Vacation rentals in Waukesha

4.85 out of 5 average rating, 133 reviews

A lakeside view of a vacation rental home is visible, situated on a spacious lawn surrounded by trees. A private dock extends into the calm waters of Lake Sinissippi, reflecting the serene landscape and clear sky.

Home in Juneau

Take a Break at Lakeside Acres

Lakeside Acres; a 2-bedroom, 1 bath vacation rental home located on beautiful Lake Sinissippi. Open concept living area with furnished patio and private dock. This newly updated home provides the perfect summer getaway or winter retreat for family and friends. Whether you spend your days kayaking with the complimentary kayaks, exploring Horicon Marsh, or soaking up the sun on the dock, you're sure to have an unforgettable stay in this lakefront hideaway. Note: Docks are not in the lake Nov-Apr.

4.97 out of 5 average rating, 349 reviews

Apartment in Cedarburg

Cedarburg 2 br Apartment on prime Washington Ave

Prime location in Historic Cedarburg on Washington Ave in the heart of it all in a 2br apartment w/NO CLEANING FEE(short to do list at checkout).Guests get special attention that they deserve in a stylish calm space, above a 3 car garage accessed by stairs set back off of the street for a quiet timeout. So much to do & see or simply take a walk/picnic in the park. Just steps to shops, restaurants, wineries, & breweries set back off the street. Close to bike/hike trails, golf, museums, parks...

4.98 out of 5 average rating, 206 reviews

The image captures a serene view of Lake Como, showcasing clear water that transitions from a rocky shoreline to deeper hues. The gentle waves reflect the blue sky, creating a tranquil atmosphere with wooded areas visible along the opposite bank.

Condo in Lake Geneva

Lake Geneva Cloud 9

A resort community with outdoor pool (open during the summer season only) boat launch, tennis courts and small craft rentals on the premises. Beautiful views of Lake Como from the patio. Five minute drive to Downtown Lake Geneva. Free parking and keypad entry. Walk to The Ridge Hotel Resort and enjoy the use of their amenities for a small user fee which includes indoor and outdoor pools, spa, whirlpool, fitness center and restaurant. The condo is comfy and ready to make your stay memorable.

4.97 out of 5 average rating, 235 reviews

A modern mini kitchen features gray cabinetry and stainless steel appliances, including a refrigerator and microwave. A spacious custom island with natural wood finish is accompanied by four brown seating chairs. Under-cabinet lighting enhances a functional cooking area, with cookware and utensils visible.

Condo in Racine

Gorgeous Main Street Apt with Lake Views (APT2)

Gorgeous, open concept Main Street apartment on 3rd level, with views of downtown and partial views of the lake and harbor. New mini kitchen with 2 induction stove top burners, a microwave, toaster, and all the cookware and utensils needed for a getaway. Supersize custom island, comfy furnishings, and convenient to everything downtown. Unique building is connected to parking garage. Drive up to the 3rd floor - walk just 10 steps to your door - enjoy the views from above, without the climb.

Apartment in Port Washington

4.91 out of 5 average rating, 139 reviews

Lighthouse View -a real gem on Sweet Cake Hill

Enjoy the view of the Port Washington Lighthouse, Marina, and Lake Michigan from your private 1 queen bedroom (plus 2 futons in Living room) upper bungalow apartment. Our house was built in 1900 it has older architectural features. Please look at all the pictures. Private entrance, bathroom, and kitchen with range and refrigerator. Living room has plenty of seating and smart TV. Two block walk to the downtown with 17 restaurants and pubs within walking distance. Only 3 blocks to the marina!

4.97 out of 5 average rating, 144 reviews

A serene pathway lined with lush greenery features tall trees and blooming flowers. An inviting red chair is positioned in the background. A friendly sign indicating 'KEEP RIGHT' guides guests along the landscaped route toward the cottages.

Bungalow in Lake Geneva

Private Cozy Cottage Lake Geneva, WI

Come stay at our top rated Bed & Breakfast, located two blocks from the beautiful Lake Geneva. Relax in our California king suites, each contains a spa tub and shower, with heated floors and towel rails in the bathroom. Your complimentary breakfast basket is placed in your fridge prior to arrival, as well as complimentary gift of wine & cheese. Free WIFI is available on the property. No Pets, ADULTS over 21 ONLY. *NOTE all guests are required to pay a 8% Lake Geneva Bed Tax at check in.

4.98 out of 5 average rating, 145 reviews

Updated luxury country getaway short walk to lake!

Luxury getaway close to private beaches, downtown Lake Geneva, and many area amenities. Relax in comfort in this newly renovated 3-bedroom. Enjoy all that the Lake Geneva area has to offer while unwinding in a modern, comfortable retreat. Conveniently located a 3-min walk to Lake Como and a 10-min drive to downtown Lake Geneva. Charming golf cart community with so much to do. Perfect for couples, families, and business travelers. Ideal space for up to 4 adults and great for families of 5.

Superhost

Home in Kenosha

4.92 out of 5 average rating, 272 reviews

Where Family & Friends Gather to Create & Remember

Come gather, relax & celebrate at our 1 acre estate near beaches, dining & Carthage College! The designer interior features 5 BR/4 Bath, chef's kitchen with Viking & Subzero, Coffee/Espresso Bar, dining area for 12, 2 spacious family rooms with piano, fireplace and TVs. Enjoy dining, lounging & fun in the great outdoors w/hot tub, fire pit, basketball, pickleball, ping pong & lawn games! Beaches are walkable under a mile & near lively downtown w/ harbor, restaurants, shopping & museums.

4.88 out of 5 average rating, 106 reviews

Cabin in Fort Atkinson

Cozy Lake Cottage With The Best View & Pontoon!

Location, Location, Location! Incredible views! Retreat to this cozy Lake Koshkonong cottage with vaulted ceiling and southern exposure. Enjoy spectacular sunsets and views of the 10,000 acre lake from the north shore. Fish, hunt, boat, ski, swim, snowmobile, or simply soak up the sun and take in the view from this quiet retreat on a dead-end street. Fresh paint, bedding, and furniture make this little gem very comfortable. Great Walleye ice fishing right in front of this property!

4.98 out of 5 average rating, 146 reviews

An outdoor fire pit surrounded by wooden benches and chairs is visible in a spacious green area. The cabin in the background features a red exterior and large windows framed by trees, offering a serene spot for gathering.

Home in Elkhorn

Red Lodge - Game Room, Hot Tub, Near Lake

Looking for a memorable Wisconsin vacation experience? The Red Lodge is the ideal blend of comfort and style. Super clean, fully stocked, with gorgeous outdoor green spaces and unique amenities, you'll love it here! Jeff - "The devil is in the details, and no detail is overlooked here." Kelsey - "We are obsessed! This is THE nicest Airbnb we've stayed in across the country.. There was something truly unique about each room." Alia - "Hands down the best Airbnb we have ever stayed in."

4.9 out of 5 average rating, 147 reviews

A comfortable living area is highlighted by a soft sofa and armchair, accompanied by a stylish coffee table. A wall display features a cityscape artwork, while a lamp provides warm lighting. Natural light enters through large windows, enhancing the welcoming ambiance.

Home in West Allis

KING BED/Amazing Location/Free parking/Wi-Fi

Enjoy a fun and relaxing stay with family or friends in this stylish, cozy, and comfortable lower unit, which features: 2 bedrooms (1 king, 1 queen ) 1 bathroom Fully equipped kitchen with dining table and designated coffee bar Living room with a 65” smart TV (Netflix included) Home office space Free parking spot Located just a short drive (4 min) from I94, this home offers easy access to all the city's major attractions * the ideal base for exploring the best of Milwaukee

The exterior of the Clean Slate is characterized by a dark wooden façade and a welcoming front porch. A paved walkway leads to the entrance, flanked by neatly landscaped grass and flower beds. A large tree provides shade, enhancing the outdoor appeal.

4.94 out of 5 average rating, 34 reviews

The Clean Slate, Walk to down town, pet friendly

The Clean Slate is the latest offering from Lake Geneva luxury Rentals. Half mile walk to downtown. Pet friendly The house can accommodate 8 guests, but can be rented with its sister property, The White House, to accommodate larger groups. Contact host to inquire about renting both houses. This newly built home will surely delight. Tastefully decorated with all modern amenities. Easy access to downtown Lake Geneva’s shops, restaurants, Riviera Beach, and Geneva Lake Shore Path.

Vacation rentals for every style

Get the amount of space that is right for you

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Spaces that are more than just a place to sleep

Popular amenities for Waukesha vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Waukesha's top sights

The Corners of Brookfield8 locals recommend

Taylor’s People’s Park8 locals recommend

Texas Roadhouse5 locals recommend

Other great vacation rentals in Waukesha

Superhost

The kitchen features white cabinetry and a spacious island with seating. Stainless steel appliances, including a refrigerator and oven, are positioned for convenience. Soft lighting from pendant lights enhances the neutral tone, and a window allows natural light to fill the space.

4.94 out of 5 average rating, 16 reviews

Large Geneva Home | 8 beds | Fenced Yard Walkable

4.85 out of 5 average rating, 20 reviews

Guest suite in Wind Lake

Secret Garden Getaway

4.93 out of 5 average rating, 101 reviews

Home in Lake Geneva for your whole family

Superhost

A long horizontal painting hangs on a beige wall, depicting gentle waves and three sailboats on a serene blue sea. The sky is bright with soft clouds, and the shoreline features scattered birds, creating a calming coastal scene.

Home in West Allis

4.77 out of 5 average rating, 154 reviews

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

A well-equipped kitchen features light-colored cabinetry and ample counter space, with barstools positioned at the countertop. The room is illuminated by natural light from the windows, highlighting appliances and kitchen essentials, providing a functional and inviting cooking area.

4.91 out of 5 average rating, 117 reviews

Lake Geneva cottage with private beach access

4.92 out of 5 average rating, 346 reviews

Cabin in Trevor

Living the Lakehouse Dream

4.97 out of 5 average rating, 38 reviews

A welcoming entrance features a blend of natural wood paneling and decorative glass blocks. A door with large panes provides an inviting view of the outdoor space. The floor showcases a unique pattern, contributing to the home's mid-century modern aesthetic.

Home in Racine

Mid-Century Modern Dream Getaway