Holiday homes in Milwaukee

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Top-rated holiday homes in Milwaukee

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Guest favourite

Condo in Bay View

4.99 out of 5 average rating, 174 reviews

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.

11 – 18 Nov

$1,858 AUD total

Guest favourite

Condo in Walker's Point

5.0 out of 5 average rating, 16 reviews

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.

3 – 10 Aug

$8,565 AUD total

Superhost

Condo in Historic Third Ward

4.87 out of 5 average rating, 415 reviews

Luxury 3rd Ward Condo - w/ parking / exec/ family

If you are looking to book for the RNC convention please choose an alternative date and message us. This is a top of the line one bedroom 1000+ sq foot condo in the heart of the Artistic and Posh Third Ward. There are only 31 units in the Atelier building. The space is immaculate and decorated with high end furnishings. This place is perfect for solo business executive in town for a short few weeks (or months) or up to a family of 4 to 6 that wants to experience all of what downtown offers

30 Sept – 7 Oct

$3,894 AUD total

Guest favourite

Condo in Milwaukee

5.0 out of 5 average rating, 97 reviews

Upper East Side, Designer Retreat w/large balcony

In Milwaukee's Historic Water Tower Neighborhood - a bright, open concept, upper flat in a gorgeous 1920's Mediterranean style home. French doors open to a large balcony with lounge chairs & al fresco dining. Featuring a grand living room, galley kitchen, 2 bedrooms & bathroom with walk-in shower! Just steps away from UWM and the city's best restaurants, bars, boutiques & coffee shops on Historic Downer Ave. A few blocks away from Lake Park, the Oak Leaf Trail, Shorewood and Lake Michigan.

10 – 17 Oct

$2,556 AUD total

Guest favourite

Condo in Lower East Side

5.0 out of 5 average rating, 79 reviews

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.

16 – 23 Sept

$3,328 AUD total

Guest favourite

Condo in Milwaukee

4.98 out of 5 average rating, 179 reviews

"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.

20 – 27 Aug

$1,992 AUD total

Guest favourite

Condo in Milwaukee

4.97 out of 5 average rating, 198 reviews

Penthouse Historic Old World 3rd St (Fiserv Forum)

NOTE: If you are looking to book for the RNC convention in July 2024, please message us separately - we have weekly rates available. Spacious and stylish penthouse suite on 5th floor with panoramic views of Historic Old World Third St Entertainment District. Includes 2 bedrooms, 2 full bathrooms, fully equipped kitchen, dining and entertainment area. Centrally located. Just 1-2 blocks from: - Fiserv Forum - Marcus Performing Arts Center - Baird Center - UW Milwaukee Panther Arena

21 – 28 Nov

$5,681 AUD total

Guest favourite

Condo in Milwaukee

4.94 out of 5 average rating, 31 reviews

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.

7 – 14 Dec

$1,648 AUD total

Guest favourite

Condo in Shorewood

4.93 out of 5 average rating, 262 reviews

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.

28 Feb – 7 Mar

$2,591 AUD total

Guest favourite

Condo in Riverwest

5.0 out of 5 average rating, 23 reviews

*New* On the River / 2 KING beds / Free Parking

Welcome to Riverwest Vienna, a 2-bedroom WATERFRONT property located in MKE's Riverwest 'hood. Truly a one of a kind stay. Newly rehabbed space offers modern amenities inc. Tempur-Pedic KING SZ beds + curated design + numerous outdoor spaces. Just pack your bags as unit is stocked with all of the essentials you need. Breweries, coffee shops, restaurants all within walking distance. Central to all inc. Fiserv Forum, Downtown, Lake Michigan all less than 5 miles away.

21 – 28 May

$2,835 AUD total

Guest favourite

Condo in Milwaukee

5.0 out of 5 average rating, 5 reviews

The Beer Baron's Retreat

Enjoy Old Milwaukee hospitality mixed with modern day comforts and kick back with a cold beer reserved just for you. The classic décor of this one bedroom apartment celebrates the luxury lakefront lifestyle of Milwaukee's Beer Barons and Baronesses in the historic Knickerbocker on the Lake. It's a quiet sanctuary with all of the amenities during your stay in Milwaukee. You're centrally located near downtown and just a block from Milwaukee's beautiful lakefront.

11 – 18 Sept

$2,199 AUD total

Guest favourite

Condo in Milwaukee

5.0 out of 5 average rating, 38 reviews

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.

9 – 16 Mar

$4,625 AUD total