Holiday 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

Farm stay

4.97 out of 5 average rating, 97 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

Home

5 out of 5 average rating, 3 reviews

Street Sign Stay - fenced yard & 5 mins to Airport

Here's your sign to book! Street Sign Stay is a cozy home located ONLY 2 miles away from MKE's General Mitchell Airport. Enjoy unique decor featuring vintage road signs that have been collected (legally) from all parts of the USA for over 30 years. Perfect for travelers seeking a comfortable and memorable stay. You are LESS THAN 15 minutes away from major attractions: 10 mins to Fiserv Forum 11 mins to Summerfest 12 mins to Am Fam Field 13 mins to 7 Bridges Hiking Trail We are pet friendly!

Home

5 out of 5 average rating, 8 reviews

Vacation home: heated inground pool on 4+ acres

TIMELESS CHARM MEETS MODERN ELEGANCE Who says summer is over on Labor Day!! Pool will be heated to 80 at no extra charge (September only) higher temp up to 90 available for extra fee. Come enjoy the fun of summer at BIG SAVINGS!!! 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

4.76 out of 5 average rating, 141 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.

Rental unit

New place to stay

2B Apartment in Downtown Milwaukee

Cozy 2B apartment . Vibrant neighborhood. With quick access to Brady St, Walter St, entertainment venues ( 5 minute drive to Fiserv Forum) and Milwaukee's prime nightlife . This home is literally steps away from the Milwaukee River . Right in the heart of the city just a few steps away from Milwaukees famous brewery , coffee shops , trendy bars , museums , restaurants, jazz clubs & more. From this prime location, exploring Milwaukee and the surrounding regions is easy and convenient.

Guest favourite

Home

5 out of 5 average rating, 9 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

Home

4.73 out of 5 average rating, 66 reviews

Paradise In Germantown! Swim 365 days indoor pool.

Are you ready for a Wisconsin getaway? Enjoy an enormous indoor swimming pool and fully-stocked house, impeccably decorated rooms, and more ensure that your stay here will be memorable and exquisite! This 2,500 sq ft beautiful home has 5 bedrooms and 2.5 bathrooms! It is in a perfect location in Germantown, WI just 5 minutes off the highway and 15 minutes from Milwaukee. This beautiful space has peaceful vibes, thoughtfully designed for you to have a relaxing and enjoyable stay.

Superhost

Home

4.87 out of 5 average rating, 102 reviews

Amazing Five Bedroom Milwaukee Vacation Home!!

Treat your friends and family to this five-bedroom vacation home just a half-hour from downtown Milwaukee on more than one acre of park-like, private surroundings. Guests of all ages will love the decked-out game room, the huge indoor pool and the comfy living space, with lots of room to spread out. Plus, you’re just 30 minutes from downtown. It’s all the peaceful feels of a country setting with the amenities of the city (think Uber, UberEats, and more).

Guest favourite

Home

4.97 out of 5 average rating, 145 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.

Rental unit

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.