Holiday houses in Whitefish Bay

4.91 out of 5 average rating, 116 reviews

A spacious living area features a large smart TV mounted on the wall, with modern furniture arranged for comfort. A sectional sofa and accent chair provide seating options. Natural light streams through the windows, and artistic touches enhance the welcoming atmosphere.

Apartment in Shorewood

Charming home w/ fire pit, walk to Lake Michigan

Welcome to our home in a quiet neighborhood, a short walk to gorgeous views over Lake Michigan and two blocks to restaurants, shopping, and nightlife. Gather around the fire pit and grill dinner in the back patio. Listen to our vinyl collection or stream your own music while playing board games next to the smart TV. Super-fast internet, a fully equipped kitchen with coffee & tea, and in-unit laundry. Two comfy queen beds + a sleeper sofa. Here with kids? We have toys, a Pack n' Play, & more.

ValueFamilyAir conditioning

5.0 out of 5 average rating, 22 reviews

Robin's Bluff

Nestle into this serene 3-bedroom home with vintage charm and modern appeal. Enjoy a cozy book in bed, a relaxing movie night in the living room, or an exciting evening in the rec room--stocked with puzzles, board games, darts, and more. Fancy cooking brekky before driving a few minutes to Milwaukee or walking to the downtown? Our kitchen features a casual breakfast nook, in addition to the formal dining room. Don't miss this picturesque stay in the quiet and historic Village of Whitefish Bay.

FamilyLocationNearby

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, 184 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!

FamilyValueBathroom

Superhost

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.

4.82 out of 5 average rating, 17 reviews

Amazing Family Home in Whitefish Bay!

Welcome to this recently renovated four-bedroom Tudor home on a beautiful tree-lined street in the heart of Whitefish Bay, just a few blocks from parks, coffee shops, restaurants, and the beach at Lake Michigan. Just a 15-minute drive down scenic Lake Drive to downtown Milwaukee. Features four bedrooms, two full bathrooms and a powder room, with a fully finished basement perfect for kids’ play space or watching the game. Spacious fenced backyard with a patio, grill, and outdoor furniture.

FamilyLocationAccess

4.95 out of 5 average rating, 114 reviews

Home in Milwaukee

Brew City Inn with Hot Tub | Summerfest House

Welcome to another property by “GNRHomes”! Make some memories at this luxurious, unique and family-friendly residential home on a quiet street. Newly renovated 1900’s home with both historic charm and modern luxury. Walkable to many major bars and restaurants. A few minutes to most popular MKE attractions, DM for more info. By booking this home you have access to the entire space and private hot tub with an garage oasis. Great central location to discover all that Milwaukee has to offer.

LocationValueComfort

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.

5.0 out of 5 average rating, 15 reviews

Beautiful 3+ Bedroom Home Close to Milwaukee

Lovely 3 bedroom home with 2 full baths and a partially finished basement with a sofa sleeper and 1/2 bath. Whitefish Bay is a quiet, safe, upscale suburb of Milwaukee, close to beautiful Lake Michigan. There is easy access to downtown Milwaukee and surrounding areas via car, bike, or public transportation. Lots of wonderful dining, shopping, and recreational activities nearby. I have been an Airbnb Super host for the past 8 years. Please read the other details section for more information.

LocationFamilyWalkability

An elegant dining room is seen through a graceful archway. A dark wooden table is surrounded by six chairs, while a shimmering chandelier hangs above. The walls are painted in a warm orange hue, complemented by a classic area rug and large windows that allow natural light to enter.

4.91 out of 5 average rating, 74 reviews

Prairie style home on Stratford

Unique Arts and Crafts lower flat with turn of the century charm. Natural cherry woodwork with a spacious living and dining area—with seating for 10. Includes three bedrooms – one with a king bed, and two with queen beds. Updates Includes a modern kitchen, bath and shower, washer/dryer, and central air. Additional features include high-speed Internet with meshed WIFI, a 65" 4K TV, full surround sound—and Roku. Outdoor patio has seating for 12+, a Weber Summit grill, great for entertaining!

FamilyValueBackyard

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, 145 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.

ValueFamilyCheck-in

Apartment in Whitefish Bay

A welcoming living area features large windows allowing natural light to fill the room. A light-colored sofa is positioned alongside a round coffee table. A modern lamp stands nearby, and a potted plant adds a touch of greenery. A flat-screen TV is mounted on the wall.

Shorewood's Sunny Craftsman

Welcome to our beautiful, sun-filled, 2-bedroom flat in the amazing lakeshore community of Shorewood! Fully updated in 2023, this lower duplex unit is on a quiet block, and just two blocks from all the wonderful shops, restaurants, and bars on Oakland Ave. Shorewood is very walkable community, with parks, green spaces, beaches, and beer gardens within walking distance. Take advantage of the fully-stocked kitchen with stainless appliances, including dishwasher. Come visit us today!

LocationFamilySleep quality

5.0 out of 5 average rating, 62 reviews

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.

4.96 out of 5 average rating, 45 reviews

Whitefish Bay Getaway; steps from Starbucks!

Stay in our beautiful, fully-equipped, family-friendly home in the heart of upscale Whitefish Bay! Coffee shops, restaurants, grocery stores, and local shopping just outside your front door. Within five blocks you'll find Lake Michigan, Bayshore Mall, and 5 different playgrounds. Located 7 miles from downtown Milwaukee, access the city easily via highway, Uber, direct bus line, or the picturesque Oakleaf bike trail. Freshly furnished, including new mattresses and linens.

LocationFamilyComfort

4.93 out of 5 average rating, 321 reviews

The exterior of a brick building features a raised balcony adorned with a decorative banner. The structure displays a mix of rustic brick and stone arches, framed by green trim. Natural light illuminates the scene, creating a welcoming view of the entrance.

Condo in Shorewood

English Tudor - Upper Flat blocks from the beach

Sophisticated 100 Yr Old English Tudor Upper Flat with hardwood floors, crown moldings, sunken living room, natural fireplace, built-in bookcases, and fully furnished. Spacious 2200 sq. foot 2nd-floor unit. Safe and QUIET neighborhood just blocks from Atwater beach. Cats are on the property and do not go any guest space. Make sure you have the correct number of guests on your reservation request. Bookings on a Friday or Saturday are required to include both nights.

LocationFamilyParks

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.

4.96 out of 5 average rating, 25 reviews

Whitefish Bay 3Bedroom Entire House Sleeps 4

1 QUEEN and 2 Single Beds (three beds total) We accept longer stays, but in 28 day increments. Steps from Lake Michigan, this cozy Cape Cod will be your home away from home, while your family explores all that Milwaukee has to offer. Please know that we are not a big corporation with multiple rentals. We lived in Whitefish Bay for 23 years and recently had to move due to a job change. REWARDS DISCOUNT FOR FREQUENT USERS OF AIRBNB! High Speed Fiber Optic WiFi (AT&T)

LocationFamilyAccuracy

Popular amenities for Whitefish Bay holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Whitefish Bay

5.0 out of 5 average rating, 36 reviews

The kitchen features green cabinetry and a white backsplash, creating a modern aesthetic. A gas stove, microwave, and refrigerator are readily visible. Countertops are crafted from wood, and utensils are neatly organized, while a patterned floor adds a unique touch.

Apartment in Shorewood

The Little Blue Bungelow

LocationFamilyQuiet

4.92 out of 5 average rating, 12 reviews

The living room features a smart TV mounted above a traditional fireplace, framed by elegant woodwork. Comfortable seating options are provided, including a patterned armchair and a spacious couch. Natural light enters through decorated windows, enhancing the room's inviting atmosphere.

Home in Glendale

Historic Glendale Bungalow Retreat with Game Room

LocationFamilyCleanliness

A hot tub situated on a patio glows with soft blue lighting, surrounded by wooden fencing and greenery. Several individuals relax in the warm water, with steps leading up to the entrance of the home visible in the background.

4.85 out of 5 average rating, 92 reviews

Hot Tub Victorian Garden Home

LocationFamilyOutdoor spaces

5.0 out of 5 average rating, 20 reviews

The living room features a cozy arrangement of gray sofas adorned with decorative pillows and a warm throw. A black and white rug anchors the space, complemented by a coffee table displaying natural elements. A flat-screen TV and soft lighting create an inviting environment.

Home in Glendale

Cozy Single-family house

FamilyLocationComfort

Superhost

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

FamilyLocationBiking

4.92 out of 5 average rating, 79 reviews

4.96 out of 5 average rating, 55 reviews

4 Mins Walk Lake Michigan Atwater Park Beach. Pets

FamilyLocationSleep quality

Superhost

Home in Milwaukee

Historic Milwaukee Gem Near Lake Michigan and UWM

FamilyValueAccuracy

4.83 out of 5 average rating, 29 reviews

A spacious bedroom features a plush king bed adorned with soft bedding, complemented by decorative pillows. Natural light filters through two windows, with dark curtains offering privacy. A cozy leather chair is positioned beside a turquoise dresser, adding a stylish touch to the warm decor.