Holiday houses in Glendale

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.

Location · Family · Long stay

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.

Location · Family · Walkability

Historic Two Story Bungalow Retreat

This Historic Bungalow Retreat has 4 bedrooms, with its 100 year old charm and modern amenities. Perfectly suited for families or groups, just minutes from downtown and local shopping. The living room has a smart TV, where a beautiful fireplace creates a warm, inviting atmosphere. The dining area seats up to 8 people, while the full kitchen ensures you have everything you need. For some added fun, head to the game room, complete with card table and board games along with arcade gaming machine.

Location · Family · Hospitality

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.

Value · Location · Walkability

Cozy Single-family house

Newly remodeled 2-bedroom house with 2 beds, one bedroom with queen bed and another one is king bed and 2 full bathroom home! Enjoy central air, Wi-Fi, and 1-car driveway parking with additional permit parking on the street . Relax in the cozy living room, cook in the fully-equipped kitchen, or unwind in the private backyard.And relax in the finished basement area. Enjoy the comfort and privacy of having the whole space to yourself, including the backyard. Quiet and nice neighborhood.

Location · Family · Kitchen

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!

Location · Family · Getting around

Little Farmhouse in the City

*The Little Farmhouse in the City is a 1300 sq ft, 2 story home built in 1925 on a 0.7 acre land on northside of Milwaukee in a quiet neighborhood. *It is about a 20 minute drive from downtown Milwaukee, State Fair Grounds, Milwaukee County Zoo, Froedtert Hospital and American Family Field. *It is a place to relax and enjoy the nature in the backyard: garden of vegetables, flowers, fruits, fire pit, picnic table and watch wildlife. **NO PARTIES/EXTRA GUESTS NOT ON RESERVATION**

Location · Family · Cleanliness

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.

Family · Value · Outdoor spaces

Berkeley Bungalow | Blocks from the Lake | Parking

Relax with the whole family just blocks from Lake Michigan in this peaceful Whitefish Bay retreat. Enjoy a bright, stylish home with three spacious bedrooms, two full baths, and a modern kitchen. Walk just 8 minutes to the lakefront and Big Bay Park Beach, or explore nearby cafés, boutiques, and parks on Silver Spring Drive. Only 10 minutes to downtown Milwaukee, museums, lakefront festivals, and the zoo! Comfort, charm, and calm near the water await.

Family · Location · Parking

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.

Location · Family · Walkability

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.

Location · Value · Backyard

The Auburn Place: Cozy 3BR Home in Wauwatosa

Welcome to our charming Wauwatosa home! This 3-bedroom retreat is perfect for families or groups, featuring cozy king bed, an open-concept living area, and a fully equipped kitchen. Enjoy the spacious backyard, ideal for relaxing or barbecuing, and take advantage of the nearby local attractions. Conveniently located near shopping, dining, and parks, this home offers comfort and convenience for your next stay!

Location · Family · Long stay