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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Guest favourite

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.

Apartment in Brookfield

Minutes from Endicott Park! 2 Spacious Units, Pool

The property is conveniently situated on the outskirts of Brookfield, far from the hustle and bustle of the city. Put the Milwaukee Public Museum and Harley-Davidson Museum on your to-do list. With the New Berlin Hills Golf Course and Moorland Road Golf Center nearby, golf should also be on your itinerary. Skating is another option, as you can test your skills at the Pettit National Ice Center. Explore the beautiful parks and hiking and biking trails nearby for a reinvigorating experience.

Apartment in Brookfield

Relaxing Stay Now! Pet-friendly Unit! Indoor Pool!

Guest favourite

Home in Riverwest

4.92 out of 5 average rating, 26 reviews

Central Location w/ Skyline View

Central location for walking the city with a skyline view. Explore all of Milwaukee's most popular neighborhoods from here. Fenced in yard for your pup to run around and play. Gated area for motorcycle parking and a large patio area with basketball hoop. 1 bedroom with full kitchen and large living room with 2 dedicated workspaces with desks. Basement with free laundry facilities and an old foosball table. Queen size bed in the bedroom plus a pull out full size bed and a futon.

Guest favourite

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 Sussex

4.88 out of 5 average rating, 113 reviews

Wooded Hills/Indoor Pool/Hot Tub/Arcade

Discover the allure of our 5BR Wisconsin retreat, where spacious elegance meets comfort. Enjoy a gourmet kitchen, a grand living room, and a game room with free arcade play. Dive into relaxation with our private, heated indoor pool. Outdoors, the terraced patio and fire pit invite memorable moments. Minutes from Milwaukee, our home is an idyllic base for both peaceful relaxation and lively exploration. Perfect for family or corporate escapes, it's a stay you'll cherish.

Apartment in Lower East Side

New place to stay

Heart of the city, by Brady St downtown MKE.

Experience the best of Milwaukee right outside your door in this modern, stylish apartment nestled in the heart of Water Street. Whether you’re here for a night out, a business trip, or just to explore the city, this space offers the perfect blend of comfort, convenience, and city vibes. Whether you’re sipping coffee while bird-watching or heading out for the night, this apartment puts you in the heart of the action but with the peace and privacy to recharge.

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.

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.... 😊

Top guest favourite

Home in Brewer's Hill

4.97 out of 5 average rating, 184 reviews

The Peacock Place w/ Shared Seasonal Outdoor 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.

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.

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