Condo holiday rentals in Milwaukee

Big 2 bedroom/king beds/Corner Unit/ + parking

This luxury condo is in the heart of downtown Milwaukee close to corporate offices, Theaters, Summerfest grounds, and the convention center. It features 1 king size beds in each room , a pull out queen sofa, 2 twin cots (upon request) and a furnished kitchen, an in unit washer and dryer, and includes a parking spot. We can accommodate up to 8 guests for the night. The included parking is located next door in the parking structure and is a short walk. You will need to park and get the pass first.

Brewers Hill Belle • 2 bed, 2 bath, & balcony

Welcome to your perfect getaway in the heart of Milwaukee! This bright and airy 2nd-floor condo offers 1600 sq ft of stylish, open-concept living—ideal for a relaxing stay with family or friends. The spacious kitchen, cozy living room, and inviting dining area are perfect for unwinding after a day of exploring the city. Step outside onto the private balcony to enjoy the views of the peaceful Brewer’s Hill! Don’t miss the sunlit reading nook, a perfect spot for soaking in the neighborhood vibes.

Bay View - Lake View on the Park w/Secret Lounge

Our 3 bedroom parkside condo in a beautiful historic renovated home is unique, peaceful, and near everything Bay View has to offer. Enjoy views of Lake Michigan from the front porch and dining room. Secret Vintage Lounge downstairs with antiques from all over the world is the perfect unique space - there is nothing else like this in Milwaukee! This 1st floor condo has perfect proximity to South Shore Park on Lake Michigan - Just a minute walk away from South Shore Beach and a lakefront trail.

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.

"Perfect" | Spotless Private Studio Walker's Point

5-star reviews and SuperHost! Immaculately clean and newly renovated studio on an exciting street. Easy self check-in process. INDOOR PARKING INCLUDED A few blocks from the Harley Davidson Museum, Great Lakes Distillery and dozens of MKE's hottest restaurants breweries and night spots. Fast Uber/Lift pick-up. Walk to 3rd Ward and downtown. Bike share just outside the door. Walker's Point is an original settlement that became MKE, cool mix of industry, residential and entertainment.

Relaxing 2-bedroom upper unit close to everything

Quiet, pet-friendly upper unit in a classic Milwaukee Lannon-stone home. Across from a country club and a couple blocks from beautiful Brown Deer Park, this comfy apartment is a wonderful jumping off spot for any Milwaukee visit. We are 15 minutes from the Deer District and downtown Milwaukee, 15 minutes to Miller Park, and 20 minutes to Summerfest grounds. Take a drive to surrounding areas-- 20 minutes to Cedarburg, 25 minutes to Port Washington, and 35 minutes to scenic Holy Hill.

English Tudor - Upper Flat blocks from the beach

Sophisticated 100 Yr Old English Tudor Upper Flat with hardwood floors, crown moldings, sunken living room, natural fireplace, built-in bookcases, and fully furnished. Spacious 2200 sq. foot 2nd-floor unit. Safe and QUIET neighborhood just blocks from Atwater beach. Cats are on the property and do not go any guest space. Make sure you have the correct number of guests on your reservation request. Bookings on a Friday or Saturday are required to include both nights.

Renovated Spacious & Cozy 2BR Unit in ❤️ of MKE

Escape to the perfect destination of Milwaukee. Staying at this spacious home in a safe and peaceful residential neighborhood. Guests will have access to all city's attractions and amenities, while enjoying the peace and privacy of a quiet neighborhood. 5 Min MKE Airport Bayview 8 Min Harley Davidson Museum American Family Stadium (Miller Parkway) Fiserv Forum Milwaukee Art Museum Lakefront/Downtown Summerfest Grounds Discovery World 15 Min MKE County Zoo MKE Mile

Hilltop House - Escape

Your cozy and convenient getaway—just minutes from the heart of the city! This comfortable, thoughtfully designed space is perfect for small groups or families. With a pull-out couch, it sleeps up to 4 guests. This is one of four private units — like a boutique hotel, but way homier and with more amenities. You’ll enjoy a stocked Keurig coffee maker, free WiFi, in-unit laundry, and a full kitchen. Whether you're here for work or play, you'll feel right at home.

Modern Vintage Vibe Condo

Located in the heart of the West Town entertainment district, this condo radiates vintage charm and features views of the Milwaukee River and downtown Milwaukee. We are located across the street from Pere Marquette Park in a thriving entertainment district loaded with restaurants and bars. One block away is the Deer District, which surrounds Fiserv Forum, home to the Bucks, Admirals, and Golden Eagles. The Milwaukee Convention Center is two blocks away.

Downtown Eastside gem near Fiserv Forum Bucks!

2 story loft style. 2 bedrooms. 1 bath. Great views of Milwaukee nestled by the river and near downtown and Fiserv Forum. Enjoy Brady St. Water St. Jefferson St. Milwaukee St. Old World 3rd St. Lakefront. Riverwalk all nearby. Downtown events. Summerfest and other festivals. Grocery stores and restaurants all around. Street Parking is available first come first served basis. Great area for walking. Uber or lyft is available within minutes of ordering.

Spacious Condo, Steps from Fiserv & Restaurants!

Escape to our cozy, spacious retreat in the heart of Downtown Milwaukee. Located on vibrant Old World Third Street, you’re steps from bars, restaurants, and historic charm. Enjoy plush bedding, a full kitchen, fast Wi-Fi, and stylish decor. We also offer exclusive add-ons—like curated food & drink packages or celebration setups—to make your stay extra special. Let us know how we can help create a 5-star experience!