Vacation rentals in Waukesha

4.81 out of 5 average rating, 114 reviews

Guest suite in Bay View

Basement Bay View Suite,express bus airport-north

Bay View is a walking community. Our place is close to family-friendly activities, public transport, & the airport. You’ll love our place. It's a short walk to express bus from airport, past downtown, UW-M and to Bayside. Located across the street from Humboldt Park. We are about a 20 minute walk from Lake Michigan. Summerfest grounds a short bus ride away. Winter is fun in the park. Tobogganing (2), skates and cross country skis to use. Hope the sizes fit you. I find if one plays in snow ⛄️ 😌

4.91 out of 5 average rating, 171 reviews

A grand staircase features intricate wooden detailing and balusters, leading to the upper level. The entrance area includes a beautifully crafted wooden railing, a cozy seating area on the left, and decorative elements along the walls. Natural light filters through the nearby windows.

Home in Wales

Historic, Vintage, Classy, 12 bed, 6 bath!

This charming estate will make your special occasion a memory of a lifetime! It offers 5+ bedrooms all with their own baths, four w/private suites, 5 full baths + 2 half baths total. Suites offer a variety of whirlpool tubs, glass/tile showers and romantic gas FP's. Large main floor offers a huge kitchen with double oven, breakfast bar and two living rooms. Dining room, kitchen table and bar seat 20. LL offers a 6th bedroom with new queen bed, rec room with new 50" TV and three more twins.

Guest suite in Brookfield

A view of the well-maintained outdoor area is presented, showcasing a neatly paved pathway bordered by lush green lawns and mature trees. The scene is complemented by a clear blue sky, providing a tranquil atmosphere in a tree-filled neighborhood.

5 out of 5 average rating, 234 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!

4.79 out of 5 average rating, 257 reviews

A magazine titled 'The Solo Traveler' is positioned alongside a promotional card that reads 'WANT MORE MILWAUKEE?'. Both items rest on a surface adorned with water droplets, creating a textured backdrop that adds depth to the arrangement.

Home in Milwaukee

Private Milwaukee Home-Great Location, Entire Unit

This private upper level unit is only 3 miles from Froedtert Hospital, 1.1 miles from Mayfair Mall, and only steps away from Mount Mary University; bordering Wauwatosa, a suburb with great places to roam! This home is spacious, yet cozy. Offers a secure bedroom for 2, living room with a comfy sofa bed that sleeps one, dining area, bathroom, & full kitchen with all the necessities. A Key Less entry makes your check-in quick and easy! Minutes from the highway, making getting anywhere a breeze.

4.95 out of 5 average rating, 329 reviews

Apartment in Bay View

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.

4.95 out of 5 average rating, 139 reviews

A charming white cottage sits within a landscaped area, surrounded by a white picket fence. Lush greenery and flowering plants are visible in the foreground, while trees stand in the background under a clear blue sky.

Cottage in Hartland

Cozy cottage in the heart of Lake Country

Entire cottage in the heart of Lake Country. Merryhill Cottage is nestled on two acres with mature trees. Included on the two acres- the host's farmhouse, a guest house and barn. The feeling of a country setting but with easy access to Hwys 16, 83 and I 94. Close to shopping, restaurants, parks, hiking, cross country skiing and snowshoeing, lakes, and beaches (10 min. to Delafield and Oconomowoc and 15 min. to Pewaukee.) Perfect for day trips to Madison (54 min.) and Milwaukee (30 min.).

4.92 out of 5 average rating, 157 reviews

The modern kitchen features a large granite countertop with seating for two. A small dining area is visible, along with a television mounted on the wall. Natural light fills the space through the windows, complemented by dark curtains, and a green plant adds a touch of greenery.

Townhouse in Waukesha

Cozy 2BR charm | Big Yard, Fire pit, Replenishing!

Cozy gem sleeps up to 5. Renovated Interiors w/ large balcony overlooking serene yard. Enjoy an eastern sunrise during your morning coffee, or a starry night next to the warmth of a fire. 1 mile from 94 - 20 minutes from Milwaukee. Fully stocked kitchenette. Gas burning stove/oven, microwave, coffee maker, full size fridge/freezer, in unit washer/dryer, wifi, smart tv, wireless printer, private large balcony w/ heater for cooler nights. Perfect space for a couple or traveling profesional.

4.96 out of 5 average rating, 291 reviews

A well-equipped kitchenette is shown, featuring a stainless steel refrigerator, microwave, and a coffee maker. Above the countertop, mugs are neatly arranged on a hanging rack. A glass-paned door leads to another room, adding a touch of elegance with a chandelier visible through the glass.

Guest suite in Sussex

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.

4.99 out of 5 average rating, 143 reviews

An outdoor living space features a stone grill area beside a wood-burning oven, surrounded by lush greenery. Soft lighting from suspended bulbs adds warmth as the sun sets in the background, casting a gentle glow over the patio with a decorative stone surface.

Guest suite in Sussex

Garden Retreat in law Suite

Welcome to our in-law suite apartment featuring a full eat-in kitchen, living room, queen bed in large bedroom, walk in closet and full bathroom with walk-in shower. Our beautiful two acre yard has many areas to relax in, including a hammock and fire pit for the evenings. Twenty mins. to Erin Hills and Holy Hill and a half hour to most downtown Milwaukee attractions, as well as the RNC activities taking place this summer. Lots of city tips and suggestions for our guests.

4.85 out of 5 average rating, 328 reviews

A tiled shower space features natural stone walls in varying shades of gray. A built-in bench is positioned against the wall, and a white towel hangs from a metal towel bar. A bottle of shampoo is placed on the floor near the shower drain.

Apartment in Wauwatosa

Tosa Village Studio Apartment

Tosa Village Studio. (Wauwatosa is the first suburb west of Milwaukee). Walk to the Village and explore the boutique shops, restaurants and bars. Enjoy summer concerts in Hart Park. Miller Park (Milwaukee County Stadium - Home of the Brewers) only 3.5 miles away. Close to the Medical Complex, Froedert and Children's Hospitals. 6.5 miles to the Fiserv Forum (Home of the Milwaukee Bucks). Six miles to downtown Milwaukee. Enjoy Summerfest at the Lake Michigan shore.

4.96 out of 5 average rating, 182 reviews

A well-furnished bedroom features a spacious bed with a striped comforter. Two modern wall-mounted lamps flank the headboard, providing soft lighting. Natural light enters through a window, creating a bright and calming atmosphere. A nightstand and wastebasket complete the room's setup.

Apartment in West Allis

Clean 2 bedroom/1 bath close to everything!

Charming, recently and tastefully furnished 2 bedroom 1 bathroom apartment with private entrance and parking. Close to downtown, shopping malls, zoo, hospital, airport, and main freeways. Full kitchen with stove, microwave, coffee pot, toaster, and kitchenware. Unit has TVs and WiFi. Coin operated laundry is accessible in building. Why stay at a hotel when you can feel at home in this lovely unit?

Guest suite in Helenville

A warm fire burns brightly in a stone firepit, with flames dancing and casting light against the surrounding evening darkness. The full moon is visible in the night sky above, providing a serene contrast to the flickering flames. A stone bench can be seen nearby.

4.95 out of 5 average rating, 366 reviews

Chic Loft Surrounded by Nature

This charming shabby chic loft sits in the heart of the country between Madison and Milwaukee. The Lighthouse Farm is also a wedding/event venue (please inquire for more details) . A quiet relaxing environment, with lots of open space, natural sunlight and lush green landscape. Great for those looking to get away with easy access to metropolitan areas, lakes, rivers and hiking/biking trails.

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Popular amenities for Waukesha vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Waukesha

4.88 out of 5 average rating, 57 reviews

A spacious deck is shown featuring a circular table surrounded by six black, cushioned chairs. A green lawn with trees provides a scenic backdrop, while the clear sky enhances the inviting outdoor area.

Home in Waukesha

Cozy 3BR Ranch Home Away From Home

MardeeRating, 5 stars6 days ago

This is a lovely home! There is a sliding glass door, leading to a deck in a beautiful backyard. We really enjoyed eating our meals out there. The neighborhood is quiet, super clean, feels very safe—great for walks! Zelda is wonderful to work with. Our stay went off without a hitch!

4.92 out of 5 average rating, 59 reviews

An open living area features warm wood paneling and beams, enhancing a rustic ambiance. A spacious kitchen with wooden cabinetry is visible, alongside a cozy seating area furnished with a sectional and chairs. A dining table with four wooden chairs is positioned near a patterned area rug.

Home in Pewaukee

Rustic Charm: Pewaukee Lake Cabin, Sauna & Hot Tub

AlexandraRating, 5 stars2 months ago

The property is just lovely, especially if you value peace when outdoors. We were just as pleased with our stay. It was first time we stayed in Pewaukee. The town itself and the neighboring towns had plenty to do. Howevere, we found ourselves at the airbnb mostly between the hot tub and sauna there was plenty to do.

5 out of 5 average rating, 7 reviews

A spacious deck is visible with a variety of seating options, including four white Adirondack chairs and two blue lounge chairs. A fire pit sits centrally on the deck, and a grill is positioned nearby. Large windows provide a view of the surrounding environment.

Home in Pewaukee

Waterfront on Pewaukee Lake |3BR/2BA|Private Pier

CarolynRating, 5 stars4 days ago

My family had a wonderful visit! The boys fished right off the dock and caught some huge bass and a northern pike! The house was extremely clean and well stocked with everything you need to cook meals, relax and watch a movie, or enjoy the lake. We also enjoyed the use of the paddle boards and kayaks. Overall a great spot with WiFi in a great location. We didn’t visit any of the nearby restaurants but they are within walking distance. We were also able to bring our dog which was a great plus because we love to travel with him. We will definitely return. Kristen was a wonderful host and always checked in to make sure our stay was excellent. Thanks again for a fantastic vacation!

5 out of 5 average rating, 9 reviews

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

Designer Home w/ Lake Views + Walk to Beachfront

JasonRating, 5 stars1 week ago

What a wonderful stay! It’s was the living room and patio overlooking the lake that got us and it did not disappoint! The sleeping quarters and bathrooms were 5 star given comfort and amenities. While we did not use the garage due to the size of our vehicle, a huge plus that are driving personal vehicles. Jason and Melissa were very responsive with a few questions and guidance. While it was a homecoming for us, a definite recommendation for those that are visiting from out of town!

4.9 out of 5 average rating, 63 reviews

A serene garden area features twinkling string lights hung above a small round table and a chair, set on lush green grass. A wooden lattice fence provides privacy, while dense greenery surrounds the space, enhancing the peaceful atmosphere.

Guest suite in Wauwatosa

Private Tosa Guest Suite, Hidden Gem in Paradise

JQRating, 5 stars2 weeks ago

It’s a nice and clean room in a quiet neighborhood. The room was bigger than I thought and had everything I needed. Amanda was friendly and helpful. Totally recommended!

5 out of 5 average rating, 4 reviews

The exterior of the stone farmhouse features a charming fenced area with a patio, shaded by an umbrella. Large windows adorn the building, allowing natural light to illuminate the inviting stone facade. Lush greenery surrounds the entrance, enhancing the serene atmosphere.

Home in Waukesha

Farmhouse "The Inn"

SaraRating, 5 stars11 months ago

Beautiful and cozy historic location! We had a great time and Karen was a wonderful, responsive, and friendly host. Our group had a wonderful reunion there.

5 out of 5 average rating, 12 reviews

A modern kitchen is presented with bright cabinetry and sleek stainless-steel appliances. A central island with seating is highlighted, complemented by wooden beams above. Natural light is enhanced by large windows, and an inviting atmosphere is created with simple decor.

Cottage in Pewaukee

Lakeside Pewaukee Cottage

LaurelRating, 5 stars8 months ago

We were impressed by the cleanliness and open feeling of the place. It was a little smaller than we expected and had very limited seating but fit our group of 3 ok. I can’t imagine it being comfortable for a larger group though unless you’re only using the place to sleep! Overall it was a pleasant experience, beds were comfortable, kitchen well-appointed and the hot tub was nice, but we did feel that the price, once the cleaning fee was added on, was a little steep.