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

Guest favorite
Home in Delafield
4.95 out of 5 average rating, 40 reviews

Cute and cozy 2 bedroom house perfectly located!

LisaRating, 5 stars3 months 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, 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 favorite
Home in Racine
4.89 out of 5 average rating, 27 reviews

Nautical Escape •Spacious Home•Pool /Cedar Hot Tub

EmilyRating, 5 stars1 week ago
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!
Home in Hartford
New place to stay

Dream Country Retreat - close to Erin Hills

ArpichayaRating, 5 stars2 weeks ago
Pam is lovely and always enthusiastic. She recommends many places. Whenever there is a problem, Pam always gives a quick answer. The house is very warm and lovely. I feel lucky to stay at your house. Next time, if I have a chance, I will stay at your house again.
Home in Caledonia
4.85 out of 5 average rating, 75 reviews

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

SherriRating, 5 stars2 months 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.
Guest favorite
Home in Cudahy
4.78 out of 5 average rating, 152 reviews

Make Yourself At Home! Close to Lake & Airport!

TanyaRating, 5 stars3 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 favorite
Home in Hartland
5 out of 5 average rating, 8 reviews

3/3 | 2 Fenced Acres |Pool |Hike & Beach| in Town

LindaRating, 5 stars2 weeks ago
Enjoyed our stay. Quite quaint & inviting. Temps didn’t favor a dip in the pool, although it was 80 degree water temp. We would recommend for a family that enjoys games & swimming. We would visit again if we find ourselves in that area of WI. 😎
Top guest favorite
Home in Brewer's Hill
4.97 out of 5 average rating, 176 reviews

The Peacock Place w/ Seasonal Outdoor Heated Pool

LisaRating, 5 stars5 days ago
Stephanie and Jesse were excellent hosts! They were very easy to get in touch with and, while they stay in the apartment upstairs, we never felt intruded upon. The pool is across the street, but with small kids with us, that actually was a bonus safety feature. It is very easy to get to and our hosts were easy to get in touch with when we needed help with access. The place is super cute and had everything we needed. Love the decor and vibes!

Weekly house rentals

Guest favorite
Home in Milwaukee
4.92 out of 5 average rating, 38 reviews

Cozy home

MarleeRating, 5 stars5 days ago
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.
Guest favorite
Home in West Allis
4.96 out of 5 average rating, 67 reviews

The Stallis Palace

DiannaRating, 5 stars3 days ago
We had a wonderful stay for our family of 6 and dog! Michael was super responsive and is an excellent host. Beds were heavenly and comfortable. It took us an extra couple of minutes to find the lockbox, as it wasn't next to the front door and we checked in at night, with everything dark, but once found, we had no problems at all.
Superhost
Home in Milwaukee
4.82 out of 5 average rating, 22 reviews

Cozy house near mke airport, quiet neighborhood

AdrianRating, 5 stars2 weeks ago
The property was great and Rebecca will message if anything was needed, but everything was perfect. Great by location and lots of restaurants and close to downtown
Top guest favorite
Home in Wauwatosa
5 out of 5 average rating, 18 reviews

Auburn Place: Cozy 3BR Home in Wauwatosa

J BlairRating, 5 stars1 week ago
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.
Superhost
Home in West Allis
4.64 out of 5 average rating, 44 reviews

The Bake House

JenniferRating, 5 stars1 week ago
Amazingly clean and comfortable. This house was stellar! Well stocked, beautiful home and furnishings, but the number one stand-out was the cleanliness! Thank you for a clean comfortable place to stay.
Guest favorite
Home in Milwaukee
4.88 out of 5 average rating, 73 reviews

Relax & Play: 4BR Stay w/ Hot Tub, Arcade & More

NathanRating, 5 stars2 weeks ago
A wonderful home with great accommodations!
Guest favorite
Home in Milwaukee
4.88 out of 5 average rating, 89 reviews

Quiet Bay View Getaway

MissyRating, 5 starstoday
Very cute, private, simple & comfy!! Eric’s a great host! He always responded quickly, helped us navigate our first trip to Milwaukee& Summerfest! Really comfy bed, great shower-head, kitchens very simple, no sink but was great for a very small amount of time! Just needed a bed & shower!! Well worth the money!
Top guest favorite
Home in Racine
5 out of 5 average rating, 72 reviews

Beautiful home with amazing Lake Michigan views

NickRating, 5 stars2 weeks ago
Really enjoyed the spacious location with views of the water and a well supplied kitchen (you don't see that often, all the tools ready to go and a beautiful space to cook in!) The four of us had fun and were comfortable the entire stay, great place!

Private house rentals

Top guest favorite
Home in Caledonia
5 out of 5 average rating, 17 reviews

Massive yard & basement with cinematic experience

JamieRating, 5 stars1 week ago
This place was great for our family vacation. The home is beautiful, spacious, clean, cozy, and the nearby park and playground was perfect for our kids. The hosts were flexible with us about an early check-in process working with our flight arrival times, which was a bonus. Definitely recommend this home, and would book with them again.
Guest favorite
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 favorite
Home in Glendale
4.92 out of 5 average rating, 25 reviews

Bass & Sparrow - Spa Retreat on the MKE River

CamilleRating, 5 stars3 weeks ago
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!
Top guest favorite
Home in Okauchee Lake
4.98 out of 5 average rating, 53 reviews

Cheerful, open space, and relaxing 1 bedroom home.

MarcoRating, 5 stars1 month ago
Exciting stayng in a wonderful Place. Okochee Is a stunning Little Town on the lake where you can find relax, peace and beautiful panorama. In the house of Kathy, Everything Is studied and smart. We Hope to come back to this Amazing accomodatiion. Thank you tò Kathy and Jacky .
Guest favorite
Home in Wauwatosa
4.91 out of 5 average rating, 64 reviews

Brew City Boho - Wauwatosa

KathyRating, 5 stars2 weeks ago
Tc’s house was a perfect place for us to stay while visiting family in Wauwatosa. The location was great, close to everything. The house was very clean and exactly as described. We will definitely stay there again in the future.
Guest favorite
Home in Milwaukee
4.89 out of 5 average rating, 46 reviews

Cozy home near airport

SarahRating, 5 stars2 weeks ago
Stayed here for a wedding weekend. The house was absolutely beautiful. Very clean. Quiet neighborhood. Safe and walkable. Would definitely stay again.
Top guest favorite
Home in Racine
4.98 out of 5 average rating, 41 reviews

Mid-Century Modern Dream Getaway

CatherineRating, 5 stars1 month ago
This was a beautiful house and a beautiful location. My family had a great time exploring the rooms and enjoying the views out the many windows. Lovely trees and lawn space. The design elements of the house were so fun, this felt like a house I would tour - it was cool to stay in!
Guest favorite
Home in West Allis
4.9 out of 5 average rating, 83 reviews

3 Bedroom, 2 bath home, with gazebo By stadium

SeanRating, 5 stars1 week ago
Great place, private, quiet, cozy. There was a very minor issue when we first checked in and Gail resolved it immediately, and the rest of our stay was worry free. Would absolutely stay here again.

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