Vacation rentals in Milwaukee

Lux Condo | Garage | Fenced Backyard | KING Beds

★Milwaukee's most vibrant neighborhood ★Fenced in backyard ★Free private garage parking ★Free coffee - Free snacks Stay in Milwaukee's most unique suite King George at The Bentley, designed by Peabody's Interiors. Cozy living room, fully equipped kitchen, and two hotel-grade bedrooms set the tone. Spa bath, carrara rain shower, dual vanity, and a wallpapered water closet with a crystal chandelier. King beds, designer bedding, in-unit laundry, private entrance, garage, and a backyard oasis.

Stylish Modern Studio in Vibrant Walker's Point

Discover Milwaukee from our beautifully remodeled light-filled studio, located in the vibrant & trendy Walker’s Point neighborhood. Just steps away from some top local hot spots like the Great Lakes Distillery, Iron Horse, Shaker’s, Fuel Café, Zócalo Food Truck Park, Movida, Var art galleries, Harley-Davidson Museum, Hank Aaron State Trail & much more. Event-goers will appreciate the proximity to all the unique wedding venues & an eclectic mix of bars, restaurants, coffee shops, & vintage shops.

Funky 2BR in Prime Bay View - w/ Parking

Perfectly located on the main strip of KK in MKE's eclectic Bay View directly next to restaurants and bars. Minutes from downtown, Summerfest, art museum. You’ll have the entire first floor of this sunny duplex. Stylishly designed - 2 bedrooms with Casper mattresses, a bright kitchen with seating area, record player, a work space in the master, and a comfy living room with a smart TV. The space has a small backyard area, an in-unit washer & dryer as well as 1 off-street parking space.

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.

Private parking, 5 blocks from South Shore Beach

Experience the Lisbon House: a 1-bedroom retreat in Milwaukee’s vibrant Bay View neighborhood. Inspired by our US-Portugal heritage, this light-filled apartment offers serene Lisbon vibes just 5 blocks from South Shore Beach and Lake Michigan. Walk to local favorites like Axolotl Cafe and The Wiggle Room for the best of MKE food and culture. Whether you’re here for the design or the location, enjoy a curated stay with authentic charm. Your perfect escape starts here!

East Side Living, Brady Street! Off Street parking

Cozy East Side apartment just one block from lively Brady Street—walk to bars, cafés, shops, and Milwaukee’s beautiful lakefront. Bright, clean, and full of vintage charm with modern comforts like AC and smart TVs. Peaceful vibe, not for parties. No Children under 5 since it is an upper apartment. It’s no 5 star hotel, but my cleaners do a deep clean after EVERY rental. I personally love the old charm of this 100 year old building and I hope you will too!

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.

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!

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.