Holiday houses 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.

Gallery House

Welcome to our 1924 Brick Bungalow, The Gallery House! Located in the prestigious Murray Hill Neighborhood, we are a but a 10 min drive North of central downtown Milwaukee. Enjoy easy access to the best neighborhoods; such as Downer Woods, Riverwest, Shorewood, Walkers Point, Bayview, and the Third Ward. We are located 4 blocks from the Milwaukee River, and 1 short mile to the beaches & parks on Lake Michigan. There are grocers, cafe's, a Walgreens, and places to eat in the neighborhood

1 King bed/Close to Downtown Milwaukee/ Free P

Enjoy a fun and relaxing stay in this stylish, cozy, and comfortable vacation rental perfect for couples or solo travelers. Lower Unit in a duplex house, 1 bedroom with a king-size bed 1 bathroom Fully equipped kitchen with a dining table Great coffee room Living room with a home bar and a 55” smart TV (Netflix) Free parking spot Just a 4-minute drive from I94, this home provides easy access to all the city's major attractions, making it the ideal base for exploring the best of Milwaukee.

Shorewood's Sunny Craftsman

Welcome to our beautiful, sun-filled, 2-bedroom flat in the amazing lakeshore community of Shorewood! Fully updated in 2023, this lower duplex unit is on a quiet block, and just two blocks from all the wonderful shops, restaurants, and bars on Oakland Ave. Shorewood is very walkable community, with parks, green spaces, beaches, and beer gardens within walking distance. Take advantage of the fully-stocked kitchen with stainless appliances, including dishwasher. Come visit us today!

Historic Walker’s Point Home • Sleeps 10 • Garage

Welcome to Rosa Luna, a beautifully restored late-1800s cottage in the heart of Walker’s Point. Enjoy vintage charm, original hardwood floors, 3 bedrooms, a spacious skylit attic retreat with 2 double beds, a private fenced backyard, and secure 2-car garage parking. Minutes from downtown, Bay View, restaurants, coffee, nightlife, Summerfest, and sporting events—it’s the perfect home base for your Milwaukee getaway for families or groups of friends.

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.

Cozy Bayview 2BR | Walk to Cafes, Bars, Local Gems

Stay at Bay View Belle, your stylish 2BR in Milwaukee’s beloved Bay View. Walk to cafés, craft breweries, parks, and the lakefront; just 10 minutes to downtown and the airport. Inside: two comfy queen bedrooms 🛏️, a fully stocked kitchen 🍳, fast Wi-Fi, smart TV, and a bright dining/living space for relaxing. Self check-in, free street parking, and a walkable neighborhood—ideal for couples, families, or work trips. Enjoy MKE like a local! ✨

Summerfest Brady St Suite w/ Rooftop Lounge & Gym

Welcome to Keystone on Brady ✨ A stylish city suite in the heart of Brady St—steps to top dining, cafes & nightlife. Enjoy floor-to-ceiling windows, a plush king bed 🛏️ (privacy curtain), Smart TV + workspace 📺, and a fully equipped kitchen 🍳. Unwind on the rooftop BBQ 🔥 or stay active in the fitness center 💪, fast Wi-Fi, and seamless self-check-in 🔐—perfect for elevated city stays, whether weekend or extended.

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.

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.