Condo holiday rentals in Milwaukee

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.

Dakota Gal Digs | King Sally

Welcome to The Bentley on 6th in beautiful and historic Walker's Point, Milwaukee. You will find yourself in a newly renovated building (Est. 1892) that has 4 separate condos. This listing is our stacked upper and lower condos. Both offer 2 large bedrooms (w/ 2 rollaway twins), 1 bath, a full kitchen, a garage, and a lovely fenced in backyard to enjoy. There are live plants, great vintage pieces, and cozy touches throughout. You will get the city feel while also having peace, quiet and privacy.

Brewers Hill Belle, 2 bed + Loft & balcony

Discover the perfect blend of style and comfort in this expansive top-floor unit! Featuring a sleek open layout, upscale appliances, and a bonus loft—ideal for extra guests or peaceful relaxation. Enjoy the convenience of a private garage and a spacious yard, perfect for gatherings and outdoor fun. Unwind on the balcony while soaking in the charm of historic Brewer’s Hill. Whether you’re walking, biking, riding The Hop, or driving, you’re just minutes away from Milwaukee’s premier attractions!

Riverwest 2BR • Outdoor Oasis • King Beds

Welcome to Riverwest Vienna, a 2-bedroom WATERFRONT condo (UPPER) located in the Riverwest neighborhood. 4 outdoor spaces (SHARED) • Large deck overlooking the Milwaukee river ☀️ • Patio with picnic table ☕ 🍺 • Front porch • Large back lawn Space is newly rehabbed inc. A/C + Tempur-Pedic KING beds + Free Parking + all of the essentials you need Breweries, coffee shops, restaurants all within walking distance. Central to Fiserv Forum, Summerfest, Downtown, Lake Michigan, 3rd Ward, UWM

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.

Full Condo&Garage in Trendy Bay View Milwaukee

This practical and cozy condominium is located in the heart of Bay View right on historic KK Avenue. It is next to the quaint Morgan Park and a bus stop, across the street from Sprocket Cafe, minutes from the lake and walking distance from the greatest trendy shops, bars, restaurants, and other Bay View classics. Whether you are totally new to the Milwaukee scene or just visiting "home", we are glad to welcome you to this charming condo, perfectly placed to meet all your traveling needs.

"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.

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.

Penthouse • Fiserv, Bars, Perks & Big City Views

Spacious, cozy penthouse in the heart of Downtown Milwaukee! Located on vibrant Old World Third Street, you’re steps from historic charm, bars, and dining (including one right in the building). Enjoy a chef’s kitchen, plush bedding, and fast Wi-Fi. We also offer exclusive add-ons—like celebration setups, food & drink packages, and local experiences—to make your stay truly unforgettable. Let us know what you need for a 5-star stay!

Hilltop House - Loft (2nd floor w/ balcony - 05)

Welcome to your home away from home! This charming two-bedroom rental is perfect for couples, families, or small groups looking for a comfortable and convenient stay. Each bedroom is thoughtfully furnished for a restful night’s sleep, and the shared spaces are designed to help you relax and recharge. Located in a prime spot, you'll be just a short distance from local restaurants, shops, and attractions.