners

4.93 out of 5 average rating, 41 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 Lower East Side

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 Lower East Side

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.... 😊

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

A bright and airy living space features a soft-toned sofa and a wall-mounted TV. A small work area with a chair and desk aligns against the wall, while large windows allow natural light to fill the room, providing a sense of openness. Two additional communal areas are visible, showcasing varied seating arrangements and decorative plants.

Apartment in Lower East Side

4.91 out of 5 average rating, 32 reviews

Modern Luxe 1BR Apt NO1 with Balcony+Pool+Gym

Enjoy luxury living in this brand new building on Milwaukee's East Side. The building is fully loaded with amenities so you can live, work, and play all under one roof. And when you're ready to venture out, the central location provides quick access to Fiserv Forum, Lake Michigan, Brady St, and more.