House holiday rentals in Milwaukee

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Popular amenities for house rentals in Milwaukee

House rentals with a pool

Superhost
Home in Sussex
4.88 out of 5 average rating, 112 reviews

Wooded Hills/Indoor Pool/Hot Tub/Arcade

KaitlynRating, 5 stars1 week ago
Great stay. Pool could have been cleaned better before our stay.
Guest favourite
Home in Brewer's Hill
4.92 out of 5 average rating, 140 reviews

The Gem of Brewers Hill w/hot tub & seasonal pool

GerryRating, 5 stars2 weeks ago
Excellent location and plenty of beds and bathrooms.
Guest favourite
Home in Mequon
5 out of 5 average rating, 10 reviews

Vacation home: heated inground pool on 4+ acres

AvremiRating, 5 stars1 month ago
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!
Guest favourite
Home in Cudahy
4.78 out of 5 average rating, 152 reviews

Make Yourself At Home! Close to Lake & Airport!

TanyaRating, 5 stars2 months ago
Ann went above and beyond to be a fantastic host!!! Her listing gives a very accurate overview of the living space and what to expect during this airbnb experience. She makes you feel at home and like you're staying at a friend or family member's house vs. an impersonal hotel. Her wonderful pets are an added bonus. There was a furry welcoming committee there to meet us at the door and to offer snuggles :) I would recommend this airbnb to anyone! It's in a peaceful neighborhood and only a short drive to shopping centers and restaurants galore.
Guest favourite
Home in Riverwest
4.87 out of 5 average rating, 15 reviews

Big BLUE Skyline VIEW

RobertRating, 5 stars2 weeks ago
Great neighborhood! loved this place. Great restaurants nearby. close to public transportation. thanks for letting us stay in your place!
Home in Milwaukee

Townhome Villa private oasis

Home in Sussex

HARLEY RIDERS WELCOME!! 30min from all dealers

Weekly house rentals

Guest favourite
Home in Brewer's Hill
4.93 out of 5 average rating, 71 reviews

Brew City Inn with Hot Tub

ReneeRating, 5 stars2 days ago
Pri was a lovely host. We had 7 girls there celebrating a bachelorette party and didn’t have any issues! The place is renovated nicely and was perfect for our group! The hot tub hangout area in the garage was so nice; we enjoyed it both nights!
Guest favourite
Home in Milwaukee
4.92 out of 5 average rating, 37 reviews

Cozy home

AndrewRating, 5 stars2 weeks ago
Jeff's house was a great spot to stay for a short little memorial day vacation for my partner and I. The house was clean and very nice. The location was very convenient for getting to and from the city. We would both stay here again and recommend this house for a milwaukee trip.
Top guest favourite
Home in Shorewood
4.99 out of 5 average rating, 96 reviews

The Menlo Guesthouse

LauraRating, 5 stars3 weeks ago
My husband and I stayed here for a very short kid-free birthday vacay and LOVED it. We used to live in Milwaukee and Savannah’s decor choices brought us right back to being in our happy place, a craftsman style home in Shorewood. Everything was spotless, fresh, clean, well stocked and comfortable. We will definitely plan to stay here if we ever get a kid-free weekend again :)
Guest favourite
Home in West Allis
4.95 out of 5 average rating, 63 reviews

The Stallis Palace

BrettRating, 5 stars2 days ago
We had a great stay! This home fit our needs perfectly—two couples with toddlers and an infant visiting the Milwaukee area for a weekend. The location was ideal, centrally positioned between the children’s museum, zoo, and Brewers stadium, and more affordable than staying downtown. The bedrooms were spacious enough for pack n plays, and the main level had plenty of space for the kids to play. Parking was super convenient with space for two SUVs on the concrete slab off the alley. The host provided clear instructions and was easy to communicate with. The only minor downside was the creaky upstairs floors, which is to be expected in an older home—just something for parents of light-sleeping little ones to keep in mind. That said, it wouldn’t stop us from staying again. Highly recommend!
Guest favourite
Home in Wauwatosa
4.9 out of 5 average rating, 62 reviews

Brew City Boho - Wauwatosa

GinaRating, 5 stars1 month ago
I really enjoyed my stay here - friendly neighbors and very walkable to all that the village of Tosa has to offer! TC was responsive to questions and helpful with recommendations. Would definitely return - thank you so much!
Guest favourite
Home in Walker's Point
5 out of 5 average rating, 28 reviews

The Art Loft House

Anh ThuRating, 5 stars2 weeks ago
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!
Top guest favourite
Home in Martin Drive
4.94 out of 5 average rating, 31 reviews

Chic lower flat near AMFAM + Davidson Park

AnthonyRating, 5 stars8 months ago
We had a very pleasant stay in this safe and family-friendly neighborhood. The house was clean and comfortable and the parking was easy. Hosts were friendly and responsive. Would definitely return when in the area!
Top guest favourite
Home in Walker's Point
5 out of 5 average rating, 59 reviews

Barclay House in Walker's Point

KristenRating, 5 stars2 weeks ago
We are so happy we stumbled upon Robert & Laura’s place for the weekend! Robert & Laura were great hosts and very responsive. The house was decorated beautifully and very clean! We will definitely keep this place in mind when we visit Milwaukee again.

Private house rentals

Superhost
Home in Bay View
4.9 out of 5 average rating, 10 reviews

Sunrise Over The Lake- Located on Desirable St

MeganRating, 5 stars2 months ago
Our family experienced a home fire on Friday. The only complaint I have is we can’t stay here until we’re back in our home! Truly beautiful, excellent location, fantastic hosts. Don’t miss on an opportunity to stay here!
Guest favourite
Home in Bay View
4.97 out of 5 average rating, 36 reviews

2Bdrm home next to Humboldt Park

AnnaRating, 5 stars2 months ago
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).
Guest favourite
Home in Wauwatosa
4.89 out of 5 average rating, 91 reviews

Entire Wauwatosa Home!

ClaudiaRating, 5 stars1 month ago
Great location, walkable to restaurants. Short distance to baseball stadium. Very comfortable accommodations.
Top guest favourite
Home in Saint Francis
5 out of 5 average rating, 12 reviews

South Shore Guesthouse

CraigRating, 5 stars2 days ago
Where do I begin...Everything was absolutely perfect! Kristyna has her home set up like a 5-star hotel! She provided anything & everything a person could need or want. She made us feel very welcomed, from the beautiful set up of the home to the extras that she provided, including fresh flowers on the extra large island in the kitchen. We loved everything about this home! Thank you Krystyna!
Top guest favourite
Home in Waukesha
4.93 out of 5 average rating, 40 reviews

Beautiful Home in Waukesha

SusanRating, 5 stars1 week ago
Much cozier than a few hotel rooms for our event. Kitchen is well outfitted, and living room has plenty of seating. Nice quiet neighborhood.
Top guest favourite
Home in Riverside Park
5 out of 5 average rating, 11 reviews

East Side Duplex-Cozy Lower Unit

TinaRating, 5 stars1 month ago
Had a great weekend stay in Milwaukee! Came to town because my son ran the half marathon and we had a great time! Jarrid's place was super convenient and perfect for where we wanted to be. Clean, homey, and made out of towners feel super comfortable! Thanks for the bottle of wine, Jarrid!!
Guest favourite
Home in Waukesha
4.98 out of 5 average rating, 86 reviews

Brand New Studio w. Private Entry + Garden Patio

AdrienneRating, 5 stars1 week ago
Hubby and I stayed Friday and Saturday night. The room was perfect for us. Not too big and not too small. Plenty of amenities in the room to make us feel welcome. We didn't get a chance to sit out on in the backyard, but the view was beautiful.
Superhost
Home in Bay View
4.95 out of 5 average rating, 38 reviews

Pet Friendly! Entire 2 Bed Home!

RachelRating, 5 stars1 month ago
We loved Caylee's place for our girl's weekend! The property style and decor are so unique and charming and added such fun energy to our stay. We appreciated the provided games and loved the location. Everything in Bayview was so close and also very easy to access downtown Milwaukee. We were able to have a small fire in the yard one night, which we really enjoyed. I Highly recommend Caylee's place, and I would stay again!

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

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  4. Milwaukee County
  5. Milwaukee
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