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

Home in Milwaukee

5 out of 5 average rating, 5 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

Villa in Hales Corners

4.91 out of 5 average rating, 35 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!

Guest favorite

Home in Milwaukee

4.97 out of 5 average rating, 141 reviews

The Peacock Place

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.

Serviced apartment in Milwaukee

4.83 out of 5 average rating, 6 reviews

Modern 2BD in Downtown Milwaukee

Welcome to Milwaukee's vibrant east side! You'll stay in a modern building within walking distance to many top rated restaurants, bars and attractions. Inside the apartment you'll find an expanded homeware package, free in unit laundry and updated modern furnishings. Since we are a local company, we'll always be close by to help if you need anything during your stay :)

Home in Oak Creek

4.6 out of 5 average rating, 5 reviews

Corporate Housing by MGM

Please go through the listing information before booking !!! Charming 3-Bedroom Retreat in Oak Creek Welcome to your home away from home! This charming 3-bedroom, 2.5-bath house is perfect for families, or business travelers looking for a comfortable and convenient stay in Oak Creek, WI, our home offers a peaceful retreat while being close to all the amenities you need.

Rental unit 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.

Home in River Hills

4.95 out of 5 average rating, 42 reviews

Exclusive Milwaukee Home

Charming Ranch home located in Milwaukee. Set on 5 private acres with an in-ground pool, an expansive patio with a fire pit and ample parking for 4 cars. Easy access to Interstate 43. Conveniently located just 10 minutes north of downtown Milwaukee, a vibrant city with outstanding cultural venues, professional sports, and numerous global corporate headquarters.

Guest favorite

Rental unit in Milwaukee

4.91 out of 5 average rating, 11 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.