Vacation rentals in Greendale

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Top-rated vacation rentals in Greendale

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Guest favorite
A living room is presented with a gray sofa, a minimalist table, and wooden chairs. Natural light enters through large windows, accentuated by decorative curtains. A patterned area rug covers the floor, while a ceiling fan hangs above, contributing to the room's comfortable ambiance.
Apartment in West Allis
4.95 out of 5 average rating, 226 reviews

Sunny State Fair Sojourn!

Newly renovated upper unit in a 1902 Victorian home. 2 bedroom, one bath, kitchen, dining area, living room, and office space! Less than one block from Wisconsin State Fair Park, The Milwaukee Mile and local bus routes! Minutes from American Family Field, Milwaukee County Zoo, and more! Local shuttle to Summerfest and other concerts and sporting events withing walking distance! Private balcony, free parking for one car, private laundry in the unit. Owner occupied lower for over 25 years!

Guest favorite
Guesthouse in Franklin
4.81 out of 5 average rating, 32 reviews

The Crows Nest Cottage 1

Welcome to our charming 1-bedroom cottage by a serene pond. This cozy retreat features a unique basketball/pickleball court, multiple outdoor patios, and a delightful treehouse lounge area. Perfect for relaxation or active fun! Just 5 minutes away is The Rock Sports Complex, offering top-tier activities like Topgolf, minor league baseball, an umbrella bar, hiking trails,ski hills.Whether you’re seeking tranquility or adventure, our cottage provides the ideal getaway for both. washer,dryer unit

Guest favorite
An airy living space is presented, featuring two patterned armchairs and a spacious white sofa facing a large television. Natural light floods in through expansive windows, with a view of the outdoors. A dining area with a modern table and chairs is visible in the background.
Home in Franklin
4.97 out of 5 average rating, 32 reviews

Remodeled Luxury Ranch

Welcome to a home that was never meant to be “just a rental.” After living here for years, I simply couldn’t let it go; so I transformed it into a beautiful extended-stay retreat. Every detail you’ll see was hand-selected: newly remodeled spa-like bathrooms, an upgraded kitchen, custom windows/doors, & a cozy backyard fire-pit. Stylish, updated, & centrally located, this ranch offers the comfort of a home with the feel of a boutique stay. You’ll find everything designed for a memorable stay.

Top guest favorite
A paved driveway winds through a lush wooded area, bordered by greenery and tall trees. The home can be seen nestled in the distance, blending harmoniously with the natural surroundings.
Home in Muskego
4.89 out of 5 average rating, 142 reviews

Muskego Hideaway on 2 Acre Lot

Forget your worries in this beautifully updated 4 bedroom, 2 bath home on a 2 acre wooded hillside. Convenient location with easy access to the Milwaukee airport. Only a minute's drive to Little Muskego Lake and the sandy beach at Idle Isle Park. Easy drives to Alpine Valley, Lake Geneva, and The Rock Sports Complex. Only 2 minutes from I43 for easy access to Milwaukee for Brewers, Bucks, and the many festivals. Relax on the deck or patio and watch the deer and other wildlife in the backyard.

Top guest favorite
The exterior of a vintage two-story home in a sunlit setting is shown, featuring a soft yellow façade and green window trims. A white picket fence outlines a landscaped area, while mature trees provide shade along the walkway leading to the entrance.
Home in Greendale
5 out of 5 average rating, 69 reviews

A Showplace of Greendale History on Apple Court

This entire 3 bedroom home is a vintage gem in Historic Greendale, Wisconsin — and it's all yours! • NO extra charge for cleaning! • FREE on-site parking for two cars • An EASY walk to charming boutiques & eateries • Located in a National Historic Landmark district • Steeped in 1930s History with Eleanor Roosevelt design features Features stylish, functional layout as part of FDR’s 1930s New Deal. Includes high speed Internet, central air conditioning, private patio for outdoor enjoyment.

Top guest favorite
A spacious living area features a comfortable sofa with colorful throw pillows, paired with a light coffee table on a soft rug. Large windows allow natural light to fill the room, complemented by stylish curtains, while a kitchen area is seen in the background.
Apartment in Milwaukee
4.99 out of 5 average rating, 81 reviews

Stylish 3-bd place with back yard & free parking

Comfortable 3 bedroom lower unit in a duplex, with fenced in back yard and patio. Make our apartment your home-away-from-home, while visiting Milwaukee for either business or leisure. Its three bedrooms comfortably sleep six people. Fully equipped kitchen encourages in-home cooking. There is onsite laundry and two free parking spaces . We are close to hospitals, downtown with its professional buildings, shopping, restaurants and parks. Perfect home for long-term temporary work assignments.

Guest favorite
A spacious living room features a vintage-inspired green velvet sectional sofa paired with plush pillows. A glass coffee table rests on a soft area rug, with natural sunlight illuminating the room. Decorative plants and a round mirror add to the inviting atmosphere.
Apartment in Bay View
4.94 out of 5 average rating, 885 reviews

Beautiful Bay View MKE Flat - w/parking!

This is a bright, sunny apartment on the upper level of a sweet little 1870's "Polish Flat" in the heart of Bay View, one of the city's most desirable neighborhoods! We are just steps away from some of Milwaukee's best restaurants, bars, taprooms, boutiques and coffee shops. The space features an efficiency kitchenette, living room, beautiful bedroom and renovated bathroom with walk-in shower! Close to East Side, Walker’s Point, Historic Third Ward, Summerfest, Mitchell Park and the airport.

Guest favorite
A spacious living area features a blue sectional sofa and a yellow accent chair, offering an inviting seating arrangement. A brown coffee table sits on a patterned rug, while large windows allow for natural light. A desk with a chair is positioned nearby for work or leisure.
Home in West Allis
4.87 out of 5 average rating, 121 reviews

West Allis Oasis

Welcome to our 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. Relax and unwind in a tranquil environment after a day of exploring. Book your stay today for the perfect blend of comfort and convenience!

Guest favorite
A cozy living room is highlighted by a light gray sofa adorned with decorative cushions. A small blue coffee table sits in front, complemented by a candle and a framed picture. Natural light enters through a window, brightening the neutral-colored walls.
Home in West Allis
4.79 out of 5 average rating, 182 reviews

★Cozy Beach Themed Home★2 Beds★Spacious Parking★

Welcome to this cozy 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, restaurants, and more! Peaceful and quiet residential spot with plenty of parking on premises (up to 3 cars.) Amenities include: Spacious Parking, Smart TV, WiFi, Self Check in, Fresh Sheets and Towels, Shampoo & Conditioner, Soap & Hand Sanitizer, Fully Stocked Kitchen, and much more!

Guest favorite
Bungalow in West Milwaukee
4.97 out of 5 average rating, 196 reviews

Adorn Abode

Charming upper level hygge bungalow (2 unit home total). Ten minutes from anywhere. Tucked away in the quiet village of West Milwaukee. Full of natural light and curated vintage decor. Walking distance to a few restaurants and bars, as well as the American Family Field. Enjoy a cocktail on the front balcony and watch the sunset while indulging in a classic vinyl collection. Small balcony off of the kitchen to watch the sunrise and enjoy a cup of coffee. Perfect for adventuring or relaxing.

Top guest favorite
A welcoming living area features a spacious gray sectional sofa arranged around a coffee table. A textured area rug adds warmth, while large windows provide natural light. Green plants and wall accents enhance the cozy ambiance, and the open layout leads towards the kitchen.
Home in Franklin
4.98 out of 5 average rating, 56 reviews

The Rawson House

Fully renovated 3 bedroom and 2 bath home. Walking distance to the Rock sports complex. Perfect for groups looking to discover all the great activities that Franklin and Milwaukee have to offer. Walking distance to Franklin Field, the home of the Milwaukee Milkmen. Enjoy a drink at the Umbrella Bar, hit some golf balls at the brand new Luxe Golf Bays, or enjoy local restaurants. Perfect for groups attending weddings or other events at The Lodge. Also, a quick drive to downtown Milwaukee.

Guest favorite
A spacious living area features a light-colored sofa and a rustic wooden coffee table, complemented by a textured area rug. Large windows, dressed in sheer white curtains, allow natural light to fill the room, which includes a television mounted on the wall.
Home in West Allis
4.94 out of 5 average rating, 102 reviews

The Stallis Palace

Discover modern comfort in this 3BR, 1.5BA gem in central West Allis, WI. Spacious and fully furnished, enjoy craftsman woodwork, modern decór, and an abundance of light flooding through oversize windows. Walk to shops, dining, and nightlife. Within 5 miles of several major regional medicals centers! Master BR with office, porch, and outdoor dining area. Local, experienced hosts, ultra high-speed internet, and smart TVs make this the perfect blend of style and convenience. Book today!

Popular amenities for Greendale vacation rentals

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