Family-friendly vacation rentals in Milwaukee

2BR Sunny Upper in Prime Bay View - w/ Parking

Perfectly located on the main strip of KK in Milwaukee’s eclectic Bay View directly next to bars, restaurants, and shopping. Minutes from downtown, Summerfest, art museum. You’ll have the entire 2nd floor of this sunny duplex. Stylishly designed - 2 bedrooms with Casper mattresses, a bright kitchen with seating area, a work space in the master, and a comfy living room with a smart TV. The space has 2 patio spaces, a small backyard area, an in-unit washer & dryer as well as 1 free parking space.

Spotless, Walkable- Downtown, Fiserv Forum

Conveniently located in Historic Brewers Hill neighborhood. This upper 2 bed/2 bath unit is centrally located to Fiserv Forum, MSOE. Walkable to Lake Front Brewery and restaurants such as Uncle Wolfies and Avli. Fresh Thyme grocery store is just down the hill. 6 min. walk. We also own a 3 bedroom option. The space hosts up to 7 please visit the link to the lower unit. https://www.airbnb.com/rooms/1609061719132973138guests=1&adults=1&s=67&unique_share_id=f8095770-326a-4972-8fa9-5f8c54574f6b

INSTA-worthy 2 Br Downtown Home Sleeps 8 Walkable!

Looking for a fun and vibrant place to stay in Milwaukee? The Pink Lady is the perfect rental for your next girl's weekend, bachelorette party, or birthday celebration. With an open-concept living space, pink kitchen, champagne bar, and private patio, you'll have everything you need for a fun-filled stay. With easy access to top restaurants, breweries, and cultural spots, come experience the best of Milwaukee with us. Book now and immerse yourself in the charm and excitement of Milwaukee!

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.

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.

1BR Historic Loft • Walkable + Free Parking

Welcome to your stylish Milwaukee retreat! This 1BR 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.

The Little Gray House

The Little Gray House is better than ever! This spring we completed many upgrades inside and out - check out our photos! We've got a few small openings left this summer, maybe they work for you? Time to book for fall and winter holidays so you can get in on the best little Airbnb around! The Little Gray House has attained rave reviews from travelers around the world for its comfort, cleanliness, and convenience. Happy to have you!

Brewers Hill Gem w/hot tub & seasonal shared pool

Your family will be close to everything when you stay at this centrally-located place. Walking distance to Brady Street, the Milwaukee River Walk, shops, restaurants and coffee houses. Less than a mile from Fiserv Forum, downtown Milwaukee and just minutes from Bradford Beach. This pet friendly unit has a private fenced in yard, BBQ grill, off street parking for your vehicles and motorcycles, and a hot tub for your use.

Historic Lower East Side Apartment with Lake Views

This is one unit in a historical mansion with lake views! Layout is shotgun, open concept with a SMALL functional kitchen. Definitely gives off a pied-à-terre vibe. You have direct access to the back patio and a dedicated parking space around the corner. This unit is in the heart of the lower east side- close to the art museum, cathedral square, Brady st, 3rd ward, as well as the best restaurants and bars in MKE .

Modern Luxury 1BR Apt with Rooftop+Gym+Parking

Experience Milwaukee like a VIP! This luxury one-bedroom apartment offers the ultimate convenience with direct access to the Fiserv Forum through the building's enclosed skywalk. Whether you're in town for a game, a concert, or simply to explore, you'll love taking in the skyline views from the rooftop patio, working up a sweat in the fitness center, or relaxing in your sleek and comfortable private space.

Downtown-2 King Beds-hot tub-Double Shower-Parking

Discover luxury in historic Brewers Hill, close to all of Milwaukee's main destinations. Newly renovated 3-bed haven with 2 king beds, an 86" TV, and a fully stocked kitchen. Host in style with a dining table for 10. Indulge in 3 bathrooms, featuring a double main shower and a claw tub for a spa-like feeling. Your retreat for modern comfort and historic charm awaits!