House vacation rentals in Whitefish Bay

4.92 out of 5 average rating, 132 reviews

A spacious living area features a cozy tufted sofa adorned with decorative pillows, complemented by a circular glass coffee table. A vibrant area rug with floral patterns enhances the warm wood floors. Colorful artwork decorates the walls, adding a playful touch to the room.

Home in Bay View

2BR Sunny Upper in Prime Bay View - w/ Parking

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

4.95 out of 5 average rating, 164 reviews

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

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.

A uniquely decorated bathroom features a white sink with a black rim, positioned beneath an oval mirror. Bright tropical wallpaper displays vivid greenery and animal motifs. A yellow towel hangs on a gold ring, and a white toilet paper holder is positioned nearby.

4.88 out of 5 average rating, 161 reviews

The Prospect House - Shorewood / Milwaukee, WI

From activities and attractions to fairs and festivals, Milwaukee, has something for everyone in your travel group! After each adventure-filled day, look forward to returning to this 3-bed, 1.5-bath lower duplex house featuring a fully equipped kitchen, bright living space, classic creaky wood floors, comfy accommodations for 6. There's a variety of things to do in MKE including award winning dining, pro Sports, Brewery tours, music festivals and more! Indoors or outdoors, the fun is endless!

4.94 out of 5 average rating, 158 reviews

An open concept kitchen features a large white island with seating, accompanied by modern cabinetry. The living space extends into a bright dining area, enhanced by natural light from a window. Decorative artwork and a wall clock add character to the surroundings.

Home in Halyard Park

Downtown Oasis: Hot Tub, Garage, 2 King Huge yard!

Bring the whole family to this great place with lots of room for fun. A rock throw away to Milwaukee central featuring the city's best restaurants, bars, shops, and attractions. This exclusive 1800sqft Ranch 3 bedrooms, 9 beds, 2 full and 1 half bathrooms to sleep up to 14 guests. It features everything your family & friends need: Large Kitchen, Wash/Dry, Outdoor Patio, large back yard and a 8 person Hot Tub! Walking to the Fiserv Forum and downtown. Attached Garage w/ Driveway. 1 Gig Internet

The living room features a comfortable sectional sofa and a light-colored couch, accented with colorful pillows. A round wooden coffee table sits at the center, complemented by a decorative rug. Natural light filters through large windows with stained glass detailing.

4.99 out of 5 average rating, 115 reviews

The Menlo Guesthouse

A vintage, lower flat in a 100-year-old duplex with modern comforts and conveniences. Perfect for short or long stays while visiting Milwaukee. Situated in the walkable/bikeable Milwaukee neighborhood of Shorewood. The flat is located just a few blocks north of UWM and a few blocks east of the Oak Leaf Trail. Three minutes from Atwater Beach. Ten minutes or less to Bradford Beach, museums, and Summer Fest. Fifteen minutes or less to Fiserv Forum, Panther Arena, and American Family Field.

4.98 out of 5 average rating, 135 reviews

A historic cottage is set amidst lush greenery, featuring a mix of stone and siding on the exterior. A gravel driveway leads to the entrance, surrounded by well-maintained landscaping and mature trees that provide a tranquil atmosphere.

Home in Mequon

Historic cottage with fireplace. Pets Welcome!

Step back in time and immerse yourself in the charm of our historic 3-bedroom cottage, part of the renowned Jahn Farmstead, proudly listed on the National Register of Historic Places. Built in the mid-19th century, this Greek Revival-style farmhouse offers a unique blend of historical elegance and modern comfort, ensuring a relaxing and memorable stay. Located 2 miles from the Mequon Public Market and 5 miles from Cedarburg. Pets are welcome and we have acres of land for you to explore!

A cozy living area is presented with two dark leather sofas, accompanied by bright red cushions. A glass coffee table occupies the center, while light enters through two large windows adorned with navy blue curtains. A stylish lamp and a decorative piece complete the room.

4.9 out of 5 average rating, 278 reviews

Historic East Side Duplex, 3BD. No Cleaning Fee!

Minutes from downtown Milwaukee by car or bus, the whole group will enjoy easy access to the city from this central location less than a mile from the UWM campus. A block from the Urban Ecology Center and Oak Leaf Trail access and easy walking distance to North Avenue's restaurants, bars, and the Oriental Theater, there's no shortage of activities, entertainment, and dining options around this historic and charming East Side abode. Or stay in with our grill and fire pit.

A well-equipped kitchen features white cabinetry, stainless steel appliances, and green tile backsplash. The space is illuminated with recessed lighting and includes a dining area with a wood table. An open doorway leads to another room, enhancing the overall flow of the layout.

4.95 out of 5 average rating, 127 reviews

Shorewood house - near shops w/ WiFi & parking

Just down the road from Lake Michigan, this charming duplex upper is the perfect space for a relaxing getaway. After a day of shopping, eating good food, and exploring Milwaukee, look forward to kicking back in the cozy living room, or on the patio. This duplex has 2 bedrooms; a King bed master, and one bedroom with two Twins. There is one charming bathroom with a bathtub. Well stocked kitchen, and plenty of backyard space. The lower tenant is respectful of guests.

A welcoming hallway is displayed, featuring light-colored walls and a combination of wooden and tile flooring. An ornate mirror hangs on one wall, while decorative hooks are mounted nearby. Natural light streams in through a window beside the front door, enhancing the inviting atmosphere.

5 out of 5 average rating, 122 reviews

Bright Eastside MKE cottage w/ FREE Parking

Welcome to our peaceful little cottage in the heart of Milwaukee. This adorable 2 bedroom, 1 bathroom home will meet all of your needs with 1 king bed, 1 queen bed, a fully stocked kitchen, wifi, driveway for off street parking, and bikes to use on the nearby Oak Leaf Trail. This is the perfect place to enjoy the friendly city of Milwaukee with a comfortable place to sleep at the end of the day. Enjoy all of the restaurants and shops on the Eastside of Milwaukee.

4.78 out of 5 average rating, 132 reviews

An outdoor area features a hot tub and a fire-pit surrounded by several white Adirondack chairs. A spacious wooden deck is visible, along with a well-maintained lawn and trees providing a natural backdrop.

Home in Glendale

Retro Riverside Retreat, Backyard Oasis, Hot Tub

Escape to the retro riverside retreat! This large home sleeps 16+ and offers an incredible outdoor area with a hot tub, fire-pit, and river access. Your outdoor oasis and awaits. Inside, enjoy 6 bedrooms, 3 bathrooms, a huge dining table, and a game room. Perfect for large groups, family gatherings, or a peaceful oasis. Just a short 15-minute drive to vibrant Milwaukee attractions. Experience relaxation and adventure in our remarkable riverside getaway.

4.97 out of 5 average rating, 127 reviews

A spacious dining area features a wooden table surrounded by six chairs, complemented by an archway leading to a cozy living room. Natural light filters through large windows, illuminating the elegant combination of exposed brick and light-toned walls.

Home in Wauwatosa

Historic on The Avenue

Entire Home- 3 bedrooms This beautiful historic home is centrally located in the heart of Wauwatosa! Steps from the quaint village with restaurants, bars, coffee shops and boutiques! This property marries old world charm with modern amenities. Less than 15 minutes via freeway to downtown Milwaukee, the lakefront, Marquette University, less than 10 minutes to American Family Field, 5 minutes to the Milwaukee Zoo and Froedtert/Children's hospital.

4.97 out of 5 average rating, 104 reviews

An outdoor area features a comfortable seating arrangement around a modern fire pit. A dining table with chairs is positioned nearby, with an umbrella providing shade. String lights are strung above, enhancing the cozy atmosphere of the fully fenced backyard.

Home in Murray Hill

Charming Pet-Friendly 3-BR Home, Firepit, Backyard

Welcome to Belleview House, a delightful pet-friendly 3-bedroom home nestled in the heart of the vibrant Murray Hill/East Side neighborhood. Renovation coming! Upgrades include hot tub, indoor refresh and added amenities - coming December 2025. ✔ Comfy Queen Beds ✔ Fenced Backyard with Outdoor Fire Pit ✔ Outdoor dining table ✔ 0.9 mi to Bradford Beach on Lake Michigan ✔ Stocked Kitchen ✔ Smart TV ✔ High-Speed Wi-Fi ✔ Workspace

Popular amenities for Whitefish Bay house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.94 out of 5 average rating, 170 reviews

A historic Victorian-style home is showcased with a blue exterior and ornate architectural details. Bright green foliage frames the entrance, leading to the front steps. The sky is clear, enhancing the home's inviting appearance.

Home in Brewer's Hill

Brewers Hill Gem w/hot tub & seasonal shared pool

4.95 out of 5 average rating, 43 reviews

A single-story house is presented with a light exterior and a welcoming porch. A shaded area is provided by the overhanging roof, and a bench is positioned on the porch. A well-maintained lawn stretches in front, framed by lush green trees.

Home in Delafield

Cute and cozy 2 bedroom house perfectly located!

5 out of 5 average rating, 54 reviews

Two black Adirondack chairs and a small side table are positioned on a patio, overlooking a lush green landscape under a cloudy sky. The view encompasses rolling hills and tree foliage, providing a serene outdoor setting.

Home in Lake Geneva

Newly Updated Modern Lake Condo

4.5 out of 5 average rating, 6 reviews

An indoor heated pool is featured, surrounded by smooth concrete flooring. A ladder provides access, while a basketball hoop stands beside the pool. Large windows allow natural light to illuminate the space, offering views of the outside landscape.

Home in River Hills

River Hills 90210

4.89 out of 5 average rating, 18 reviews

A cozy living room features a light-colored sectional sofa complemented by colorful throw pillows. A plush, vibrant area rug adds warmth to the space. Two windows with light-filtering shades allow natural light, while a recliner and wooden table provide additional seating and surface space.

Home in Riverwest

Big BLUE Skyline VIEW

4.95 out of 5 average rating, 95 reviews

A spacious living area features comfortable gray sectional sofas adorned with turquoise cushions. A light wooden coffee table is centered on a soft area rug. Soft lighting is provided by table lamps, and large sliding doors lead to an outdoor space with a view of greenery.

Home in Lake Geneva

Relaxing getaway/StepsToLake/Pool/Tennis/nearDT/WD

5 out of 5 average rating, 9 reviews

The backyard features a large in-ground pool surrounded by a wooden deck, adorned with comfortable seating areas and a pergola. Lush greenery frames the space, contributing to a peaceful atmosphere. Sunlight reflects off the water, offering a refreshing contrast to the well-maintained surroundings.

Home in Lake Geneva

Oasis on Oak | Private In-Ground Pool | Hot Tub

4.89 out of 5 average rating, 125 reviews

An indoor pool area is showcased, featuring a large, clear pool with a projector screen positioned above. Natural stone walls and wood beams enhance the space, complemented by soft lighting. Large windows allow natural light to brighten the inviting environment.

Home in Sussex

Wooded Hills/Indoor Pool/Hot Tub/Arcade

Weekly house rentals

4.92 out of 5 average rating, 62 reviews

A cozy living area features a soft blue sectional sofa arranged around two modern, geometric coffee tables. Natural light enters through large windows adorned with light curtains, illuminating the space. A welcoming entryway is visible to the side, enhancing the inviting atmosphere.

Home in Glendale

Retreat w/hot tub Fmly/Pet Frdly No Clean fee

The exterior of a two-story duplex is shown, featuring a combination of light and dark siding. A welcoming entrance is flanked by greenery and flower pots. A small balcony is visible on the upper level, enhancing the home's character and charm.

5 out of 5 average rating, 48 reviews

Lovely 3 bed near Lake Michigan

4.94 out of 5 average rating, 31 reviews

A warm, open layout showcases a rustic kitchen with wooden accents and a spacious counter. Three high stools are arranged at the bar area. Natural light fills the space, highlighting the cozy living area with a fireplace and inviting decor.

Home in Glendale

Bass & Sparrow - Spa Retreat on the MKE River

A cozy living area features a sectional sofa with a textured throw and decorative pillows. A wooden coffee table with a glass bowl sits in front, surrounded by windows that allow natural light to brighten the room. Warm tones are complemented by a patterned area rug.

4.99 out of 5 average rating, 83 reviews

East Side 2nd floor Gem

A light-filled living room features large windows letting in natural light. Two soft sofas and a patterned area rug create a comfortable seating area. A side table and a dark wood bookshelf enhance the space, complemented by decorative cushions in soft colors.

4.94 out of 5 average rating, 33 reviews

Whitefish Bay Getaway; steps from Starbucks!

A spacious living area is showcased with a modern sectional sofa and a marble-top coffee table. A large flat-screen television is mounted above a decorative fireplace. Natural light filters through multiple windows, illuminating the light-colored walls and warm wood flooring.

5 out of 5 average rating, 41 reviews

4 Mins Walk Lake Michigan Atwater Park Beach. Pets

A charming brick exterior features green shutters and a welcoming front door. The landscaped yard includes well-maintained grass and flower beds, complemented by a paved driveway leading to a garage. Two wooden chairs are positioned on the lawn, inviting relaxation.

5 out of 5 average rating, 11 reviews

Beautiful 3+ Bedroom Home Close to Milwaukee

A bright living area features a cozy orange couch, two comfortable chairs, and a large patterned rug. A white brick fireplace serves as a focal point, while tall windows allow natural light to fill the space. An archway leads to another room, showcasing airy elegance.

4.77 out of 5 average rating, 13 reviews

Amazing Family Home in Whitefish Bay!

Private house rentals

5 out of 5 average rating, 4 reviews

Home in Milwaukee

Spacious house • Sleeps 8• Mins Downtown• Garage

5 out of 5 average rating, 12 reviews

The exterior of a National Historic home is shown, featuring a stone facade with a distinctive roof and multiple windows. Lush greenery surrounds the entrance, and a curved pathway leads to the front door, framed by vibrant flowering plants under clear blue skies.

Home in Downer Woods

Tranquil Storybook Cottage near UWM

4.92 out of 5 average rating, 72 reviews

A spacious living area is presented with modern seating arrangements, featuring two armchairs and a comfortable sofa. Natural light fills the room through large windows, and a gas fireplace adds warmth. A stylish dining table accommodates multiple guests, complementing the inviting atmosphere.

Home in Riverwest

Heart of MKE-Private Backyard-Free Netflix-BBQ

5 out of 5 average rating, 31 reviews

A comfortable living room is depicted, featuring a tan leather sofa and a matching accent chair. A coffee table sits on a light area rug, and natural light filters through large windows. A wooden piano and wall art add character to the space.

Home in Wauwatosa

Beautiful safe quiet home in great location

A cozy living room is presented, featuring a comfortable gray sofa adorned with decorative pillows. A round coffee table sits in front, and an assortment of natural light streams through multiple windows. A wooden play structure is visible, alongside various plants and artwork.

4.81 out of 5 average rating, 54 reviews

Baby and Toddler friendly House by the Beach

A dining area features a round table with green chairs, surrounded by natural light from nearby windows. An inviting sitting area includes a large chair made of woven materials. A cozy bathroom showcases a shower curtain with a subtle pattern. An outdoor patio displays a table with yellow accents.

4.93 out of 5 average rating, 15 reviews

Gorgeous space with huge porch.

An outdoor deck is presented with a round table surrounded by four striped chairs. A large umbrella provides shade, and green foliage serves as a backdrop, offering a serene outdoor space for relaxation.

4.95 out of 5 average rating, 22 reviews

Whitefish Bay 3Bedroom Entire House Sleeps 4