Holiday houses in Milwaukee

Brady St Apartment with Parking

You’re one block off Brady Street—Milwaukee’s most vibrant strip of bars, restaurants, coffee shops, and local boutiques. * Free shuttles to Summerfest, Brewers, and Bucks games pick up just around the corner * Walk to cafes like Nomad or Rochambo for a slow morning coffee * Pharmacy, groceries, and essentials all within a block Head a few blocks east and you’ll hit the lakefront—perfect for a morning run, bike ride on the Oak Leaf Trail, or relaxing by the marina, beach, or Veteran’s Park.

Private East Side Milwaukee flat with fenced yard

Enjoy the best that the East Side and downtown have to offer in this second floor standalone home on the Oak Leaf Trail with no shared walls, private fenced-in yard with spacious deck and patio, and private parking lot. This historic cream city brick building was constructed in 1897 and completely renovated in 2017 with custom features throughout. Gas fireplace, 70" TV in living room with custom hi-fi built-in stereo system, tons of natural light. Double guest suites with amenities galore.

Charming Bungalow Unit Just North of Downtown Milw

Here’s an opportunity that can’t be beat! This fully furnished upper unit in a charming bungalow is ready to be your home base while in Milwaukee. Two bedrooms, one fitted with a king size bed and one with a queen. Full kitchen. Plenty of street parking in this walk able niche neighborhood. Near Downtown, UW-Milwaukee, MSOE, The Milwaukee RiverWalk as well as a quick hop, skip and jump to museums, tours and arenas/stadiums. Easy access to public transportation. No cleaning fees!

Bright & Quiet 2BR | Parking | Airport & Bay View

Every room is thoughtfully renovated with a nod to 70s-inspired design. New kitchen, refreshed bathroom, freshly painted bedrooms, and a redesigned living room. No detail was overlooked. Curl up with a book on the sofa, put on a movie, or enjoy a quiet evening in a space that’s cozy, stylish, quiet and completely your own. Whether you’re passing through or staying a few days — we’ve got you covered. Fast WiFi, driveway parking, and just a 5 minute drive to the airport and Bay View.

Oliver's Traveler Oasis

Welcome to Oliver’s Traveler Oasis—a cozy, sunny 2BR retreat in Wauwatosa. Walk to coffee, parks, and restaurants, or drive 10 min to downtown MKE. You're also minutes away from AmFam Field and Froedtert. Enjoy a full kitchen, comfortable living and dining area, smart TV, shared backyard, gym, and laundry. We’re a friendly, active family downstairs with two sweet kids under 3. Perfect for couples, families, or work trips. Come relax, explore, and feel right at home!

Lower East Side, Modern Updates, Fenced Yard

Welcome to our charming home in the heart of MKE’s Lower East Side just steps from lively Brady Street. Tucked on a side street, this retreat is the perfect home base for exploring. Inside, you’ll find a bright, spacious living area and a well-equipped kitchen. Whether you’re visiting with family, friends, or for business, you’ll love being a short walk from MKE's best cafes, restaurants, bars and shops. Enjoy the energy of the East Side with all the comforts of home.

Brady St Suite • Free Parking • Rooftop & Gym •

Welcome to Keystone on Brady ✨ A stylish city suite in the heart of Brady St—steps to top dining, cafes & nightlife. Enjoy the large 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 💪. Includes FREE secure indoor parking 🚗, fast Wi-Fi, and seamless self-check-in 🔐—perfect for elevated city stays, whether weekend or extended.

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! ✨

Historic Gem|Steps to UWM|Lake Mich|Free Parking

🔹 5-Star Rated | Superhost Quality | Fast Wi-Fi | Free Parking 🔹 🏡 Experience a Slice of Milwaukee’s History in a 100-Year-Old Home! Step inside this charming first-floor retreat—a beautifully preserved prairie-style home blending historic elegance with modern convenience. Located right across from UWM, this top-rated Airbnb is perfect for visiting students, faculty, families, and travelers looking for a relaxing, walkable neighborhood.

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.