
House holiday rentals in Greendale
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Top-rated house rentals in Greendale
Guests agree: these houses are highly rated for location, cleanliness and more.

The Cozy Coop | Private Upstairs Retreat | Sleep 8
Wake up to sunrise over a peaceful backyard and enjoy your morning coffee off the balcony. Evenings are perfect by the fire pit under a starry sky. Just 5 minutes from Pewaukee Lake This private upper level comes with a large fenced in yard - ideal for relaxing and spending time together. Open-concept living, kitchen, and dining area creates a warm, inviting space to gather. Sleeps up to 8 and is best suited for small families or close-knit groups who prefer a more cozy, intimate layout.
4.92 out of 5 average rating, 212 reviews
West Allis Oasis
Come stay with us at West Allis Oasis in West Allis, WI, bring your pets too! Your cozy 2-bedroom, 1-bathroom home on a quiet street in a fantastic neighborhood. Dog-friendly and perfect for families or solo travelers, enjoy easy access to I-94 and the State Fair Park just a few blocks away. Our home offers a peaceful retreat with comfortable furnishings, a fully equipped kitchen, cozy bedrooms, and large fenced in yard. Book your stay today for the perfect blend of comfort and convenience!
4.88 out of 5 average rating, 134 reviews
Entire Wauwatosa Home!
Private, Renovated Home in Wauwatosa w/ Master Bedroom Suite, Workspace, Free Parking, Full Kitchen & Fitness Area 6 guests, 4 beds, 3 bedrooms, 2 full baths In walking distance of local restaurants & bars Near Hospitals 3.6 mi to State Fair Park 4.6 mi to Fiserv Forum 6.3 mi to Miller High Life Theater 6.9 mi to Summerfest Grounds -Washer & Dryer -WIFI -Smart TV -Fitness bike & equipment -Coffee bar -Towels -Toiletries -Dishes, Dishwasher -Games -Security System -Fenced Yard
4.89 out of 5 average rating, 127 reviews
Spacious Ranch Home Oak Creek close to Airport
Chalet style ranch home is fully furnished and offers 2400 square feet of private usable space. The 3 bedrooms, living room, dining room, family room, 1 1/2 bathrooms, kitchen, and kitchen table area are all located on one floor. You will love waking up in the morning in this quiet suburban neighborhood and looking out the many windows at the park across the street. Close to the heart of Oak Creek Drexel Town Square, 4.6 miles from the airport, & 15 minutes from Downtown Milwaukee.
4.87 out of 5 average rating, 113 reviews
★Cozy Beach Themed Home★2 Beds★Spacious Parking★
Cozy and quaint two bedroom beach themed home located in the heart of West Allis. Close to public transportation and a few minutes driving to State Fair Park, Milwaukee County Zoo, Potawatomi Hotel & Casino, bars, and restaurants! Peaceful and quiet residential spot with plenty of parking on premises. Amenities include: Spacious Parking, TV with Hulu & HBO Max, WiFi, Self Check in, Fresh Sheets & Towels, Hairdryer, Fully Stocked Kitchen, Washer & Dryer, Reading Material, and much more!
4.8 out of 5 average rating, 194 reviews
Designer Cottage-Parking, Patio, & New Kitchen
LOCATION, LOCATION! • Fast Fiber Internet TIME (MIN) 5-10 McCarty Park (Water Park, Trails, B-Ball Court) STATE FAIR TOSA 10-15 Brewers, Bucks Harley, 3rd Ward Breweries, Zoo ATTN MEDICAL Near All Hospitals PRIVATE PATIO & FENCED-BACKYARD • Seating for 4 w/ table • 🐶 can roam • Safe & secure kids play • Space for games & bags SAFE PARKING • Allows 2-4 vehicles inc. trucks & boats • 100FT off street • driveway widens LAUNDRY • W&D • Pods & D-Sheets • Util. Sink • Iron+Board
4.81 out of 5 average rating, 209 reviews
Fabulous Walkers Point Mansion w/ Bar andFireplace
This stunning Walker's Point historic mansion is completely re-imagined with interior spaces that will delight you and your guests. Host a memorable get together with friends or family and relax by the bioethanol fireplace, enjoy everything the vibrant neighborhood has to offer. We have some beautiful spaces for your enjoyment, including a finished-attic hangout space, and a secret vintage-inspired lounge in the basement. Enjoy plenty of Milwaukee history in a spectacular new form!
5.0 out of 5 average rating, 172 reviews
Relax close to everything in Milwaukee
Ranch Style home in a quiet Neighborhood. You will feel at home and comfortable! The home is well maintained and very clean. In the winters you could cozy up to a nice fire upstairs and relax with a glass of wine. Downstairs is a second fireplace you have going and play a game of pool. In The summer you can enjoy the three seasons room, with looking a cup of coffee and look at the planted flower garden. Close to the Wauwatosa village down town. Even closer to Elm Grove Village.
4.93 out of 5 average rating, 120 reviews
Historic on The Avenue
Entire Home- 3 bedrooms This beautiful historic home is centrally located in the heart of Wauwatosa! Steps from the quaint village with restaurants, bars, coffee shops and boutiques! This property marries old world charm with modern amenities. Less than 15 minutes via freeway to downtown Milwaukee, the lakefront, Marquette University, less than 10 minutes to American Family Field, 5 minutes to the Milwaukee Zoo and Froedtert/Children's hospital.
4.96 out of 5 average rating, 170 reviews
The Little Gray House
The Little Gray House is better than ever! This spring we completed many upgrades inside and out - check out our photos! We've got a few small openings left this summer, maybe they work for you? Time to book for fall and winter holidays so you can get in on the best little Airbnb around! The Little Gray House has attained rave reviews from travelers around the world for its comfort, cleanliness, and convenience. Happy to have you!
5.0 out of 5 average rating, 321 reviews
Mid-Century Inspired Upper Duplex in Bay View
Step through the carpeted private entrance of this 2nd floor home, and into a mid-century interior with a modern twist. Eye-catching touches include the collection of retro radios that give it its name, stylish decor and a subway-tiled bathroom. This cozy apartment is decorated in a mid-century theme with a modern twist. It's on the second floor of a duplex. You will have your own carpeted entrance located in the back of the property.
4.95 out of 5 average rating, 262 reviews
3 Bedroom Muskego Home
Be our guest in a Country like 1,800 sq ft home nestled in a wetlands setting with a 1 car garage. Sleeps 6 in a master suite and 2 smaller bedrooms. Home has 2 full bathrooms with 2 showers. Full kitchen with a refrigerator and a dishwasher. Has a Laundry room with washer and dryer. A gas stone fireplace graces the family room. A Large deck is out back with an outdoor gas grill. Also, a 220 Volt EV charger is available for your use
4.98 out of 5 average rating, 201 reviewsPopular amenities for house rentals in Greendale
House rentals with a pool

Close to Lake with Great Ammenities & Breakfast!
4.78 out of 5 average rating, 171 reviews
Rosie’s Eastside Garden Bungalow
4.97 out of 5 average rating, 123 reviews
Brewers Hill Gem w/hot tub & seasonal shared pool
4.93 out of 5 average rating, 200 reviews
7 1/2 Acre Private Estate w/inground pool, hot tub
4.85 out of 5 average rating, 82 reviews
Private Pool/ Private Backyard Oasis!
4.92 out of 5 average rating, 53 reviews
Greendale Estate
New place to stay
Exclusive Milwaukee Home
4.94 out of 5 average rating, 53 reviews
HARLEY RIDERS WELCOME!! 30min from all dealers
Weekly house rentals

Near to all Milwaukee favorites/ Free Parking/WiFi
4.94 out of 5 average rating, 276 reviews
2BR Sunny Upper in Prime Bay View - w/ Parking
4.92 out of 5 average rating, 180 reviews
Best stay for Brewers/AmFam private home w/parking
4.98 out of 5 average rating, 249 reviews
Spacious Wauwatosa Home In Prime Location
4.98 out of 5 average rating, 221 reviews
Family friendly, Private Patio, Walkable, Quiet
4.9 out of 5 average rating, 107 reviews
Cozy, historic home in walkable Greendale village
4.95 out of 5 average rating, 40 reviews
A Showplace of Greendale History on Apple Court
5.0 out of 5 average rating, 76 reviews
Designer Home in Walkable Historic Greendale
4.7 out of 5 average rating, 91 reviewsPrivate house rentals

2Bdrm home next to Humboldt Park
4.99 out of 5 average rating, 76 reviews
Spacious 4 Bedroom Bungalow
5.0 out of 5 average rating, 54 reviews
Lake Michigan Views • Private Cedar Sauna
5.0 out of 5 average rating, 66 reviews
Cozy Dog Friendly Home Near Airport & Downtown
4.99 out of 5 average rating, 81 reviews
Cozy 2-Bedroom Apartment upper unit in west allis
4.67 out of 5 average rating, 15 reviews
Lake Michigan Romantic Getaway
4.71 out of 5 average rating, 42 reviews
House in Alverno Neighborhood
4.99 out of 5 average rating, 96 reviews
Bright & Quiet 2BR | Parking | Airport & Bay View
5.0 out of 5 average rating, 22 reviewsDestinations to explore
- Chicago Holiday rentals
- Indianapolis Holiday rentals
- Detroit Holiday rentals
- Minneapolis Holiday rentals
- Milwaukee Holiday rentals
- Traverse City Holiday rentals
- Saint Paul Holiday rentals
- Downtown Chicago Holiday rentals
- Ann Arbor Holiday rentals
- Windsor Holiday rentals
- Grand Rapids Holiday rentals
- Saugatuck Holiday rentals
- Naval Station Great Lakes
- Six Flags Great America
- Alpine Valley Resort
- Wilmot Mountain Ski Resort
- Baird Center
- Illinois Beach State Park
- American Family Field
- Milwaukee County Zoo
- Milwaukee Public Museum
- Marquette University
- Riverside Theater
- Fiserv Forum
- Bradford Beach
- Holy Hill National Shrine of Mary
- Wisconsin State Fair Park
- Pabst Mansion
- Gurnee Mills
- South Shore Park
- Lake Geneva Public Library
- Mitchell Park Horticultural Conservatory
- Discovery World
- Betty Brinn Children's Museum
- Atwater Park
- Lake Geneva Cruise Line





