Milwaukee holiday rentals

We found 1,165 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Milwaukee by choosing from 545 houses, 323 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:22 Jan - 29 Jan

Private kitchen
Living area
Dining
Living area
Exceptional
(14 reviews)

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

Oconomowoc

9% off
S$33,121
for 7 nights, 1 home
S$4,732 per night
includes taxes & fees
Kohl Manor Luxury Lake 8br year round retreat Pool, Cinema, Arcade on LacLaBelle
Living area
Property grounds
Dining
Exterior
Exceptional
(18 reviews)

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

Pewaukee

8% off
S$9,139
for 7 nights, 1 home
S$1,306 per night
includes taxes & fees
Serene 4-bedroom Lake House in Pewaukee-Hot Tub!
Living area
Kitchen. high end appliances. microwave, crock pot, dishes, cooking utensils
Entryway. 2 closets. 1 full bath. access to garage and basement(off limits)
Tree House Fun.  With two swings underneath
Exceptional
(28 reviews)

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

Kenosha

8% off
S$6,739
for 7 nights, 1 home
S$963 per night
includes taxes & fees
Hot tub relaxing retreat. Large group gatherings! Business travel.
Room
The cabin
Outdoor spa tub
Interior
Exceptional
(30 reviews)

Rustic Charm: Pewaukee Lake Cabin, Sauna & Hot Tub

Pewaukee

9% off
S$9,375
for 7 nights, 1 home
S$1,339 per night
includes taxes & fees
Rustic Charm: Pewaukee Lake Cabin, Sauna & Hot Tub
Property grounds
Exterior
Exterior
Private kitchen
Exceptional
(33 reviews)

Magnificently restored, charming, 8+ Bed-Victorian on a beautiful 1.5 acres.

Wales

9% off
S$4,205
for 7 nights, 1 home
S$601 per night
includes taxes & fees
Magnificently restored, charming, 8+ Bed-Victorian on a beautiful 1.5 acres.
Private kitchen
Outdoor dining
Living area
Property grounds
Exceptional
(172 reviews)

4BR House in Glacier Hills County Park / Heart of the Kettle Moraine!

Hubertus

12% off
S$2,653
for 7 nights, 1 home
S$379 per night
includes taxes & fees
4BR House in Glacier Hills County Park / Heart of the Kettle Moraine!
Front living room seating with view to front yard.
Dining room has decorative fireplace, bar cart, and a variety of drinkware.
One of two bedrooms on main level, with two twin XL beds and closet.
Neighborhood coffee roaster 4 blocks away. Try an award-winning Nitro cold brew.
Exceptional
(46 reviews)

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

Milwaukee

11% off
S$7,437
for 7 nights, 1 home
S$1,062 per night
includes taxes & fees
Spacious house, yard, hot tub & games — 1 mile to Downtown and the East Side
Dining
Living area
Room
Living area
Exceptional
(30 reviews)

Walking Distance to Brewer Stadium 3BR, 2BA Gem

Milwaukee

8% off
S$4,868
for 7 nights, 1 home
S$695 per night
includes taxes & fees
Walking Distance to Brewer Stadium 3BR, 2BA Gem
Living area
Private kitchen
Interior
Interior
Exceptional
(24 reviews)

Cottage near Mt. Mary College

Milwaukee

7% off
S$2,716
for 7 nights, 1 cottage
S$388 per night
includes taxes & fees
Cottage near Mt. Mary College
Living area
Terrace/patio
Private kitchen
Dining
Exceptional
(18 reviews)

Milwaukee Bayview Getaway with Private Hot Tub

Milwaukee

7% off
S$5,394
for 7 nights, 1 home
S$771 per night
includes taxes & fees
Milwaukee Bayview Getaway with Private Hot Tub
Dining
Outdoor dining
Exterior
Living area
Exceptional
(6 reviews)

Skyline House on the Hill - Downtown Milwaukee

Milwaukee

7% off
S$6,888
for 7 nights, 1 home
S$984 per night
includes taxes & fees
Skyline House on the Hill - Downtown Milwaukee
Watch people stroll down the main street from the Main Level Living Room
Family / TV Room
Coffee station with drip coffee maker and Keurig.  Includes coffee and K-cups.
Enjoy the summer sunshine on the lawn of Our Happy Place. Grill on the Weber.
Exceptional
(168 reviews)

Our Happy Place in Cedarburg, WI

Cedarburg

8% off
S$2,441
for 7 nights, 1 home
S$349 per night
includes taxes & fees
Our Happy Place in Cedarburg, WI
Interior
Terrace/patio
Interior
Dining
Exceptional
(94 reviews)

Enjoy Beachfront Living With family!

Racine

8% off
S$5,947
for 7 nights, 1 home
S$850 per night
includes taxes & fees
Enjoy Beachfront Living With family!
Interior
Living area
Cedar hot tub
Living area
Exceptional
(9 reviews)

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

Racine

7% off
S$8,223
for 7 nights, 1 home
S$1,175 per night
includes taxes & fees
Nautical Splash Pad, Spacious Home, Private Pool & Cedar Hot Tub.
Your spacious and comfy accommodation waits...
A brand new kitchen, created by a local craftsman awaits.
Dining
Dining
Exceptional
(119 reviews)

Modern, Spacious Home near Cedarburg - Perfect for Families and Girls' Getaways!

Grafton

8% off
S$2,333
for 7 nights, 1 home
S$333 per night
includes taxes & fees
Modern, Spacious Home near Cedarburg - Perfect for Families and Girls' Getaways!
 We eagerly anticipate welcoming you to the entrance of the Bluemound Arcade!
9ft farmhouse style dining table to seat 10 comfortably.
9ft farmhouse style dining table to seat 10 comfortably.
"Spacious entertainment area featuring a pool table, cozy seating with a large TV for streaming, and a stylish dining space. Perfect for relaxing, playing games, or enjoying meals with friends
Exceptional
(44 reviews)

𖤓Blue Storefront 2000sqft Arcade, Pooltable, Foosball, State Fair𖤓

Milwaukee

15% off
S$2,260
for 7 nights, 1 home
S$323 per night
includes taxes & fees
𖤓Blue Storefront 2000sqft Arcade, Pooltable, Foosball, State Fair𖤓
Room
Private kitchen
Exterior detail
Living area
Exceptional
(46 reviews)

3 BR-2Q 2T Beds, 1 bath home walk to State Fair, close to Brewers, & Zoo.

Milwaukee

7% off
S$1,618
for 7 nights, 1 home
S$231 per night
includes taxes & fees
3 BR-2Q 2T Beds, 1 bath home walk to State Fair, close to Brewers, & Zoo.
Private kitchen
Living area
Interior
Room
Exceptional
(14 reviews)

Charming 3-bedroom lake house in serene Richfield!

Hubertus

7% off
S$4,341
for 7 nights, 1 home
S$620 per night
includes taxes & fees
Charming 3-bedroom lake house in serene Richfield!
Room
Terrace/patio
Interior
Private kitchen
Exceptional
(19 reviews)

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

Milwaukee

8% off
S$3,097
for 7 nights, 1 home
S$442 per night
includes taxes & fees
Spacious 3BR/2BA Townhome w/ Private Parking & Walkable East Side
Living Room with 75" Google TV, Queen Size couch pull out bed.
Estabrook park
Bedroom-3. King size bed and 3rd floor balcony.
Bedroom 4: 2 queen beds, 1 queen couch pull out bed.
Exceptional
(28 reviews)

4 Minutes Walk to Lake Michigan Atwater Park Beach Balconies Family Pet Friendly

Milwaukee

8% off
S$2,808
for 7 nights, 1 home
S$401 per night
includes taxes & fees
4 Minutes Walk to Lake Michigan Atwater Park Beach Balconies Family Pet Friendly
Side yard
Harbor and Yacht Club with downtown Racine in the background.
Native garden
Terrace/patio
Exceptional
(50 reviews)

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

Racine

15% off
S$1,764
for 7 nights, 1 home
S$252 per night
includes taxes & fees
Cozy, historic Cream City brick, "Workers Cottage" 2 blocks from Lake Michigan.
Dining
Living area
Interior
Private kitchen
Exceptional
(5 reviews)

Tosa Village Bungalow: Cozy, Charming, Walk to Tosa Village, Parks, and Stores

Milwaukee

7% off
S$2,498
for 7 nights, 1 home
S$357 per night
includes taxes & fees
Tosa Village Bungalow: Cozy, Charming, Walk to Tosa Village, Parks, and Stores
Exterior detail
Dining
Exterior
Living area
Exceptional
(15 reviews)

Family Retreat Near Lake Michigan | Extended Work Stay

Racine

11% off
S$3,634
for 7 nights, 1 home
S$519 per night
includes taxes & fees
Family Retreat Near Lake Michigan | Extended Work Stay
Interior
Living area
Terrace/patio
Interior
Exceptional
(41 reviews)

Newly renovated 3 bedroom home

Franklin

8% off
S$2,842
for 7 nights, 1 home
S$406 per night
includes taxes & fees
Newly renovated 3 bedroom home
  • 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. 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)
  • Crystal Ridge (9.7 mi / 15.6 km)
  • Ray's MTB Indoor Mountain Bike Park (10.3 mi / 16.6 km)
  • Walter Schroeder Aquatic Center (10.5 mi / 16.9 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:

  • Cathedral Square (0.3 mi / 0.4 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)
  • Boerner Botanical Gardens (9.4 mi / 15.2 km)
  • Whitnall Park (10.4 mi / 16.8 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