Holiday rentals in Waukesha

Beautifully Restored Historic Victorian

Whether this is for a single, couple, or small group, your stay at this historic home will truly be memorable. You’ll love the MBR suite featuring a gas fireplace, whirlpool tub, and double walk-in custom tile shower. There is an additional very nice full bath/shower on the main floor. The finished lower level has two separate rooms, each with a quality double futon with bedding available for your guests. For this attractive price, the upper 4 bedrooms are locked but may be opened for more

In the Canopy (beautiful Brookfield/Milwaukee)

Relax “in the Canopy” of beautiful maples! If you’re looking for party central…this isn’t it. But if you want a comfortable place in a tree-filled neighborhood, just a few minutes from all the best Milwaukee has to offer, you’re in luck! Perfect location for quick access to the city—or to Lake Country to the west. Quiet, comfortable, safe, surrounded by beautiful gardens. We’re in a perfect launching spot to visit Summerfest, Brewers/Bucks games, or Milwaukee's western suburbs. Bring the kids!

King Bed | Near Froedtert | Tosa Village | Parking

This apartment is perfect for medical travelers, business travelers, singles, or couples looking for a clean, affordable location close to all the action. Businesses are welcome to book for their employees. This 1 bedroom apartment has everything you need to feel at home with a location second to none. You will be staying directly on State St in the village of Wauwatosa - a wonderfully walkable neighborhood with amazing bars & restaurants, shops, and great proximity to Froedtert hospital!

Beautiful Home in Waukesha

What a wonderful location with a view from the front porch and a park in your back yard. Beautiful Brazilian Tiger wood floors in dining, living, and family room. Spacious family living area has an attractive gas fireplace as it's center point that is open to kitchen area. Off the dinette the three pane patio door has private woods view and patio area. Workout equipment in rec room. Minutes from lakes and hiking paths, Old Town Waukesha boutiques, and restaurants. Quick access to I-94

Custom Home with Lake Views + Cozy Fireplace

💫This custom home is in the heart of Pewaukee! It’s equipped with a gourmet kitchen, comfy Pottery Barn furniture & stunning lake views. You’re a quick walk to the shops, restaurants, activities and the beautiful Pewaukee Lake. ⏩️Traveling with a larger group? You can also rent additional space at this home. Browse our host profile. 🏡🏡The home is part of another rental. With the layout, you will hardly hear other guests as there is minimal shared wall space and private entries.

Lakeside Pewaukee Cottage

Get ready to enjoy this cozy, completely updated cottage. The property has neighborhood lake access to Pewaukee Lake just a short 5 minute walk away. Enjoy fishing off the piers, utilizing the provided kayaks or stand up paddle boards, or enjoying the sunset over the never-ending view of the Lake. Only a 25 minute drive to downtown Milwaukee! What better way to relax after a day on the lake than sitting in the 7 person hot tub or having a small fire in the backyard.

Modern Convenient 3BR W/ 2 King beds and Hot Tub

Welcome to your Waukesha Retreat! Convenient location, welcoming clean space, relaxing backyard, and numerous amenities; this is the Airbnb for you. Here you will be minutes away from; American Family Field for your summer baseball games & concerts, downtown Milwaukee & the airport, diverse event halls, and the State Fairgrounds. Enjoy the luxury double shower and master suite as well as an outdoor private hot tub ready for guest use. Your home away from home!

Brand New Studio w. Private Entry + Garden Patio

Beautiful studio unit, sleeps 3. Professionally landscaped patio for morning coffee, or late night stargazing. Free parking, 3 miles from I94, W/D, fully stocked kitchenette, induction stove, microwave, deluxe coffee maker, toaster oven, mini refrigerator, WiFI, Smart TV, Wireless Printer,, private fenced yard, patio heater for chilly nights. Telescope experience available for stargazing. Perfect for the traveling professional, or couple.

Entire Guest Suite w/ Garage | Waukesha

Escape to this charming 3BR home in Waukesha, WI—your peaceful retreat with a fully equipped kitchen for all your cooking needs. Perfect for both short and long stays, whether you’re here for work, medical travel, or just a getaway. Enjoy flexible booking options and ask about our extended stay discounts—the longer you stay, the more you save!