Family-friendly holiday rentals in Milwaukee

Clock Tower Loft Close to Key Attractions

This cozy quiet apt is softly illuminated by the full moon face of the Allen-Bradley Rockwell Clock Tower, a beacon in Milwaukee’s hip and historic Walker’s Point. Relax on the balcony and enjoy garden views plus treats & refreshments. Head out on a stroll or Bublr bike to discover great eats, crafted beers & spirits. Close to: HD Museum, Fiserv Forum, AmFam Field, theaters, museums & the lakefront. Welcome solo adventurers, couples & biz travelers! Easy access to Interstate, Airport & Amtrak.

Belleview House: Hot Tub, Backyard, Fire Table

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

Beautiful Bay View MKE Flat - w/parking!

This is a bright, sunny apartment on the upper level of a sweet little 1870's "Polish Flat" in the heart of Bay View, one of the city's most desirable neighborhoods! We are just steps away from some of Milwaukee's best restaurants, bars, taprooms, boutiques and coffee shops. The space features an efficiency kitchenette, living room, beautiful bedroom and renovated bathroom with walk-in shower! Close to East Side, Walker’s Point, Historic Third Ward, Summerfest, Mitchell Park and the airport.

WeilHaus: A Cozy Urban Retreat

Welcome to our WeilHaus (we pronouce that "wheel" in Milwaukee). This cozy 2-bed apartment is centrally located on the southern end of Riverwest, close to the East Side, freeways, downtown, parks, bike trails and all the hip neighborhood goodness that Riverwest has to offer you. WeilHaus is one unit in a four-unit building with tons of old-fashioned charm. Enjoy a colorful, stylish retreat, with special books to read, art to enjoy, and thoughtful touches everywhere to help you feel at home.

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.

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.

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 .

MKE#205 -Milwaukee's Prize near Fiserv/3rd Ward/DT

Enjoy your new home along historic Wisconsin Avenue; Just 100 feet from the river. Plankinton Clover features wood flooring, stainless steel appliances, quartz counter tops, in-unit washer and dryers, and high ceilings. Community amenities include a fitness center with on-demand workout classes, a club room, skywalk connection, 1 parking space provided, and access to 3rd Street Market Hall!

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.

Brew City Hideaway - Historic Brewers Hill

Built of Cream City brick in 1858, this is truly one of the oldest standing houses in Milwaukee. It’s just one block north of the original Schlitz Brewery and about .8 miles from the Fiserv Forum! The home also has a fenced in yard with a stamped concrete patio which is shared with the other unit on the property. Also, one off-street parking spot.