Milwaukee holiday rentals

We found 1,186 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Milwaukee by choosing from 543 houses, 315 apartments and other holiday rentals. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll have the amenities that you expect and more, including air conditioning and Wi-Fi. No matter what you're looking for, you're sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Milwaukee (and vicinity)

Showing deals for:13 Nov - 20 Nov

Living area
Kitchen. high end appliances. microwave, crock pot, dishes, cooking utensils
Living area
Entryway. 2 closets. 1 full bath. access to garage and basement(off limits)
Exceptional
(25 reviews)

Hot tub relaxing retreat. Large group gatherings! Business travel.

Kenosha

7% off
S$6,999
for 7 nights, 1 home
S$1,000 per night
includes taxes & fees
Hot tub relaxing retreat. Large group gatherings! Business travel.
Private kitchen
Living area
Living area
Dining
Exceptional
(8 reviews)

Kohl Manor Luxury Lake 8br year round retreat Pool, Cinema, Arcade on LacLaBelle

Oconomowoc

9% off
S$33,596
for 7 nights, 1 home
S$4,799 per night
includes taxes & fees
Kohl Manor Luxury Lake 8br year round retreat Pool, Cinema, Arcade on LacLaBelle
Dining
Property grounds
Exterior
Living area
Exceptional
(12 reviews)

Serene 4-bedroom Lake House in Pewaukee-Hot Tub!

Pewaukee

8% off
S$9,623
for 7 nights, 1 home
S$1,375 per night
includes taxes & fees
Serene 4-bedroom Lake House in Pewaukee-Hot Tub!
Living area
Lake
Dining
Living area
Exceptional
(15 reviews)

"Five Bedroom Luxury by the River "

Milwaukee

8% off
S$10,826
for 7 nights, 1 home
S$1,547 per night
includes taxes & fees
"Five Bedroom Luxury by the River "
Living area
Property grounds
Beach
Dining
Exceptional
(78 reviews)

Enjoy Lakefront living with family!

Racine

7% off
S$7,026
for 7 nights, 1 home
S$1,004 per night
includes taxes & fees
Enjoy Lakefront living with family!
Private kitchen
Terrace/patio
Room
Dining
Exceptional
(7 reviews)

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

Milwaukee

6% off
S$2,641
for 7 nights, 1 home
S$377 per night
includes taxes & fees
Brady St Retreat! 4BR House w Patio & Fenced Yard
Enjoy the summer sunshine on the lawn of Our Happy Place. Grill on the Weber.
Family / TV Room
Enjoy sitting under the covered wrap around porch with your favorite beverage.
Coffee station with drip coffee maker and Keurig.  Includes coffee and K-cups.
Exceptional
(162 reviews)

Our Happy Place in Cedarburg, WI

Cedarburg

8% off
S$2,267
for 7 nights, 1 home
S$324 per night
includes taxes & fees
Our Happy Place in Cedarburg, WI
Interior
Terrace/patio
Living area
Interior
Exceptional
(92 reviews)

Enjoy Beachfront Living With family!

Racine

8% off
S$5,814
for 7 nights, 1 home
S$831 per night
includes taxes & fees
Enjoy Beachfront Living With family!
Front porch for relaxing or people watching
Massive living room with Roku-enabled TV, wi-fi, comfy furniture, cozy woodwork
Dining room with beautiful woodwork and antique upright piano
Landing looking down from 2nd floor
Exceptional
(8 reviews)

Huge Historic House Centrally Located in Milwaukee

Milwaukee

8% off
S$3,461
for 7 nights, 1 home
S$494 per night
includes taxes & fees
Huge Historic House Centrally Located in Milwaukee
Interior
Outdoor dining
Room
Private kitchen
Exceptional
(9 reviews)

Gorgeous space with huge porch.

Milwaukee

7% off
S$2,032
for 7 nights, 1 home
S$290 per night
includes taxes & fees
Gorgeous space with huge porch.
Terrace/patio
Harbor and Yacht Club with downtown Racine in the background.
Native garden
Interior
Exceptional
(47 reviews)

Cozy, historic Cream City brick, "Workers Cottage" 2 blocks from Lake Michigan.

Racine

15% off
S$1,612
for 7 nights, 1 home
S$230 per night
includes taxes & fees
Cozy, historic Cream City brick, "Workers Cottage" 2 blocks from Lake Michigan.
Interior
Terrace/patio
Property grounds
Living area
Exceptional
(21 reviews)

Scenic Waterfront Lake Michigan Escape

Racine

7% off
S$3,959
for 7 nights, 1 home
S$566 per night
includes taxes & fees
Scenic Waterfront Lake Michigan Escape
Property grounds
Private kitchen
Living area
Room
Wonderful
(6 reviews)

Quiet Retreat in Morgan Heights, Sleeps 6, 1.5 baths

Milwaukee

17% off
S$1,841
for 7 nights, 1 home
S$263 per night
includes taxes & fees
Quiet Retreat in Morgan Heights, Sleeps 6, 1.5 baths
Interior
Private kitchen
Living area
Room
Exceptional
(22 reviews)

Cottage near Mt. Mary College

Milwaukee

7% off
S$2,295
for 7 nights, 1 cottage
S$328 per night
includes taxes & fees
Cottage near Mt. Mary College
Interior
Living area
Private kitchen
Exterior
Exceptional
(23 reviews)

Green Valley Homes - 2 BDRM Lower Apartment

Milwaukee

7% off
S$1,446
for 7 nights, 1 home
S$207 per night
includes taxes & fees
Green Valley Homes - 2 BDRM Lower Apartment
Private kitchen
Living area
Living area
Dining
Exceptional
(27 reviews)

Oak Park Bliss: 3BR, 2BA Gem

Milwaukee

7% off
S$3,849
for 7 nights, 1 home
S$550 per night
includes taxes & fees
Oak Park Bliss: 3BR, 2BA Gem
Interior
Living area
Dining
Room
Excellent
(22 reviews)

Spacious 4-bedroom home in quiet neighborhood

Milwaukee

8% off
S$1,608
for 7 nights, 1 home
S$230 per night
includes taxes & fees
Spacious 4-bedroom home in quiet neighborhood
Living area
Living area
Interior
Pool
Exceptional
(8 reviews)

Nautical Splash Pad, Spacious Home, Private Pool & Cedar Hot Tub.

Racine

7% off
S$8,030
for 7 nights, 1 home
S$1,147 per night
includes taxes & fees
Nautical Splash Pad, Spacious Home, Private Pool & Cedar Hot Tub.
Sliding Glass Doors leading to Deck.
House in Fall/Winter.
Stairs leading to Master Bedroom and Bedroom Two.
Roku T.V. in Living Room.
Exceptional
(18 reviews)

Whitefish Bay 3Bedroom Entire House Sleeps 4

Milwaukee

15% off
S$2,839
for 7 nights, 1 home
S$406 per night
includes taxes & fees
Whitefish Bay 3Bedroom Entire House Sleeps 4
Stairwell down to first floor in main house.
Lakeside Screen Porch and Great Room of the Main House
Property grounds
Lake is behind the photographer. Screened porch on left. Patio and firepit.
Exceptional
(60 reviews)

Family Retreat, private, large, great for multi-family, company retreat, wedding

Mukwonago

8% off
S$13,225
for 7 nights, 1 home
S$1,889 per night
includes taxes & fees
Family Retreat, private, large, great for multi-family, company retreat, wedding
Exterior detail
Living area
Dining
Private kitchen
Exceptional
(88 reviews)

The Hive 2 Bedroom/2 Bath by Harbor and Root River

Racine

11% off
S$1,624
for 7 nights, 1 home
S$232 per night
includes taxes & fees
The Hive 2 Bedroom/2 Bath by Harbor and Root River
Interior
Living area
Room
Private kitchen
Exceptional
(9 reviews)

Barclay House in Walker's Point

Milwaukee

8% off
S$2,541
for 7 nights, 1 home
S$363 per night
includes taxes & fees
Barclay House in Walker's Point
Terrace/patio
Living area
Private kitchen
Interior
Exceptional
(36 reviews)

Newly renovated 3 bedroom home

Franklin

7% off
S$2,964
for 7 nights, 1 home
S$423 per night
includes taxes & fees
Newly renovated 3 bedroom home
Living room and entry
Dining table
Kitchen
Backyard and parking space
Exceptional
(70 reviews)

Eastside apartment with Private entrance and parking

Milwaukee

14% off
S$1,276
for 7 nights, 1 apartment
S$182 per night
includes taxes & fees
Eastside apartment with Private entrance and parking
  • 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

Head to the arty city of Milwaukee

Come and experience Milwaukee and its museums, art galleries and live music. This city's festivals, theatres and riverfront draw many visitors. Lake Michigan and American Family Field are just a couple of the must-see attractions. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Milwaukee

Are you hoping to discover top things to see and do while you're in the area? Venture out of your cosy holiday rental and experience everything that makes Milwaukee a one-of-a-kind holiday spot. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Henry W. Maier Festival Park (0.7 mi / 1.2 km)
  • Milwaukee Mile Speedway (5.4 mi / 8.7 km)
  • Milwaukee County Zoo (6.8 mi / 10.9 km)
  • Ray's MTB Indoor Mountain Bike Park (10.3 mi / 16.6 km)
  • Walter Schroeder Aquatic Center (10.5 mi / 16.9 km)
  • Milwaukee County Sport Complex (12.3 mi / 19.7 km)

Exploring the natural landscape of Milwaukee

Whether you're looking for adventure or just want to take in the scenery, Milwaukee is a great place to get outside. These are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Lakeshore State Park (0.6 mi / 0.9 km)
  • Veteran's Park (0.6 mi / 0.9 km)
  • Mitchell Park Horticultural Conservatory (2.2 mi / 3.5 km)
  • Bradford Beach (2.3 mi / 3.7 km)
  • Lake Park (2.8 mi / 4.5 km)
  • Boerner Botanical Gardens (9.4 mi / 15.2 km)

Transport options to and around Milwaukee

The nearest airport is in Milwaukee, WI (MKE-General Mitchell Intl.), located 6.3 mi (10.1 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Waukesha, WI (UES-Waukesha County), which is 16.8 mi (27 km) away.

If you prefer to travel by train, Milwaukee Intermodal Station, Milwaukee Airport Station and Sturtevant Station are the main stations that serve the city. Consider catching a ride on the metro at Michigan & Jackson Tram Stop or Clybourn & Jefferson Tram Stop and easily see more of the city.

Frequently asked questions

What is the best area to stay in Milwaukee when booking a holiday rental?
Westown is among the most sought-after neighbourhoods to secure a holiday rental in Milwaukee. While you're here, explore famous attractions such as Fiserv Forum and Riverside Theatre.
What is the most popular type of holiday rental accommodation in Milwaukee?
The most popular types of holiday rentals in Milwaukee are apartments. Prefer something different? Vrbo has a variety of options to match our guests' diverse needs, so you'll see properties in lots of sizes and shapes. The ideal fit is ready and waiting for you — snap up yours today.
How much does it cost to rent a holiday rental in Milwaukee?
Season, length of stay and property type are among the factors that can influence the price of a holiday home. Simply enter your travel dates to find your perfect match. From cosy cabins to expansive luxury villas, all Vrbo holiday rentals provide incredible value.
How much does it cost to rent a beach house in Milwaukee?
The average price for a holiday home near the beach in Milwaukee will depend on when you'll be there and the size and style of property you want. Find prices easily and quickly on Vrbo by entering the dates you'll be travelling. Then use the filters to pick the number of bedrooms and amenities that you prefer, such as air conditioning, WiFi and a pool.
Are there pet-friendly holiday rentals in Milwaukee?
With 405 properties that welcome pets, your furry buddy can join in on your Milwaukee getaway. Use our filter tool to browse our pet-friendly holiday rentals and find a stay that'll set tails wagging on Vrbo.
Can I rent a house with a pool in Milwaukee?
Grab your swimwear and goggles, because there are 56 houses with a private pool in Milwaukee. Unwind at one of these superb holiday rentals and every day can be a pool day. Simply enter your travel dates into Vrbo, then use the "pool" filter to find the perfect place for a splashing good time!
What are popular rental amenities in Milwaukee?
A barbecue grill, a firepit and a nearby river are the most popular rental amenities in Milwaukee. Whether you're taking to the road alone, with a partner or a group of dear friends, Vrbo will help you find a holiday home that fits your style with all the options you need.
Are there large group holiday rentals in Milwaukee?
With 46 properties that can sleep 10 or more people in Milwaukee, there's no need to leave anyone off your guest list. From holidays with the extended family to special events like Christmas and birthday parties, Vrbo can help you find a large group rental to match the occasion.
Are there holiday rentals in Milwaukee that welcome kids?
With 401 family-friendly holiday homes to select from in Milwaukee, now is an awesome time to introduce your little ones to the thrills of travel. Check our "Properties good for families" filter to view stays that feature conveniences perfect for families on the move, such as living rooms, private pools, bunk beds and hot tubs.
What are the top attractions for families in Milwaukee?
Keeping the kids occupied during your holiday in Milwaukee is a cinch with these family-friendly attractions:
  • Harley-Davidson Museum
  • Milwaukee County Zoo
  • Milwaukee Public Museum
Are there one-bedroom holiday rentals in Milwaukee?
Yes, you can pick from 128 one-bedroom rentals in Milwaukee. Whether you'd prefer a townhouse or a condo, our one-bedroom properties are just right if you don't need loads of space. One of the perks of having your own pad? You won't have to share your adventure with strangers.
Can I find two-bedroom holiday rentals in Milwaukee?
Gather your nearest and dearest and enjoy total privacy and comfort in one of the 112 two-bedroom holiday homes Milwaukee has to offer.
Are there holiday rentals with WiFi in Milwaukee?
Whether you want to keep up with the latest news, write a few emails or surf social media, there are 125 holiday homes with WiFi in Milwaukee. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.
How can I find holiday rentals with air conditioning in Milwaukee?
Pick your dates and then make use of the filters to look for holiday rentals with air conditioning in Milwaukee on Vrbo. With 391 air-conditioned properties available here, you can enjoy a cool and comfy stay.
How old do you have to be to rent a holiday rental in Milwaukee?
The minimum age is usually 16, 18 or 21. It can change between properties on Vrbo, so check the rules of your chosen Milwaukee holiday rental before booking your stay.
How long can I rent a holiday rental in Milwaukee for?
It's really down to the Milwaukee property. To view a list of options offering extended stays, just type your travel dates and guest number into the Vrbo search page. You can enjoy having the place to yourself, along with amenities such as a full kitchen, air conditioning and a yard where the kids can run and play. Keep your eyes peeled for long-term stays that offer discounted weekly or monthly prices.

More holiday ideas