Some info has been automatically translated. Show original language

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.

%{current} / %{total}1 / 1
The lobby features a spacious seating area with beige lounge chairs and a purple ottoman. A colorful art installation hangs from the ceiling, and two computers are available for guest use in a bright corner. Natural light filters in, creating an open atmosphere.
Apartment in Wauwatosa
3.75 out of 5 average rating, 4 reviews

You Found it! 2 Relaxing Units, 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.

Apartment in Wauwatosa
4.26 out of 5 average rating, 34 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.

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, 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.

Guest favorite
A cozy living room features a light-colored sectional sofa complemented by colorful throw pillows. A plush, vibrant area rug adds warmth to the space. Two windows with light-filtering shades allow natural light, while a recliner and wooden table provide additional seating and surface space.
Home in Riverwest
4.89 out of 5 average rating, 18 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
A spacious outdoor patio surrounds the inviting swimming pool, featuring lounge chairs, umbrellas, and shaded seating areas. Lush greenery and trees frame the scene, enhancing the tranquil atmosphere. The bright blue sky is dotted with clouds, offering a relaxing space for sunbathing or gathering.
Home in Mequon
5 out of 5 average rating, 13 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
Apartment in West Allis
New place to stay

Cozy Modern Apartment Close to downtown/ Gym/ Pool

Welcome to your stylish and peaceful home away from home. This modern apartment features a bright open layout with warm neutral tones and elegant décor. Enjoy a fully equipped kitchen, a cozy living area perfect for relaxing, and a spacious bedroom with a comfortable bed and soft linens. Every detail has been curated for comfort — Whether you’re here for business or leisure, this space offers everything you need for a relaxing and refreshing stay just minutes from downtown.

Apartment in Milwaukee
New place to stay

Keefe Avenue-Upscale Queen Bedroom/Full Office

Unwind at Keefe Avenue, our fully equipped 1 queen bedroom and full office apartment located in North West Milwaukee's Grasslyn Manor neighborhood. The unit features a renovated kitchen & bathroom with modern transitional decor. Convenient quick access to all Milwaukee attractions, only 5 minutes from St. Joseph's Hosptial & 12 minutes to Frodert/Children's Hospital. It is 12 minutes to Milwaukee's downtown district & 15 minutes from Lake Michigan!

Superhost
Apartment in West Allis
4.75 out of 5 average rating, 20 reviews

Modern Apartment/ 8mins Downtown/ Parking/Pool/Gym

✨ Modern & Cozy Stay in the Heart of West Allis ✨ Stylish, light-filled apartment just steps away from the State Fair Grounds! Enjoy a cozy living room, fully equipped kitchen, peaceful bedroom, and access to a pool & lounge areas. Perfectly located near dining, shopping, and entertainment — right in the heart of West Allis, only steps away from the State Fair Grounds. 10 mins to Downtown Milwaukee 7 mins away to American Family Field

Guest favorite
A historic Victorian-style home is showcased with a blue exterior and ornate architectural details. Bright green foliage frames the entrance, leading to the front steps. The sky is clear, enhancing the home's inviting appearance.
Home in Brewer's Hill
4.93 out of 5 average rating, 168 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.

Guest favorite
The exterior of a mid-century modern tri-level home is showcased amidst a spacious green yard. Surrounding trees provide shade, contributing to the peaceful ambiance of the property. A large driveway is visible, accommodating multiple vehicles.
Villa in Hales Corners
4.93 out of 5 average rating, 45 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.... 😊

Popular amenities for Milwaukee rentals with a pool

When is the best time to visit Milwaukee?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$26,349 GYDG$28,650 GYDG$25,931 GYDG$31,368 GYDG$31,368 GYDG$34,505 GYDG$34,505 GYDG$34,714 GYDG$29,904 GYDG$27,395 GYDG$31,368 GYDG$25,931 GYD
Avg. temp-4°C-3°C3°C8°C14°C20°C23°C22°C18°C12°C5°C-1°C

Quick stats about vacation rentals with a pool in Milwaukee

  • Total vacation rentals

    Explore 40 vacation rentals in Milwaukee

  • Nightly prices starting at

    Milwaukee vacation rentals start at G$2,091 GYD per night before taxes and fees

  • Verified guest reviews

    Over 640 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Milwaukee vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Milwaukee rentals

  • Nearby attractions

    Milwaukee's top spots, include Milwaukee County Zoo, Harley-Davidson Museum, and Milwaukee Art Museum

Destinations to explore