Family-friendly vacation rentals in Whitefish Bay

4.91 out of 5 average rating, 117 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.

4.88 out of 5 average rating, 184 reviews

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.

Home in Shorewood

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!

5.0 out of 5 average rating, 150 reviews

Modern Home Near Downtown | Rooftop Patio + Garage

Beautiful 2400 sq ft newer construction home located in Milwaukee's Historic Brewer's Hill neighborhood <1 mile from the heart of downtown. Perfect for large groups! -Open floor plan on main level - easy flow for groups! -Large rooftop patio with several seating areas + electric grill -4 bedrooms plus finished basement equipped with pullout sofa -3.5 bathrooms - 1 master shower, 2 tub showers -Attached 2 car garage -FAST WiFi - up to 1 GB -Shuffleboard & arcade game -High chair & pack 'n play

The exterior of the bungalow is highlighted by a charming front porch with a blue door. Vibrant flowers and greenery flourish along the stone landscape, providing a welcoming entrance. Large windows invite natural light into the home, complementing its classic design.

4.97 out of 5 average rating, 123 reviews

Rosie’s Eastside Garden Bungalow

Classic 1920's bungalow 10 minutes from Fiserv Forum, and across from the Oak Leaf trail— Rosie’s is truly a hidden gem on the East Side of Milwaukee. Wake up to birds chirping and enjoy your morning coffee on the air conditioned sun porch. Walk to Collectivo on the Lake, Bradford Beach, UWM, North Avenue, Brady Street, among countless cafes, restaurants, pubs, and more. This is your home away from home with welcoming hosts living next door for any recommendations or questions during your stay.

4.98 out of 5 average rating, 141 reviews

Belleview House: Hot Tub, Fire Table, Fenced Yard

Welcome to Belleview House, a delightful pet-friendly 3-bedroom home nestled in the heart of the vibrant Murray Hill/East Side neighborhood. We have renovated and redecorated the entire home and backyard (November 2025)! ✔ Hot Tub - closed during quiet hours ✔ Fast Wi-Fi ✔ Workspace ✔ Smart TVs ✔ Comfy king, queen, and twin beds ✔ Fenced Backyard with outdoor fire table ✔ Lawn bowling, horseshoe & cornhole ✔ Outdoor dining table ✔ 0.9 mi to Bradford Beach on Lake Michigan ✔ Stocked kitchen

4.99 out of 5 average rating, 147 reviews

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.

Home in Shorewood

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.

4.93 out of 5 average rating, 164 reviews

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.

Home in Shorewood

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.

5.0 out of 5 average rating, 146 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.

An open living area features a modern style with a gray sofa and a wooden coffee table at the center. A dining space with a dark table and chairs is visible to the left, while a staircase leads to the upper level in the background.

4.89 out of 5 average rating, 118 reviews

Cozy 2-bedroom cottage close to everything!

This newly remodeled, cozy cottage has been called a hidden gem. It’s walking distance from Bayshore Mall. Five minute walk to biking/hiking trail, Milwaukee River for fishing and kayaking and Whitefish Bay. Twelve minutes from Lake Michigan, Downtown and the Historic Third Ward! Booking requirements: Full/Complete Air BnB profile. Government ID check for pre-approval and upon arrival. No parties or events. Active noise monitoring device. No pets allowed.

4.96 out of 5 average rating, 169 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, 325 reviews

A spacious living area features a mix of seating options, including a leather couch and armchairs. Large windows allow natural light to brighten the room, highlighting the hardwood floors and area rug. A coffee table sits centrally, providing a functional gathering space.

Apartment in Milwaukee

East Side Home

Upper flat located on Milwaukee's Historic East Side! We hope your stay with us feels like home. Spacious layout for most any kind of group. Stones throw to UWM, Lake Park, and Historic Downer Avenue shopping. Ten minute drive to downtown Milwaukee. We have been so lucky to have great guests, and we are constantly looking to improve your time here. If there is anything you might want for your trip please ask and we will do our best to accommodate.