House holiday rentals in Greendale

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Popular amenities for house rentals in Greendale

House rentals with a pool

Top guest favourite
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 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 Racine
4.89 out of 5 average rating, 27 reviews

Nautical Escape •Spacious Home•Pool /Cedar Hot Tub

EmilyRating, 5 stars6 days 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!
Superhost
Home in Lake Geneva
5 out of 5 average rating, 6 reviews

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

ADAMRating, 5 stars1 week ago
House was great and matches the description and photos. House is spacious, good for a group of 6-7 people and private from other neighbors. It’s also less than 10 minutes from downtown Lake Geneva. It is an ideal house if you are looking for a quiet weekend retreat, close to the areas activities. In addition, the host is responsive and helpful. Looking forward to our next stay with you all!
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.
Home in Hartford
New place to stay

Dream Country Retreat - close to Erin Hills

ArpichayaRating, 5 stars1 week 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 favourite
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.

Weekly house rentals

Top guest favourite
Home in Caledonia
5 out of 5 average rating, 15 reviews

Massive yard & basement with cinematic experience

SiddharthaRating, 5 stars2 weeks ago
We had a fantastic stay at this beautiful property over the Memorial Day weekend! The home was exactly as described—spacious, clean, and thoughtfully stocked with everything we needed for a comfortable and relaxing getaway. The peaceful surroundings were ideal for quality time with our group of friends and family, including kids. A special shoutout to Jose, who coordinated the entire visit and stayed in constant touch with us—checking in, offering help, and making sure everything was going smoothly. His support truly made our stay stress-free and enjoyable. David and Amber were wonderful hosts as well—responsive, thoughtful, and welcoming throughout. We would absolutely recommend this place to anyone looking for a serene, well-managed escape. Already looking forward to returning! — Sid & Family/Friends Group
Top guest favourite
Home in Bluemound Heights
5 out of 5 average rating, 73 reviews

Entire Cozy Cottage! Pet Friendly, No Cleaning Fee

KateRating, 5 stars5 days ago
Amanda and Troy’s place was a great little bungalow for our first trip to Milwaukee. It was quick and easy to get to the highway, yet far enough to be situated it a quiet little neighborhood. Amanda and Troy really thought of everything! We took their recommendation and enjoyed walking to Blue’s Egg Cafe & Bakery. Would recommend their place for your next trip!
Top guest favourite
Home in Saint Francis
5 out of 5 average rating, 12 reviews

South Shore Guesthouse

CraigRating, 5 stars6 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 Wauwatosa
5 out of 5 average rating, 16 reviews

Auburn Place: Cozy 3BR Home in Wauwatosa

J BlairRating, 5 stars2 days 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.
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 West Allis
4.64 out of 5 average rating, 44 reviews

The Bake House

JenniferRating, 5 stars1 day 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.
Superhost
Home in Muskego
5 out of 5 average rating, 3 reviews

Relax at Muskego Lakehouse – 30 mins to Downtown!

MariaRating, 5 stars9 months ago
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!

Private house rentals

Superhost
Home in Waukesha
4.88 out of 5 average rating, 56 reviews

Cozy 3BR Ranch Home Away From Home

KylaRating, 5 stars1 week ago
Super clean and comfortable airbnb. Stayed with 4 adults and two infants. Back yard was nice!
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 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 Racine
4.97 out of 5 average rating, 79 reviews

Farm House Retreat w/ Private Backyard & Garage

MattRating, 5 stars2 weeks ago
We were very happy with our stay. The accommodations met expectations and the host was very responsive. If we needed to be back in this area, we would stay here again. Thank you!
Top guest favourite
Home in West Allis
4.97 out of 5 average rating, 58 reviews

Fully Updated Home w/ Garage

SondraRating, 5 stars1 week ago
Emily's home was the perfect place for my visit to Milwaukee and is more beautiful than the pictures show. We were able to prepare meals for the many family members that stopped by and enjoy family game night with the various games that were provided. We even grilled and enjoyed the backyard where there's a gazebo, dining table and sofa set. The 2nd floor is like a loft apartment with an amazing shower and huge walkin closet that's big enough to be a bedroom! My teenage guests took over that space for video games but it also allowed me a private space to unwind. The king size bed and memory foam pillows were super comfy! The sound machines in each bedroom were a nice touch. I visit several times a year and will definitely stay again! Thanks Emily!
Top guest favourite
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 favourite
Home in West Allis
4.9 out of 5 average rating, 83 reviews

3 Bedroom, 2 bath home, with gazebo By stadium

SeanRating, 5 stars3 days 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.
Guest favourite
Home in Story Hill
4.89 out of 5 average rating, 64 reviews

Family friendly, Private Patio, Walkable, Quiet

HeidiRating, 5 stars4 weeks ago
Had a wonderful stay! Lovely downstairs suite for my kids and their baby, the rest of us were upstairs in the 3 comfy bedrooms. Super clean. Comfy beds. Nice gathering spaces. Highly recommend!

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