Family-friendly holiday rentals in Milwaukee

Riverwest Vintage Upper

This 3 BR duplex upper apartment in a 2 unit building is located in Milwaukee's Riverwest neighborhood, with queen sized beds in two bedrooms, and also features an office with a futon for additional sleeping and work space. Centrally located just 2 miles north of downtown Milwaukee, this neighborhood is often called the "Brooklyn of Milwaukee". The residents of this neighborhood range from students to professionals. It has a particularly vibrant arts and music scene, and is sought after for its proximity to UW Milwaukee, the Milwaukee River, and downtown. This unit was completely renovated recently, including a completely remodeled kitchen and bathroom, and contains many vintage furnishings. There is a private front entrance for this unit, and there is a garage space and one off-street surface parking space available for your use during your stay. There is also ample street parking available in front of this property. This apartment has a completely open concept layout, the kitchen features granite counter tops and stainless steel appliances, there is a dining area that seats up to 6 people, and there is a large screen TV in the living room. Both bedrooms have queen sized beds. Enjoy cable and WiFi during your stay, or use the vintage stereo to stream music. There is a basement laundry room with free access to a washer and dryer. Spend some time on the private balcony, that is furnished with vintage patio furniture, if weather permits. Although completely updated, this is a two family property that was built at the turn of the twentieth century & the sound barrier is not perfect. You may be able to hear the people or pets in the lower unit or in neighboring properties from time to time, and they may be able to hear you. Thanks for being courteous to the neighbors! Riverwest is diverse, features great coffee shops, restaurants, bars, public transportation, parks, the Milwaukee River Greenway walking and bike trails - all within walking distance or a short drive. This property location is: * 8 blocks from the Brady St. entertainment district * 1 mile from the Oriental Theater - home of the Milwaukee Film Festival - as well as other entertainment options on the East Side. * 2 miles from downtown Milwaukee, Fiserv Forum, etc. * 1.5 miles (6 min by car) from the University of WI - Milwaukee * 1.5 miles from Lake Michigan The kitchen has all you need to cook, and grocery shopping is 3 blocks away. Guest access You will have access to the upper apartment in a 2 unit building, the laundry room in basement, private balcony and 1 parking space in the garage.

Bay View MKE Hideaway - with Parking!

Cozy, inviting, one bedroom apartment in the heart of Bayview, literally steps away from some of Milwaukee's best restaurants, bars and shops! One of two Airbnb guest spaces in our house, this downstairs apartment is our home base when we're in Milwaukee, and we love sharing it with guests when we’re on the road! We are within five minutes of Summerfest grounds and East Side & Historic Third Ward districts, and within 10 minutes of the airport, downtown, Marquette University, and Miller Park.

Vintage Bay View - Big Backyard, Big 1 Bedroom

Welcome to your Milwaukee getaway! Located in the Bay View area, you're walking distance from the best farm-to-table restaurants, music venues, art fairs, and craft beer in the city. Not only that, but Lake Michigan's beaches, Miller Park, and downtown are a short drive away. The location is ideal. The place was created with a 70's midwestern feel, with wood-paneled furniture pieces and mod design. It also boasts a giant kitchen and backyard with grill. We can't wait for you to visit!

Third Ward/King Bed/Free Parking

In the heart of the Third Ward, this newly renovated building has everything you need for your stay. It is located a block from the Public Market, Broadway Street, 3 blocks from Summerfest grounds, and a short walk to all kinds of shopping and restaurants. This 1000 sq foot apartment is on open concept with 1 full bathroom and 1 bedroom with a king bed and large closet. We provide a queen murphy bed in the living room and 2 fold out twin beds. Parking pass must be used at all times.

Bright 1.5BR in the Heart of Bay View - w/ Parking

Perfectly located in Milwaukee’s eclectic Bay View 4 blocks from the lake. Minutes from downtown, Summerfest, art museum, etc. You’ll have the entire second floor of this sunny duplex. The space is open concept - 1 bed with a King Casper mattresses, a bright kitchen with tons of space, a stylish living room with art throughout, and an office (with an air mattress). Fenced-in back yard that's great for pets and chill around the outdoor table for optimal hangs and BBQs.

Tosa Village Studio Apartment

Tosa Village Studio. (Wauwatosa is the first suburb west of Milwaukee). Walk to the Village and explore the boutique shops, restaurants and bars. Enjoy summer concerts in Hart Park. Miller Park (Milwaukee County Stadium - Home of the Brewers) only 3.5 miles away. Close to the Medical Complex, Froedert and Children's Hospitals. 6.5 miles to the Fiserv Forum (Home of the Milwaukee Bucks). Six miles to downtown Milwaukee. Enjoy Summerfest at the Lake Michigan shore.

Bright Corner Loft | King Bed + Free Parking

Welcome to your stylish Milwaukee retreat! This large corner studio loft blends historic Cream City charm with modern comfort. Soaring 15-ft ceilings, exposed brick, and oversized windows create a bright, open space. Enjoy a spacious king bed, fully stocked kitchen, and free off-street parking — rare in this neighborhood. Walk to the Third Ward, Walker’s Point, and Milwaukee’s best restaurants, breweries, shops, and the vibrant riverfront. Perfect for both work and play.

*FREE PARKING*Milwaukee Haven-Modern Central-Brady

Welcome to your Milwaukee home-away-from-home! Located just a short stroll from the iconic Brady Street, this spacious and thoughtfully designed unit puts you right in the heart of the city’s energy—boutiques, cafes, restaurants, nightlife, and local flavor are all just steps away Book now and experience Milwaukee like a local—with all the comfort and convenience you need to relax, recharge, and explore.

Cozy Vibes Apt | City View | Gym | Free Parking

Cream City historical brick building with incredible views of signature landmarks of Walkers Point. Cozily designed space by interior designer to make a romantic getaway or personal solo retreat to concentrate on your higher purpose. Very safe building and walking distance from foodie restaurants, breweries, jazz clubs, and the famed Iron Horse hotel. A perfect getaway for you and yours.

Lakeview Downtown Milwaukee Condo

This charming one bedroom offers a full kitchen, king bed, private full bathroom, dining and living room area. Conveniently located in Milwaukee's East Side - close proximity to lake paths and trails, Juneau park, Brady Street, Fiserv Forum, the Art Museum and Summerfest grounds! Stay here and start your day with a beautiful sunrise in one of the best locations Milwaukee has to offer.

The Dragonfly Loft

The second floor of this house is a spacious private lofted area that is very open and has high Located in the back of home, Private entrance and close to the city. Dogs allowed! Near small bars, stores and short walk to buses that can take you into the city. I live on the lower unit, If you have any questions or request before check-in please message.

Cozy Basement Space In Bay View by Lake Michigan

Our cool, relaxing, newly finished basement apt is located in charming Bay View in Milwaukee. Shared entrance to stair case, but WITH IT'S PRIVATE ENTRANCE this space was designed to give you a great place to stay while you visit Milwaukee. Only minutes away from lake and downtown. ✊🏻✊🏼✊🏽✊🏾✊🏿 BIPOC, LGBTQ+ 🏳️‍🌈 friendly. All are welcome