Family-friendly holiday rentals 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.

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!

Beautiful Luxury Suite A of Shorewood Home

Our home is perfect for a Milwaukee stay. Full of amenities and great location. This luxury home has two bedrooms, loft bed and two full baths. Large kitchen and dinning area and two living rooms areas. Two of the bedrooms are perfect couple retreats each with a plush king bed. This home has a lot of extra sleeping room if your family is large. Two large sectionals and a queen bed with the most comfortable cotton sheets and down comforters. Ask about parking and backyard patio for grilling.

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.

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

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.

Charming Bungalow Unit Just North of Downtown Milw

Here’s an opportunity that can’t be beat! This fully furnished upper unit in a charming bungalow is ready to be your home base while in Milwaukee. Two bedrooms, one fitted with a king size bed and one with a queen. Full kitchen. Plenty of street parking in this walk able niche neighborhood. Near Downtown, UW-Milwaukee, MSOE, The Milwaukee RiverWalk as well as a quick hop, skip and jump to museums, tours and arenas/stadiums. Easy access to public transportation. No cleaning fees!

Cream City Home - Shorewood

Welcome to our spacious and stylish Airbnb in the heart of Shorewood! This lower unit of a duplex offers two comfortable bedrooms, a fully equipped kitchen, a cozy living room, and a private backyard patio. Our home is located in a quiet and friendly neighborhood, just a short walk away from Lake Michigan and local restaurants and shops. With modern amenities and classic decor, our Airbnb provides a comfortable and convenient home base for your next Wisconsin adventure.

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.

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.

Historic Gem|Steps to UWM|Lake Mich|Free Parking

🔹 5-Star Rated | Superhost Quality | Fast Wi-Fi | Free Parking 🔹 🏡 Experience a Slice of Milwaukee’s History in a 100-Year-Old Home! Step inside this charming first-floor retreat—a beautifully preserved prairie-style home blending historic elegance with modern convenience. Located right across from UWM, this top-rated Airbnb is perfect for visiting students, faculty, families, and travelers looking for a relaxing, walkable neighborhood.

Mid-century Lower in Riverwest

This 2 BR duplex lower apartment is located in Milwaukee's Riverwest neighborhood, 2 miles directly north of downtown. It is furnished with many vintage mid-century furnishings, including a working HiFi. There is a garage space for your use during your stay, and ample street parking right in front making it easy to come and go. The kitchen has dishes, pots, pans, and all the utensils you will need during your time here.