Vacation rentals in Waukesha

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Top-rated vacation rentals in Waukesha

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favourite
The living area features a spacious light-colored sectional sofa paired with a warm leather armchair. A cozy gas fireplace is framed by a stone wall, and large French doors allow natural light to fill the space while providing access to the outdoor area.
Home in Pewaukee
5 out of 5 average rating, 18 reviews

Custom Home w/ Lake Views & Cozy Fireplace

💫Custom home centrally located in Pewaukee! It’s equipped with a gourmet kitchen, comfy Pottery Barn furniture, gas fireplace & stunning lake views. 📍You’re a quick walk to the shops, restaurants, activities and the beautiful Pewaukee Lake. 🏡🏡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. ⏩️Traveling with a larger group? You can also rent additional space at this home. Browse our host profile.

Top guest favourite
The exterior of a charming house is showcased, featuring a welcoming front porch adorned with string lights. Lush greenery surrounds the home, with a flower garden displaying purple blooms. A pathway leads to the entrance, enhancing the inviting atmosphere of the property.
Home in Menomonee Falls
4.95 out of 5 average rating, 169 reviews

Exhale, rest

Exhale. The perfect combination. This home is right in the village of Menomonee Falls with great shopping and restaurants within walking distance. Close to the highway, it’s also a mere half an hour to anything Milwaukee so games, museums, festivals are all also at your fingertips. At the end of dead end road with views of the river, access to trails, and a secluded deck and fire pit, there is definitely also a rural feel. This location has it all. Go out, live life, come back, exhale and rest.

Top guest favourite
A historic home features a multi-gabled roof and intricate architectural details. The exterior showcases a blend of light and dark hues, complemented by well-maintained landscaping and a spacious lawn. A charming porch wraps around the front, providing an inviting entrance with rocking chairs nestled on one side.
Home in Wales
4.94 out of 5 average rating, 194 reviews

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

Top guest favourite
A two-story house is surrounded by a snow-blanketed yard, with tall trees silhouetted against a twilight sky of vibrant pinks and purples. The warm glow of lights from the front windows contrasts with the cool tones of the winter scenery.
Guest suite in Brookfield
5 out of 5 average rating, 256 reviews

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!

Guest favourite
A bright living area showcases a comfortable seating arrangement with decorative cushions. Potted plants add greenery, and light streams in through the large windows. Artwork adorns the walls, while a mix of textures is provided by the rugs and furnishings.
Apartment in Bay View
4.94 out of 5 average rating, 381 reviews

Bay View MKE Hideaway - with Parking!

Cozy, inviting, one bedroom apartment in the heart of Bayview, literally steps away from some of Milwaukee's best restaurants, bars and shops! One of two Airbnb guest spaces in our house, this downstairs apartment is our home base when we're in Milwaukee, and we love sharing it with guests when we’re on the road! We are within five minutes of Summerfest grounds and East Side & Historic Third Ward districts, and within 10 minutes of the airport, downtown, Marquette University, and Miller Park.

Superhost
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
4.84 out of 5 average rating, 102 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!

Top guest favourite
A spacious outdoor deck is featured, overlooking a lush green backyard. Visible are various plants and garden elements, along with a patio umbrella. Stairs lead down from the deck to the garden area, providing access to the vibrant surroundings.
Guest suite in Waukesha
4.97 out of 5 average rating, 59 reviews

Tucked Away

For those in need of a "home away from home" while on the road working or just passing though on your travels. This private, quaint backyard parking/entrance mini apartment located in Waukesha's "Historic District" is for you. Enjoy large outer deck as weather permits. Stairs are required outside to enter unit. Walking distance to downtown area. Easy access from this location to Madison (65 miles) and Milwaukee (12 miles). Located near Carroll University and Waukesha Memorial Hospital

Top guest favourite
A cozy living area features a soft sofa adorned with colorful cushions, complemented by an accent chair. A stylish glass coffee table sits atop a geometric-patterned rug. Natural light filters through two windows, enhancing the warm ambiance of the space.
Townhouse in Bay View
4.95 out of 5 average rating, 451 reviews

Vintage Bay View - Big Backyard, Big 1 Bedroom

Welcome to your Milwaukee getaway! Located in the Bay View area, you're walking distance from the best farm-to-table restaurants, music venues, art fairs, and craft beer in the city. Not only that, but Lake Michigan's beaches, Miller Park, and downtown are a short drive away. The location is ideal. The place was created with a 70's midwestern feel, with wood-paneled furniture pieces and mod design. It also boasts a giant kitchen and backyard with grill. We can't wait for you to visit!

Top guest favourite
A historic stone home is presented, featuring multiple windows that enhance its classic appeal. A well-maintained garden with colorful flowers surrounds the exterior, creating a welcoming entrance to the Butler Place. A sign displaying the property's name is held by two guests in front of the house.
Guest suite in Sussex
4.96 out of 5 average rating, 319 reviews

The Loft @ The Butler Place. 1846 homestead.

The Loft at the Butler Place is a beautiful, quiet retreat set in the rural suburb of Sussex, just 30 minutes west of Milwaukee. The home is the 1846 homestead of the William Butler family, making the home older than the State of Wisconsin! The 2019 remodel of the Loft is in sophisticated farmhouse style and pays tribute to the history of the home in its furnishings, up cycled pieces, and beautiful setting. "Broken becomes blessed" both tells and compells as an invitation to all.

Guest favourite
A spacious suite is shown with a comfortable bed against the wall, accompanied by a cozy seating area featuring a gray couch. A decorative wall art piece adds character, while natural light filters in through the window, illuminating the warm wood flooring.
Guest suite in Waukesha
4.94 out of 5 average rating, 17 reviews

Inlaw Suite with Downtown Charm

Unbeatable Historic Downtown location. Duplex-like entry to your key-access 300sf downstairs suite, full kitchen/bath, standard queen bed w/ memory foam mattress. Walk a quiet neighborhood, <1 mile to the art hub of downtown - enjoy the summer farmer's market, or walk along Fox River! Minutes from convenience/department stores/more parks, 10 mins to I-94, <20 min to Pewaukee lake, <30 mins to Milwaukee/ airport/Lake Michigan. *NOTE: Ceiling is 6ft 7 inches.* NOTE: No pets allowed.*

Guest favourite
A brightly colored living area features an orange couch with patterned cushions, complemented by a unique coffee table. A round ottoman sits nearby, while large windows allow ample natural light. Open shelving holds decorative items, enhancing the vibrant atmosphere of the open-concept space.
Home in Bay View
4.94 out of 5 average rating, 122 reviews

Bright 1.5BR in the Heart of Bay View - w/ Parking

Perfectly located in Milwaukee’s eclectic Bay View 4 blocks from the lake. Minutes from downtown, Summerfest, art museum, etc. You’ll have the entire second floor of this sunny duplex. The space is open concept - 1 bed with a King Casper mattresses, a bright kitchen with tons of space, a stylish living room with art throughout, and an office (with an air mattress). Fenced-in back yard that's great for pets and chill around the outdoor table for optimal hangs and BBQs.

Guest favourite
A cozy living area features a blue sofa with cushions, a coffee table, and a large area rug. A wall-mounted Roku TV is visible, alongside a lamp and an air conditioning unit positioned beneath a window with dark curtains.
Apartment in Wauwatosa
4.93 out of 5 average rating, 72 reviews

Next to St Camillus, Froedtert, MCW & Childrens

Step into the stylish 1BR 1Bath 2nd Floor apartment near Milwaukee. Ideal for couples, traveling nurses, students, and business travelers.Across the street is St. Camillus, and we are a five minute drive from Froedert Hospital, Medical College of Wisconsin and Childrens Hospital. You can also walk to Milwaukee Zoo! ✔ King Bed ✔ Fully Equipped Kitchen ✔ High-Speed Wi-Fi ✔ Free underground Parking ✔ Dedicated Workspace ✔ Roku Smart TVs ✔ Covered Parking (Garage) + Elevator

Popular amenities for Waukesha vacation rentals

When is the best time to visit Waukesha?

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Frequently Asked Questions

  • How much does it cost to stay in house rentals in Waukesha?

    Experience the best of Waukesha with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there house rentals with a dedicated workspace in Waukesha?

    Yes! Work meets play with ease at over 10 house rentals in Waukesha featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Where should I stay in Waukesha?

    Make yourself at home in Waukesha by choosing from our most frequently booked neighborhoods. We have over 30 vacation rentals in Meadowbrook Heights, over 60 vacation rentals in Thielemans Heights, and over 10 vacation rentals in Springbrook.

  • Do house rentals in Waukesha have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Waukesha. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Waukesha?

    Waukesha has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Waukesha have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Waukesha. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Waukesha?

    Four-legged friends are welcome in Waukesha. Choose from more than 10 vacation rentals for guests traveling with pets.

  • What are the most popular amenities for House Rentals in Waukesha?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with air conditioning, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Waukesha

  • Total vacation rentals

    Explore 50 vacation rentals in Waukesha

  • Nightly prices starting at

    Waukesha vacation rentals start at $41 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,380 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    50 of Waukesha vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Waukesha rentals

  • 4.7 Average rating

    Waukesha stays receive an average rating of 4.7 out of 5 from guests

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