Family-friendly vacation rentals in 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

Stylish Bay View Guest House, Walk to Bars+Dining

Our Guest House (700 sq ft) is perfect for families & groups seeking a modern space within walking distance to some of the best restaurants, bars, breweries & cafes in Milwaukee's popular Bayview neighborhood. Enjoy your stay in comfort with 2 bedrooms & 3 total beds (3 queens). Our Guest House is located directly behind the Main House on the same lot (separate houses). Street parking is available right outside our house with plenty of spots typically available.

Our Cozy Bay View Bungalow Getaway

Our relaxing, clean, fully equipped Bay View bungalow delivers a perfect getaway. We are equipped with 1g wifi, 4K smart TV, dimmers, and a washer/dryer. Tastefully decorated, uncomplicated, and comfortable. There are cozy coffee shops, restaurants, and local bars just a few blocks from the house. The Bay View Dog Park is one block away. We have parking for two cars. We follow an Enhanced Cleaning Protocol, and are 100% smoke free without exception.

Swan City Cozy Boho in Bay View

Welcome to Swan City located in the heart of Bay View. With beautiful hardwood floors and a cozy boho-inspired decor, our space is designed to make you feel right at home from the moment you arrive. Centrally located, we are within walking distance of several restaurants, bars, and co-ops. This community is known for its lively atmosphere and friendly locals, and there's always something exciting to see, or an event to attend in the neighborhood.

The Little Gray House

Summer time in the 414! We've got a few small openings left this summer, maybe they work for you? Time to start thinking about booking for fall and winter so you can get in on the best little Airbnb around! All the home upgrades are done, and we'l be posting photos within the next couple of weeks. The Little Gray House has attained rave reviews from travelers around the world for its comfort, cleanliness, and convenience. Happy to have you!

Barclay House in Walker's Point

Our Walker's Point house is recently renovated, nearly everything is new. Relax in this stylish space which includes a private backyard, w/rear & front decks. Located next to cafes and some of Milwaukee's best restaurants. It is also within walking distance to the Summerfest grounds. We are minutes from Downtown Milwaukee, bike trails and the pedal taverns are just a block away from the house. We just recently added a new hot tub!

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 .

King Bed Retreat with MKE Views + Parking

Practical conveniences are included to make your stay seamless. Included off-site parking is available nearby, and detailed instructions will be provided before your arrival. High-speed WiFi, secure floors through fob access, and self check-in ensure the experience is smooth and stress-free. The building itself reflects Milwaukee’s industrial roots while offering the safety and comfort that modern travelers expect.

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.

The Peacock Place w/ Shared Seasonal Outdoor Pool

This 3 bedroom, 1 bath, open concept lower unit of a duplex is located in Brewer's Hill. This unit has tons of natural light, original hard wood floors, pocket doors and claw foot soaking tub. This pet friendly unit has off street parking for 2 vehicles or motorcycles, and a private yard with patio and BBQ grill for your use. Walking distance to Brady Street, downtown and Fiserv Forum.

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.

Bremen Street House | Lower Flat

Milwaukee has a unique architectural style called “Polish Flats,” which mostly reside in the Riverwest neighborhood. Located east of the Milwaukee River, we’re blocks from the Oak Leaf bike trail. A selection of independent coffee shops and roasters, restaurants, bars, and breweries are within easy walking distance.