Holiday 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.

Downtown Oasis: Hot Tub, Garage, 2 King Huge yard!

Bring the whole family to this great place with lots of room for fun. A rock throw away to Milwaukee central featuring the city's best restaurants, bars, shops, and attractions. This exclusive 1800sqft Ranch 3 bedrooms, 9 beds, 2 full and 1 half bathrooms to sleep up to 14 guests. It features everything your family & friends need: Large Kitchen, Wash/Dry, Outdoor Patio, large back yard and a 8 person Hot Tub! Walking to the Fiserv Forum and downtown. Attached Garage w/ Driveway. 1 Gig Internet

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.

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!

Stylish King Bed Retreat in Downtown MKE + 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.

*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.

Luxury 3rd Ward Condo - w/ parking / exec/ family

This is a top of the line one bedroom 1000+ sq foot condo in the heart of the Artistic and Posh Third Ward. There are only 31 units in the Atelier building. The space is immaculate and decorated with high end furnishings. This place is perfect for solo business executive in town for a short few weeks (or months) or up to a family of 4 to 6 that wants to experience all of what downtown offers

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

Amazing view, Modern Space

Soak your cares away in a luxurious 7-person hot tub while taking in breathtaking panoramic views of the Milwaukee skyline! This chic two-level condo, nestled on a hill above the Milwaukee River, puts you just a 10-15 minute stroll away from the vibrant energy of North Ave, Brady St, and downtown—where the action is always happening.