Downtown Milwaukee holiday rentals
We found 352 holiday rentals — enter your dates for availability
Select from 32 houses, 92 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:28 Nov - 5 Dec
Image gallery for Lake Drive Mansion ~ Downtown ~ Art Museum ~ Lakefront
1010 out of 10 rating
Exceptional
(10 reviews)
Lake Drive Mansion ~ Downtown ~ Art Museum ~ Lakefront
Milwaukee, WI
7% off
Price is S$10,710
S$10,710
S$1,530 nightly
Includes taxes & fees
Image gallery for 4 bd Victorian, close to downtown, great for groups and family gatherings
1010 out of 10 rating
Exceptional
(14 reviews)
4 bd Victorian, close to downtown, great for groups and family gatherings
Milwaukee, WI
8% off
Price is S$5,629
S$5,629
S$804 nightly
Includes taxes & fees
Image gallery for Spacious house, yard, hot tub & games — 1 mile to Downtown and the East Side
1010 out of 10 rating
Exceptional
(37 reviews)
Spacious house, yard, hot tub & games — 1 mile to Downtown and the East Side
Milwaukee, WI
15% off
Price is S$6,110
S$6,110
S$873 nightly
Includes taxes & fees
Image gallery for 3Kings, Renovated, FenceYard, Games, Ctr Loc - WEEKLY STAY DEALS
1010 out of 10 rating
Exceptional
(13 reviews)
3Kings, Renovated, FenceYard, Games, Ctr Loc - WEEKLY STAY DEALS
Milwaukee, WI
22% off
Price is S$2,165
S$2,165
S$309 nightly
Includes taxes & fees
Image gallery for The Gem of Brewers Hill with hot tub and seasonal pool
9.89.8 out of 10 rating
Exceptional
(18 reviews)
The Gem of Brewers Hill with hot tub and seasonal pool
Milwaukee, WI
11% off
Price is S$2,578
S$2,578
S$368 nightly
Includes taxes & fees
Image gallery for Brady St Home with a Private Outdoor Bar and Deck!
1010 out of 10 rating
Exceptional
(8 reviews)
Brady St Home with a Private Outdoor Bar and Deck!
Milwaukee, WI
11% off
Price is S$10,564
S$10,564
S$1,509 nightly
Includes taxes & fees
Image gallery for Brady St. Retreat - Where Families & Groups Gather
1010 out of 10 rating
Exceptional
(7 reviews)
Brady St. Retreat - Where Families & Groups Gather
Milwaukee, WI
7% off
Price is S$5,446
S$5,446
S$778 nightly
Includes taxes & fees
Image gallery for Brady St - Secret Garden - Fire Pit - Chic Victorian - Family Friendly
9.89.8 out of 10 rating
Exceptional
(16 reviews)
Brady St - Secret Garden - Fire Pit - Chic Victorian - Family Friendly
Milwaukee, WI
7% off
Price is S$3,220
S$3,220
S$460 nightly
Includes taxes & fees
Image gallery for Downtown home w/ rooftop patio - walk everywhere!
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Downtown home w/ rooftop patio - walk everywhere!
Milwaukee, WI
20% off
Price is S$6,259
S$6,259
S$894 nightly
Includes taxes & fees
Image gallery for Best location in Milwaukee! Upper Duplex Unit - long term stays welcome
8.68.6 out of 10 rating
Excellent
(22 reviews)
Best location in Milwaukee! Upper Duplex Unit - long term stays welcome
Milwaukee, WI
7% off
Price is S$1,454
S$1,454
S$208 nightly
Includes taxes & fees
Image gallery for Style and Luxury - Unbeatable Location
9.69.6 out of 10 rating
Exceptional
(10 reviews)
Style and Luxury - Unbeatable Location
Milwaukee, WI
7% off
Price is S$3,014
S$3,014
S$431 nightly
Includes taxes & fees
Image gallery for Brady St. Inn and Gallery
9.89.8 out of 10 rating
Exceptional
(28 reviews)
Brady St. Inn and Gallery
Milwaukee, WI
8% off
Price is S$5,303
S$5,303
S$758 nightly
Includes taxes & fees
Image gallery for Lower East Side - 3 bed, 2 bathroom, 2 private parking spots
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Lower East Side - 3 bed, 2 bathroom, 2 private parking spots
Milwaukee, WI
7% off
Price is S$3,164
S$3,164
S$452 nightly
Includes taxes & fees
Image gallery for Comfort Near Historic Pabst Brewery & Fiserv
9.29.2 out of 10 rating
Wonderful
(12 reviews)
Comfort Near Historic Pabst Brewery & Fiserv
Milwaukee, WI
8% off
Price is S$1,915
S$1,915
S$274 nightly
Includes taxes & fees
Image gallery for Cream City Lounge Parking AC Patio Pets Sleeps 11
1010 out of 10 rating
Exceptional
(16 reviews)
Cream City Lounge Parking AC Patio Pets Sleeps 11
Milwaukee, WI
7% off
Price is S$3,561
S$3,561
S$509 nightly
Includes taxes & fees
Image gallery for Large Luxury Home - Perfect for Groups - Downtown
1010 out of 10 rating
Exceptional
(37 reviews)
Large Luxury Home - Perfect for Groups - Downtown
Milwaukee, WI
8% off
Price is S$6,352
S$6,352
S$907 nightly
Includes taxes & fees
Image gallery for Chic Milwaukee Studio, Walk to Beach & Brady St Eats
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Chic Milwaukee Studio, Walk to Beach & Brady St Eats
Milwaukee, WI
8% off
Price is S$1,114
S$1,114
S$159 nightly
Includes taxes & fees
Image gallery for Large Lower East Side MKE flat (sleeps 10) near Brady Street & N Water Street
9.69.6 out of 10 rating
Exceptional
(15 reviews)
Large Lower East Side MKE flat (sleeps 10) near Brady Street & N Water Street
Milwaukee, WI
11% off
Price is S$2,843
S$2,843
S$406 nightly
Includes taxes & fees
Image gallery for Spacious Walkers Point Gem in Central Milwaukee
9.69.6 out of 10 rating
Exceptional
(23 reviews)
Spacious Walkers Point Gem in Central Milwaukee
Milwaukee, WI
7% off
Price is S$4,334
S$4,334
S$619 nightly
Includes taxes & fees
Image gallery for Milwaukee 1BR Bungalow with free parking
8.68.6 out of 10 rating
Excellent
(29 reviews)
Milwaukee 1BR Bungalow with free parking
Milwaukee, WI
8% off
Price is S$1,280
S$1,280
S$183 nightly
Includes taxes & fees
Image gallery for Kasa | Family Friendly Westown 2BD + Amenity Access | Milwaukee
8.88.8 out of 10 rating
Excellent
(6 reviews)
Kasa | Family Friendly Westown 2BD + Amenity Access | Milwaukee
Milwaukee, WI
8% off
Price is S$3,372
S$3,372
S$482 nightly
Includes taxes & fees
Image gallery for Tucked Away Off Brady - 4 Beds
9.09.0 out of 10 rating
Wonderful
(18 reviews)
Tucked Away Off Brady - 4 Beds
Milwaukee, WI
14% off
Price is S$1,838
S$1,838
S$263 nightly
Includes taxes & fees
Image gallery for Eastside apartment with Private entrance and parking
9.69.6 out of 10 rating
Exceptional
(63 reviews)
Eastside apartment with Private entrance and parking
Milwaukee, WI
14% off
Price is S$949
S$949
S$136 nightly
Includes taxes & fees
Image gallery for Stunning Upscale Retreat - Steps From Everything
9.89.8 out of 10 rating
Exceptional
(28 reviews)
Stunning Upscale Retreat - Steps From Everything
Milwaukee, WI
7% off
Price is S$3,055
S$3,055
S$436 nightly
Includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find properties near top attractions in Downtown Milwaukee
Map Attractions
Find the best place to stay - Downtown Milwaukee
The Plaza Hotel
Sleeps 4 · 1 bedroom
8.88.8 out of 10
Excellentexcellent
1,124 reviews(1,124 reviews)
Downtown Eastside gem near Fiserv Forum Water St Brady St
Sleeps 4 · 2 bedrooms · 1 bathroom
9.29.2 out of 10
Wonderfulwonderful
41 reviews(41 reviews)
Luxury Penthouse, Best Location, Free Parking
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
22 reviews(22 reviews)
Cozy 4 Bedroom on Popular Historic Brady St
Sleeps 8 · 4 bedrooms · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
6 reviews(6 reviews)
Luxury Historic Home - Stellar Location
Sleeps 8 · 3 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
23 reviews(23 reviews)
Cozy 2 Bedroom Downtown Milwaukee Apartment
Sleeps 4 · 2 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of holiday rental accommodation in Downtown Milwaukee?
The most desirable types of holiday rentals in Downtown Milwaukee are apartments. Want something different? Vrbo has plenty of options to match our guests' unique requirements, so you'll see properties in all shapes and sizes. The perfect fit is ready and waiting for you — get yours today.
How much does it cost to rent a holiday rental in Downtown Milwaukee?
The average price for a holiday home in Downtown Milwaukee is based on several factors, such as property type, length of stay and season. Whether you'd like a sprawling villa with space for the whole family or an apartment perfect for just you and the kids, just add your dates of travel to discover some great-value stays.
How much does it cost to rent a beach house in Downtown Milwaukee?
The average price for a holiday rental close to the beach in Downtown Milwaukee depends on when you're going and the size and style of property you want. Find prices easily on Vrbo by entering your destination and travel dates. Then use our filter tool to select the number of bedrooms and amenities important to you, like WiFi, air conditioning and a pool.
Are there pet-friendly holiday rentals in Downtown Milwaukee?
Pack a suitcase and a bone for the pup in your life because Downtown Milwaukee has 70 holiday rentals that throw out the welcome mat to pets. Let your furriest pal enjoy fun with the family at one of our pet-friendly holiday rentals on Vrbo. Simply enter your dates and destination, then check our "Pets allowed" filter box.
Can I rent a house with a pool in Downtown Milwaukee?
Check the "pool" box in our handy filter tool and pick from nine houses with private pools in Downtown Milwaukee on Vrbo. Morning dip, sunset soak or midnight swim? Free time is up to you when your Vrbo holiday property boasts a swimming pool.
What are popular rental amenities in Downtown Milwaukee?
A fireplace, a nearby waterfront and nearby museums head the list of most popular rental amenities in Downtown Milwaukee. Whether you're heading away on your own, with a partner or a group of dear friends, Vrbo can help you find a holiday rental that fits your tastes with a load of extras you'll love.
Are there large group holiday rentals in Downtown Milwaukee?
With four properties that can sleep 10 people or more in Downtown Milwaukee, there's no need to leave anyone off your guest list. From holidays with the extended family to events like weddings and birthday parties, Vrbo can help you find a large group rental to suit the occasion.
Are there holiday rentals in Downtown Milwaukee that welcome kids?
Gather the whole crew for the adventure of a lifetime in Downtown Milwaukee at one of our 70 family-friendly holiday rentals. A lot of these stays offer amenities that are great for getaways with the kids, like laundry facilities, extra bedrooms and entertainment areas. Simply check the "Properties good for families" filter and choose your favourite.
What are the top attractions for families in Downtown Milwaukee?
There are plenty of fun things to see and do with the family in Downtown Milwaukee, including:
- Harley-Davidson Museum
- Milwaukee County Zoo
- Milwaukee Public Museum
Are there one-bedroom holiday rentals in Downtown Milwaukee?
Yes, you can take your pick from 34 one-bedroom rentals in Downtown Milwaukee. Whether you'd like a townhouse or an upmarket condo, Vrbo's one-bedroom properties are perfect if you don't need a lot of space. One of the main perks of having your own place? You'll never need to share your adventure with strangers.
Can I find two-bedroom holiday rentals in Downtown Milwaukee?
Gather your nearest and dearest and relax in total privacy and comfort in one of the 20 two-bedroom holiday properties Downtown Milwaukee has to offer.
Are there holiday rentals with WiFi in Downtown Milwaukee?
Downtown Milwaukee has 11 holiday rentals with WiFi, so you can stay connected while travelling. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming movie blockbusters to sending emails, these Vrbo homes make it a cinch to get online.
How can I find holiday rentals with air conditioning in Downtown Milwaukee?
You can choose from 68 holiday homes with air conditioning in Downtown Milwaukee offering that cool, cool breeze and extra bit of comfort. Enter your preferred dates of travel and then take advantage of our filter tool to find properties with air conditioning.
How old do you have to be to rent a holiday rental in Downtown Milwaukee?
The minimum age is usually 16, 18 or 21. It can differ between properties on Vrbo, so look at the rules of your preferred Downtown Milwaukee holiday home before you book.
How long can I rent a holiday rental in Downtown Milwaukee for?
The amount of time you can rent a Downtown Milwaukee holiday rental for is up to each property. Simply tap in your travel dates to view options offering longer term stays. They have everything you need to make your extended break more enjoyable like kitchens and backyards. Some properties might also offer discounted weekly or monthly prices, so you can stick around for longer for less.