House holiday rentals in Greendale

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Popular amenities for Greendale house rentals

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 Lake Geneva
5 out of 5 average rating, 33 reviews

Cozy cabin getaway near Lake Como and Lake Geneva

DanielRating, 5 stars1 week ago
Sasha’s place was even better than expected. We all felt at home and it was very relaxing. We had plenty of room to accommodate all of the guests.
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!
Top Guest favourite
Home in Lake Geneva
5 out of 5 average rating, 40 reviews

Newly Updated Modern Lake Condo

LaurenRating, 5 stars4 weeks ago
Loved this house! It was in a great location, a few mins away from town, walking distance to Lake Como and super easy to find and navigate. Everyone had a great time. Only drawback was a tiny kitchen for multiple people but the rest of the living areas were great!
Guest favourite
Home in Lake Geneva
4.96 out of 5 average rating, 74 reviews

Relaxing getaway/StepsToLake/Pool/Tennis/nearDT/WD

SarahRating, 5 stars2 days ago
We had a great stay at Steven’s lake condo! The place was exactly as described and had everything we needed. Steven was a great host and provided a very helpful guide ahead of time with information about check-in, the condo, and the surrounding area. We would definitely stay here again!
Superhost
Home in Lake Geneva
5 out of 5 average rating, 6 reviews

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

ADAMRating, 5 stars2 weeks 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 stars2 weeks ago
Great stay. Pool could have been cleaned better before our stay.
Guest favourite
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. 😎

Weekly house rentals

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 stars3 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 Caledonia
5 out of 5 average rating, 16 reviews

Massive yard & basement with cinematic experience

SiddharthaRating, 5 stars3 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
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 stars5 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.
Top Guest favourite
Home in Saint Francis
5 out of 5 average rating, 13 reviews

South Shore Guesthouse

AndrewRating, 5 stars1 day ago
We had a great stay at the South Shore Guest House in St. Francis, WI. Krystyna was super responsive in her communication, gave great local recommendations for food and shops, and provided a fantastic “home base” while we explored Milwaukee and the surrounding area. The bike trails are only minutes away with several places to eat along the path. The trails are also only a short walk from her guest house and the lake is beautiful! The house is well appointed with everything you need to make a meal in the kitchen or relax on the couch watching a movie. She provided local snacks and coffee which was a nice treat. Her checkout instructions were clear as day and super easy. The place was well kept and nicely decorated. We would definitely stay again! Great host!
Guest favourite
Home in West Allis
4.9 out of 5 average rating, 60 reviews

Green Valley Homes - Updated Lower Apartment

BasheerRating, 5 stars2 weeks ago
The most important thing about me when I travel is to be in a good and safe neighborhood, it was a great neighborhood and u well find anything that you need in side the house like shampoo and towels even books and toys, my kids where so happy that my 2 years old don’t want to leave, thank you for making my first experience on Airbnb so good and clean😀
Guest favourite
Home in Waukesha
4.98 out of 5 average rating, 86 reviews

Brand New Studio w. Private Entry + Garden Patio

AdrienneRating, 5 stars2 weeks 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.
Guest favourite
Home in Milwaukee
4.87 out of 5 average rating, 87 reviews

Quiet Bay View Getaway

MichaelRating, 5 stars1 week ago
Eric was a wonderful host. The experience my girlfriend and I had was impeccable and made our time in Milwaukee one to remember. If I come back to Milwaukee, Eric is on the top of my list!

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!
Top Guest favourite
Home in West Allis
5 out of 5 average rating, 30 reviews

Spacious 4 Bedroom Bungalow

TrayvonRating, 5 stars1 week ago
I had an amazing stay at this Airbnb! The place was exactly as described—clean, cozy, and thoughtfully decorated. The bed was super comfortable, and the kitchen had everything I needed. It was in a great location too, close to local shops, restaurants, and public transport. Our host was incredibly responsive and welcoming, offering great tips about the area and making check-in and check-out a breeze. It’s clear they put a lot of effort into making guests feel at home. I would definitely stay here again and recommend it to anyone looking for a relaxing, hassle-free stay!
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!
Guest favourite
Home in Wauwatosa
4.9 out of 5 average rating, 63 reviews

Brew City Boho - Wauwatosa

KathyRating, 5 stars1 week 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.
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!
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 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, 17 reviews

Auburn Place: Cozy 3BR Home in Wauwatosa

J BlairRating, 5 stars4 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.

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