
House holiday rentals in Milwaukee
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Top-rated house rentals in Milwaukee
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Popular amenities for Milwaukee house rentals
House rentals with a pool

The Gem of Brewers Hill w/hot tub & seasonal pool
Excellent location and plenty of beds and bathrooms.

Vacation home: heated inground pool on 4+ acres
Was a wonderful stay at the home, will definitely go back again in the summer for a nice swim in the beautiful pool! If you are looking for a little getaway in a quiet area with a home that's both comfortable and modern I highly recommend this stay!

Nautical Escape •Spacious Home•Pool /Cedar Hot Tub
We loved the pool and quiet neighborhood. Check-in was easy - Matt let us know we could check in early at 1. The hot tub wasn't heating up all the way so we contacted Matt and he came over and fixed it within 10 minutes. He was very responsive and attentive. We had everything we needed and it was a nice space to have a few friends over and hang out in the pool. The hot tub was nice, very comfortable to sit in and heated up quickly. Overall we had a great experience and would visit again, for sure!

Wooded Hills/Indoor Pool/Hot Tub/Arcade
Great stay. Pool could have been cleaned better before our stay.

7 1/2 Acres! Pool! Hot Tub! Fishing Pond!
I think this was my favorite place I’ve rented. I’m glad I found it just an hour outside the suburbs of Chicago. It’s a country feel with a ton of activities as described, plus a few extra. My boys really enjoyed the game room. There’s a TV so we played music videos while playing darts, billiards, and I enjoyed throw back video games like Donkey Kong, Centipede and Dig dug. It was cooler outside so I definitely want to return in the summer to enjoy the pool, bonfire, fishing pond, but we had one nice day so still got to enjoy the large property, paddle boat, swings, bocce ball and hot tub. The house has very comfortable furniture, like the beds and couches. We watched movies at night and slept well. Robert was a great host and I appreciated all the helpful notes around the house. I almost felt guilty it was just me and my boys, but it was a perfect getaway. Plenty to do, or do nothing and enjoy the views.

Make Yourself At Home! Close to Lake & Airport!
Ann is a wonderful host. She welcomed us with slushes and said dhe could commidate early arrival and late dismissal. It was raining when we arrived and we decided on staying at the house for the evening where we enjoyed the hot tub. The next day we were greeted with a great breakfast. Ann also recommended a more private beach location to enjoy. I also enjoyed loving on her golden retriever and cats and watching the bunnies scurry around outside. We would stay again if we were in this ares.

Central Location w/ Skyline View
Cute place! Stayed here for a couple months. Dave and Cathy were very friendly and welcoming and quick to fix any issues.

Townhome Villa private oasis
Weekly house rentals

2Bdrm home next to Humboldt Park
Jean‘s House is charming—it was very clean and comfortable. Woodwork was beautiful and so many of the original features of the home have been kept in excellent condition or renovated to make it a great mixture of a vintage aesthetic with the modern comforts. You cannot do without a car if staying here. But if you have a car it’s a convenient base for doing things in Milwaukee. Great list of recommendations (At Random is a great little cocktail venue).

Entire Cozy Cottage! Pet Friendly, No Cleaning Fee
Absolutely loved our stay! The place was beautiful—clean, cozy, and stocked with all the essentials. The location was perfect, super close to the cutest local cafés and restaurants. There was even a super helpful binder with local recs and info that made getting around easy. The host was warm and welcoming from the start. I’d 10/10 recommend this spot and would definitely stay here again!

Bass & Sparrow - Spa Retreat on the MKE River
You would have no idea this place is in Milwaukee. It truly felt so secluded, like you were hours away from downtown. The hot tub, sauna, river right there…might has well been at a resort. Truly one of the most memorable weekends and we can’t wait to reserve another stay with Brad!

East Side 2nd floor Gem
Heather’s a great host and the place is large comfortable and homey. Very well equipped and good sized kitchen. Nice bathroom with big tub and good shower. It’s a bit close to a mildly busy street but traffic noise pretty minimal. There’s a Walgreens and some good casual places to eat nearby but a longer walk to Downer, Five Points, Whole Foods, sit down restaurants and the lake front (20-30 minutes and a nice walk through Murray Hill.) Easy to drive places and Heather provided off street parking. Good access to MKE River trails and neighborhood parks. Our daughter’s family lives nearby. We would come again. Note this is on 2nd floor with steps to get up and down.

The Art Loft House
Wow, just wow. This was a beautiful home! We were blown away when we arrived. The decorations and attention to detail were spot in. The location of the home was great, close to restaurants and walkable to coffee shops. Parking was perfect because we traveled with our kids. Thank you, Jenni and David. Highly recommend this home!

Auburn Place: Cozy 3BR Home in Wauwatosa
Nice property with off street parking, close to everything you want to do in Milwaukee. *Almost* walking distance to watch a Brewers game (2.5 miles). Great grocery stores and restaurants nearby - some within walking distance. Check in earlier than most properties - and check out instructions were easy and reasonable. The hosts communicate well and any questions or concerns I had were answered promptly. Tosa is a quiet, safe, family suburb. This is a good option if your plans bring you to Milwaukee.

2BR Sunny Upper in Prime Bay View - w/ Parking
We immediately felt at home & very comfortable ~ loved the decor. We even took time to spin a vinyl this morning before check out ! Did not move our car after check-in. We were able to walk to great restaurants & had easy access with Uber to the amphitheater. Great location …loved the vibe of the neighborhood! Mark’s place was pristine clean the beds and linens were amazing so comfortable!

Cozy Milwaukee cottage (whole house), sleeps 6
We were vising family who lived just a few blocks over and we were able to walk back and forth to their place a few times everyday. The neighborhood felt very safe and it was nice and quiet. We really enjoyed the outdoor sitting area and used it quite a bit to hang out outside and play cards. The stairs really are steep but seemed doable. The only concern I had was with the very small landing at the top the stairs. We had a quick group discussion to make sure everyone was careful with the are, and ended up having no problems with it.
Private house rentals

Brew City Inn with Hot Tub
Garfield Getaway was wonderful! Every little detail was carefully thought out. The beds were super comfortable. The bonus room with jacuzzi was a great area to hang out in and enjoy! The house was spotless and beautifully furnished! Pri was a stellar host! She responded to any questions we had with enthusiasm and great information! First trip to Milwaukee…..but hopefully will not be our last. A wonderful city!

Designer Home w/ Lake Views + Walk to Beachfront
What a wonderful stay! It’s was the living room and patio overlooking the lake that got us and it did not disappoint! The sleeping quarters and bathrooms were 5 star given comfort and amenities. While we did not use the garage due to the size of our vehicle, a huge plus that are driving personal vehicles. Jason and Melissa were very responsive with a few questions and guidance. While it was a homecoming for us, a definite recommendation for those that are visiting from out of town!

Cozy home
Quiet neighborhood close to all our destinations. Duplex but never ran into anyone else. Always parking available near house. Inside was peaceful and clean. Just the getaway we needed.

Whitefish Bay Beauty!
Beautiful home in a great area of town. Close to downtown but away from the hustle and bustle. The back patio area feels like an oasis and a great place to unwind after the day. The house has everything you need for a wonderful family trip and I would definitely recommend it to anyone visiting the area

The Stallis Palace
Great location for all the attractions we were interested (Milwaukee county zoo, downtown, American Family Field). Easy to find. Easy parking. One small hiccup with the AC but Michael was quick to respond to messages about the issue and quick to get the problem solved. By the time we had returned from our days activities the repairs had been made!

Brew City Boho - Wauwatosa
We really enjoyed our stay at this house. The location was great and was close to grocery stores, parks, restaurants, and attractions such as the zoo. It was also very quiet. We really appreciated the off street parking. Overall a great experience.

Festival Season- Music, food and Brady St Vibes
THANK YOU to Nina and co. For allowing my dogs and I to rent your BEAUTIFUL house! This house is in an amazing location, close to everything, and it is clean, comfortable, and cozy! I slept great every single night. The kitchen is spacious, and if you like to cook, all kitchen necessities are provided. Or if you prefer to order in food, sky is the limit! I was able to DoorDash whatever I wanted at any time of day or night. The backyard is absolute my favorite—Fenced in and secure for the dogs, but also very private. Nina and her co-hosts, Christoper & Rebecca, are TOP NOTCH! Before arrival, they explained how parking on the street worked, and were lightning fast answering all of my questions. When I **stupidly** locked myself out of the house, I was able to contact Airbnb customer service, who then relayed my situation to my hosts who were able to unlock the door for me remotely, and very quickly. Thank you again so much! I highly recommend, and would stay here again!

Relax at Muskego Lakehouse – 30 mins to Downtown!
This was our second time staying here and it was just as perfect as the first stay. So peaceful, clean and felt right at home!
Quick stats about house rentals in Milwaukee
Total rentals
1.2K properties
Total number of reviews
40K reviews
Family-friendly rentals
850 properties are a good fit for families
Pet-friendly rentals
400 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
660 properties have a dedicated workspace
Destinations to explore
- Downtown Chicago Holiday rentals
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- Six Flags Great America
- Erin Hills Golf Course
- Milwaukee Public Museum
- Alpine Valley Resort
- Kohler-Andrae State Park
- Geneva National Resort & Club
- Illinois Beach State Park
- Racine North Beach
- Bradford Beach
- Grand Geneva Resort & Spa
- Milwaukee County Zoo
- Richard Bong State Recreation Area
- Wilmot Mountain Ski Resort
- Harrington Beach State Park
- Milwaukee Country Club
- The Bull at Pinehurst Farms Golf Course
- West Bend Country Club
- Heiliger Huegel Ski Club
- Springs Water Park
- Discovery World
- The Mountain Top Ski & Adventure Center at Grand Geneva
- America's Action Territory
- Blue Mound Golf and Country Club
- Sunburst