Vacation rentals with a pool in Milwaukee County

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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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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!

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.

Guest favorite

An above-ground pool is situated in a spacious backyard, surrounded by a wooden fence. Several lounge chairs and a pink inflatable float are visible nearby. A warning sign indicates swimming restrictions. A gas grill is positioned beside the pool area, enhancing outdoor leisure options.

Home in Milwaukee

4.85 out of 5 average rating, 13 reviews

Big BLUE Skyline VIEW

This bright and roomy 2 bedroom unit is the lower level of a 1900 Victorian duplex in the heart of Milwaukee was renovated 3 years ago. Situated on the edge of downtown, overlooking the river and downtown skyline you’ll have easy walking access to all the best neighborhoods. With 9 foot ceilings and a big fenced in yard with basketball hoop and patio furniture you'll be very comfortable staying with us. We are not a corporation, just a nice couple sharing our place. FREE PARKING too

Guest favorite

Home in Milwaukee

4.93 out of 5 average rating, 134 reviews

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

Guest favorite

Villa in Hales Corners

4.92 out of 5 average rating, 36 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!

Top guest favorite

Home in Milwaukee

4.97 out of 5 average rating, 166 reviews

The Peacock Place w/ Seasonal Outdoor Heated Pool

This 3 bedroom, 1 bath, open concept lower unit of a duplex is located in Brewer's Hill. This unit has tons of natural light, original hard wood floors, pocket doors and claw foot soaking tub. This pet friendly unit has off street parking for 2 vehicles or motorcycles, and a private yard with patio and BBQ grill for your use. Walking distance to Brady Street, downtown and Fiserv Forum.

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

A comfortable living area features a large coffee table at its center, surrounded by a variety of seating options, including two patterned sofas and two armchairs. Bright artwork adorns the walls, and large windows provide natural light and a view of the outdoors.

Apartment in Milwaukee

4.65 out of 5 average rating, 136 reviews

Downtown One Bedroom Apartment #305

Featuring one queen size bed and a large L-shaped sofa, this apartment offers resort-style living, right in the heart of the stylish East-Town area of downtown Milwaukee. 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

New place to stay

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

Apartment in Milwaukee

4.89 out of 5 average rating, 19 reviews

Flexhome East Side 1BR NO1 - 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.