Vacation rentals in Greendale

Designer Home in Walkable Historic Greendale

Extended Stays Welcome! Situated in an ideal walkable location, the Villager on Arrowwood is an absolute gem in the heart of the historic Village of Greendale. Updated with a modern style and mid century touches. Work from the office which includes a fold-out couch. Enjoy dual outdoor spaces with the front screened porch and large backyard with patio. Just steps from Village's inviting downtown shops and restaurants - the perfect place to experience the unique charm and history of Greendale!

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 ! 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 BOAT TOURS AVAILABLE

Cozy, historic home in walkable Greendale village

Your family will be close to everything when you stay at this centrally-located, original but renovated 3 bedroom/1.5 bath in the Historic Village of Greendale. Enjoy a stroll through the walkways connecting various parks, shopping and dining on just a few blocks away on Broad Street. You'll love the friendly village vibe. Just an easy 15 minute drive from downtown/lakefront, if you are in the mood for a city vibe. We hope you enjoy this cozy home and the village of Greendale as much as we do!

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.

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.

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!

Funky 2BR in Prime Bay View - w/ Parking

Perfectly located on the main strip of KK in MKE's eclectic Bay View directly next to restaurants and bars. Minutes from downtown, Summerfest, art museum. You’ll have the entire first floor of this sunny duplex. Stylishly designed - 2 bedrooms with Casper mattresses, a bright kitchen with seating area, record player, a work space in the master, and a comfy living room with a smart TV. The space has a small backyard area, an in-unit washer & dryer as well as 1 off-street parking space.

Wisconsin Treehouse Getaway!

Featured in Timeout Magazine as Chicago's Top 10 Airbnbs, and in other outlets as Wisconsin's most romantic and top 5 Airbnbs, this space has an immersive nature experience, overlooking a creek and woods with all modern comforts. Imagine yourself in a cabin in the woods to unplug and recharge, waking up to chirping birds as if in a Treehouse! 3 miles to Lake Michigan & dwntn. lf we're home, a complimentary Chai! Come, make lifelong memories at Racine's Best Kept Secret No local bookings.

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.

★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!

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.

Historic Hawthorne House

Nestled just steps from Grant Park Beach & Lake Michigan, the scenic Seven Bridges Trail, and the lush Grant Park Golf Course, this unique rental offers a blend of history, charm and comfort. Only a 10 minute drive to Mitchell International Airport and an easy 20 min drive to downtown Milwaukee. Whether you're here to unwind in nature, explore the local parks, enjoy a peaceful lakeside stay, or enjoy the best that Milwaukee has to offer this home has everything you need.