House vacation rentals in Greendale

Find and book unique houses on Airbnb

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Popular amenities for Greendale house rentals

House rentals with a pool

Top guest favorite
Home in Delafield
4.95 out of 5 average rating, 39 reviews

Cute and cozy 2 bedroom house perfectly located!

LisaRating, 5 stars1 month ago
Our first time in Delafield and loved it!! Adorable little lake town with so many cute restaurants, coffee shop and ice cream just a short walk away. Elizabeth's home was exactly what we needed for a month long mother/daughter stay while attending treatment in the area. Meticulously clean at check-in and decorated so cute with finest attention to detail! So warm and cozy providing a perfect sanctuary. Elizabeth was flexible and responsive in all communication prior to and during our stay, and quickly addressed an Internet hiccup, ensuring the issue was resolved for us. Can't wait to return and highly recommend Elizabeth and this adorable gem of a home!!
Guest favorite
Home in Mequon
5 out of 5 average rating, 9 reviews

Vacation home: heated inground pool on 4+ acres

MandolynRating, 5 stars8 months ago
This is the perfect place to get away from it all! Clean and quiet. Surrounded by nature. A true place to relax, spend time with the family, and reset from a busy life. Thank you!!!
Guest favorite
Home in Racine
4.88 out of 5 average rating, 26 reviews

Nautical Escape •Spacious Home •Pool /Hot Tub

CarltonRating, 5 stars6 months ago
This cozy getaway was absolutely perfect for our weekend getaway!!
Guest favorite
Home in Riverwest
4.85 out of 5 average rating, 13 reviews

Big BLUE Skyline VIEW

PersephonaeRating, 5 stars3 weeks ago
Stayed for a convention, it was great having space to come back to instead of a tiny hotel room, and everything was super convenient.
Superhost
Home in Lake Geneva
5 out of 5 average rating, 5 reviews

Oasis on Oak | Private In-Ground Pool | Hot Tub

DeborahRating, 5 stars10 months ago
It was a beautiful, restful setting for our family to celebrate my wife’s birthday. Thank you for providing a great place for us to meet!
Superhost
Home in Sussex
4.87 out of 5 average rating, 107 reviews

Amazing Five Bedroom Milwaukee Vacation Home!!

TheresaRating, 5 stars1 month ago
We had a few issues with the pool and Thomas and his crew were super responsive. The house was perfect for all of us to gather together and have our own space.
Home in Caledonia
4.85 out of 5 average rating, 75 reviews

7 1/2 Acres! Pool! Hot Tub! Fishing Pond!

SherriRating, 5 stars1 month ago
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.
Home in Cudahy
4.78 out of 5 average rating, 152 reviews

Make Yourself At Home! Close to Lake & Airport!

TanyaRating, 5 stars1 month 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.

Weekly house rentals

Guest favorite
Home in Walker's Point
4.93 out of 5 average rating, 186 reviews

HGTV Renovated Home with GREAT backyard!

HaileyRating, 5 stars7 months ago
Jenni and David’s place was exactly as described, it was wonderful! Jenni was so responsive, respectful and flexible! We LOVED the location of the home, it was very walkable, we always felt safe. It was close to some great restaurants and bars that we visited. I would highly recommend staying here!
Superhost
Home in Milwaukee
4.81 out of 5 average rating, 366 reviews

Budget Guest House #1. Private & Free Parking

JanaeRating, 5 stars3 weeks ago
Overall great, Arthur was a good host. The area is a little ghetto so at night I wouldn’t walk around but overall it was good.
Guest favorite
Home in Milwaukee
4.95 out of 5 average rating, 231 reviews

Spacious house, yard & hot tub easy drive downtown

CharissaRating, 5 stars1 week ago
Paul was flexible and super easy to communicate with. Check in and out are simple. Neighborhood was a quiet cul-de-sac and close to downtown. So convenient. We were a party of 9 and had plenty of room to gather and lounge. LOVED the saltwater hot tub. So relaxing at the start and end of our days 😊
Superhost
Home in Riverwest
4.89 out of 5 average rating, 449 reviews

Turn of The Century Modern

SloanRating, 5 stars2 weeks ago
Spring’s home was beautiful and very comfortable to stay in! Private, cozy, and she provided many great recommendations for local food and attractions. The location was convenient and easy to get to & from our destinations. We had a great trip and would definitely stay again.
Top guest favorite
Home in Muskego
4.98 out of 5 average rating, 170 reviews

3 Bedroom Muskego Home

BrianRating, 5 stars1 week ago
Kathy and Tim have a wonderful place with lots of parks within a walkable distance. Tons of amenities and very helpful recommendations!
Top guest favorite
Home in Lower East Side
4.95 out of 5 average rating, 126 reviews

Large Luxury Home - Perfect for Groups - Downtown

RachelRating, 5 stars2 weeks ago
If you’re looking for a bachelorette party stay for Milwaukee (or any big group for that matter), this is it. It slept 9 of us very comfortably and everyone had plenty of bathroom space to get ready. Great location: everything we needed was a 10-min uber away. Walked to get coffee and bagels each morning. We had the best time and this Airbnb made it all possible!!
Top guest favorite
Home in Wauwatosa
4.97 out of 5 average rating, 218 reviews

Wauwatosa/Milwaukee “Inglewood Place”Best Location

CrystalRating, 5 stars1 week ago
Lovely hosts! Barbara and Fritz made us feel very welcome in their home. The personalised message was a special touch. The place was spotless and really homey, my girls loved their beds with the cuddly toys. We couldn't have asked for more as everything was so well equipped. We will definitely stay again if we are over again. Thank you!
Top guest favorite
Home in Bay View
5 out of 5 average rating, 125 reviews

Historic Brewery Tied-House in Bayview (Sleeps 12)

JulieRating, 5 stars1 week ago
We’ve stayed in LOTS of Airbnbs, but this one “takes the cake!” It was SO clean, spacious, and comfortable. Kyle was absolutely the most responsive and proactive host we’ve ever met (and yes, we got to meet him and talk a bit which was just delightful!). He really did think of everything between the treats in the refrigerator, cupboards, and coffee/tea bar and the toiletries basket. Don’t hesitate! Book the Schlitz Castle today…and tell Kyle that Julie sent you!

Private house rentals

Superhost
Home in Waukesha
4.86 out of 5 average rating, 51 reviews

Cozy 3BR Ranch Home Away From Home

ChelseaRating, 5 stars1 week ago
Zelda’s home worked perfectly for what we needed. She was quick to respond as well. Home looks like the pictures and is in a safe, peaceful neighborhood. If we ever go back to the Milwaukee area, I will look for availability here first.
Guest favorite
Home in Wauwatosa
4.96 out of 5 average rating, 103 reviews

Historic on The Avenue

DylanRating, 5 stars1 month ago
Finding a place for a big group of guys that's conveniently located near serval bars and restaurants isn't the easiest thing to do in tosa. But, thankfully, Matt's place met all of our needs. It's a super comfy and large space—perfect for a weekend get together. I would 6/5 recommend this place!
Guest favorite
Home in Wales
4.94 out of 5 average rating, 125 reviews

Charming, Updated and Historic

DavidRating, 5 stars1 month ago
Loved this place! The place is definitely unique and definitely historic. Family and I will look to book when we return to Waukesha .
Superhost
Home in Milwaukee
4.81 out of 5 average rating, 21 reviews

Cozy house near mke airport, quiet neighborhood

SaraRating, 5 stars4 months ago
Home is cozy and all amenities listed are provided. Rebeca was always available when needed, very friendly and flexible to reservation changes. Highly recommend this Airbnb.
Guest favorite
Home in Mequon
4.92 out of 5 average rating, 60 reviews

Mequon Wedding Retreat

LianeRating, 5 stars6 months ago
David met us for check in and walked through everything! Throughout the reservation process and when we left he was very responsive. It was a beautiful home!!
Guest favorite
Home in Whitefish Bay
4.94 out of 5 average rating, 17 reviews

Whitefish Bay 3Bedroom Entire House Sleeps 4

LisaRating, 5 stars5 months ago
Such a lovely place in a quiet neighborhood, yet close to great restaurants and close to city features. The host was organized and made it easy to find and be at home.
Superhost
Home in Milwaukee
4.88 out of 5 average rating, 64 reviews

❤️ Travel + Work + Holiday Refuge

MaggieRating, 5 stars3 months ago
We had a great stay during our time in town visiting family over Christmas! The home was clean and comfortable and had everything we needed during our time there. It was great having a dedicated parking spot in the back. Super clean bathroom, plenty of clean linens, nice shower. Hosts were very responsive and helpful. We would definitely stay here again next time we are in town!
Guest favorite
Home in Milwaukee
4.96 out of 5 average rating, 23 reviews

The Hadley House

ThomasRating, 5 stars1 week ago
The Hadley House is a cute little nicely renovated place on a corner lot in a nice quiet residential neighborhood with enough off-street parking for two vehicles and plenty of yard space. Was the perfect home base when in town to visit our infant grandson. Very convenient to a neighborhood grocery store, restaurants, coffee shops. Would stay again if available the next time we’re in town. Thanks Timothy!

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