Downtown Milwaukee holiday rentals

We found 303 holiday rentals — enter your dates for availability
Select from 33 houses, 70 apartments and other holiday rentals to find the perfect place for your stay in Downtown Milwaukee. Whether you're staying in a holiday rental with your children and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a hot tub. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Downtown Milwaukee

Showing deals for:1 Jan - 8 Jan

Exterior
Outdoor dining
Interior
Dining
Exceptional
(6 reviews)

Skyline House on the Hill - Downtown Milwaukee

Milwaukee

8% off
AU$10,830
for 7 nights, 1 home
AU$1,547 per night
includes taxes & fees
Skyline House on the Hill - Downtown Milwaukee
Neighborhood coffee roaster 4 blocks away. Try an award-winning Nitro cold brew.
Dining room has decorative fireplace, bar cart, and a variety of drinkware.
Dead Bird Brewery, only 3 blocks away — has vintage arcade games and vegan food.
Front living room seating with view to front yard.
Exceptional
(45 reviews)

Spacious house, yard, hot tub & games — 1 mile to Downtown and the East Side

Milwaukee

11% off
AU$8,127
for 7 nights, 1 home
AU$1,161 per night
includes taxes & fees
Spacious house, yard, hot tub & games — 1 mile to Downtown and the East Side
Living area
Terrace/patio
Dining
Room
Exceptional
(8 reviews)

Brady St Retreat! 4BR House w Patio & Fenced Yard

Milwaukee

6% off
AU$3,080
for 7 nights, 1 home
AU$440 per night
includes taxes & fees
Brady St Retreat! 4BR House w Patio & Fenced Yard
Room
Exterior
Dining
Living area
Exceptional
(34 reviews)

The Gem of Brewers Hill with hot tub and seasonal pool

Milwaukee

7% off
AU$3,015
for 7 nights, 1 home
AU$431 per night
includes taxes & fees
The Gem of Brewers Hill with hot tub and seasonal pool
Lobby
Interior
Private kitchen
Interior
Exceptional
(18 reviews)

Huge condo in historic hotel near Lake Michigan/Parks/Festivals w/parking

Milwaukee

7% off
AU$3,389
for 7 nights, 1 apartment
AU$484 per night
includes taxes & fees
Huge condo in historic hotel near Lake Michigan/Parks/Festivals w/parking
Private kitchen
Terrace/patio
Interior
Room
Exceptional
(17 reviews)

Spacious 3BR/2BA Townhome w/ Private Parking & Walkable East Side

Milwaukee

7% off
AU$3,744
for 7 nights, 1 home
AU$535 per night
includes taxes & fees
Spacious 3BR/2BA Townhome w/ Private Parking & Walkable East Side

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

When is the best time to visit Downtown Milwaukee for a holiday rental?
The ideal time to visit Downtown Milwaukee for a holiday rental is during the vibrant peak season from February to April, with March being particularly popular. This period sees a delightful blend of events and activities, making it an excellent choice for travellers seeking both adventure and cultural experiences.As the winter chill begins to fade, visitors can enjoy the city's beautiful lakeside scenery and participate in outdoor activities, such as walking along the scenic Milwaukee Riverwalk. The milder temperatures, ranging from around -2 to 10 degrees Celsius, create comfortable conditions for sightseeing and exploring the diverse culinary scene that Milwaukee has to offer.If you're looking for a more budget-friendly option, consider visiting in November. This quieter month allows for a leisurely exploration of the city's museums, breweries, and local shops without the hustle and bustle of peak tourist crowds. You can still enjoy the charm of Downtown Milwaukee while taking advantage of lower rental rates.
What are the top attractions in Downtown Milwaukee, Wisconsin, United States of America?
In Downtown Milwaukee, visitors can take part in a variety of attractions that showcase the city's rich culture and history. The Milwaukee Art Museum, with its iconic architecture and extensive collection, is a must-visit and often draws art enthusiasts from all over. Just a short walk away, the Historic Third Ward offers a vibrant arts district filled with boutiques, galleries, and trendy restaurants, making it a superb spot to explore local creativity.Another highlight is the Milwaukee Public Market, located in the Historic Third Ward as well, where you can sample local foods and artisanal products. For those interested in history, the Pabst Mansion provides a glimpse into the city's brewing heritage and is set in a beautiful neighbourhood that reflects Milwaukee's architectural charm.Additionally, the scenic Riverwalk along the Milwaukee River offers an enjoyable stroll with views of the city's skyline and nearby establishments, making it an ideal area for those seeking both leisure and local dining options.
Are all fees included in the Downtown Milwaukee holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Downtown Milwaukee holiday homes with parking?
Stayz offers a wide selection of holiday homes in Downtown Milwaukee with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Downtown Milwaukee holiday homes?
You can find great discounts on holiday homes in Downtown Milwaukee on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Downtown Milwaukee holiday home booking on Stayz?
To find Downtown Milwaukee holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Downtown Milwaukee?
A long-stay holiday home in Downtown Milwaukee is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Downtown Milwaukee holiday home?
Book your Downtown Milwaukee holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Downtown Milwaukee?
Prices for holiday homes in Downtown Milwaukee vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Downtown Milwaukee to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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