Milwaukee holiday lettings

We found 1,254 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Milwaukee by choosing from 561 houses, 435 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:7 Nov - 14 Nov

Image gallery for Lake Michigan Waterfront Designer Villa

Property grounds
9.8 out of 10 rating
Exceptional
(8 reviews)

Lake Michigan Waterfront Designer Villa

Racine, WI

8% off
Price is £2,561
£366 per night
includes taxes & fees
Lake Michigan Waterfront Designer Villa

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Find out more about Milwaukee

Find out more about Milwaukee

Why visit Milwaukee

  • Scenic Lakeshore: Enjoy picturesque views along Milwaukee's beautiful lakeshore, perfect for leisurely strolls or picnics.
  • Cultural Attractions: Explore a wealth of museums and historic sites that showcase the city's rich heritage and vibrant arts scene.
  • Outdoor Adventures: Benefit from numerous parks and recreational areas ideal for outdoor activities and family outings.
  • Lively Festivals: Experience a variety of local festivals that celebrate culture, music, and food throughout the year.
  • Charming Neighbourhoods: Discover friendly communities with unique shops, eateries, and budget-friendly accommodations.

Popular types of accommodation in Milwaukee

If you're contemplating a getaway to Milwaukee, you'll find a variety of delightful accommodations to suit your needs. Our most sought-after options include houses, cosy apartments, and charming cottages. Whether you're searching for holiday rentals, holiday lettings, or a perfect holiday home, we provide transparency and reassurance in every booking, ensuring a memorable stay in this vibrant city.

  • Houses: The top choice for holidaymakers in Milwaukee, offering spacious and comfortable stays ideal for families or groups.
  • Apartments: A popular option for those seeking a modern and convenient base, perfect for couples or solo travellers.
  • Cottages: Charming and quaint, these rentals provide a cosy retreat for a relaxing getaway.
  • Cabins: Nestled in nature, cabins are a lovely choice for those looking to enjoy the outdoors.
  • Condos: Combining luxury with convenience, condos are perfect for a stylish stay in the city.**

Top attractions in Milwaukee

Milwaukee offers an array of experiences perfect for outdoor enthusiasts, families, and couples alike. With its urban parks, historic colleges, and vibrant event venues, the city is rich in cultural attractions. Visitors can enjoy a variety of activities that cater to those seeking adventure, family fun, or a romantic outing, making it an ideal destination for a memorable holiday.

  • Harley-Davidson Museum: This engaging transport museum showcases the rich history of the iconic motorcycle brand. Visitors can explore fascinating exhibits, enjoy interactive displays, and immerse themselves in the culture of freedom and adventure associated with Harley-Davidson.
  • University of Wisconsin-Milwaukee: A vibrant modern university located in the heart of the city, offering a lively atmosphere. The campus is known for its innovative programs and beautiful lakefront views, making it a hub of academic and social life.
  • Marquette University: A historic institution with stunning architecture and a strong sense of community. The university is steeped in culture, providing visitors with a glimpse into its rich heritage and vibrant student life.

Things to do recommended for couples

For a romantic getaway in Milwaukee, enjoy an evening at The Rave-Eagles Club for live music, bask in the luxury at Pewaukee Lake Beach, or indulge in delightful cuisine at Palermo's Pizza Factory, perfect for couples seeking a warm, inviting atmosphere.

Things to do recommended for families

Families will love the excitement at American Family Field, the fun at Springs Water Park, and the wellness vibes at The Rock Sports Complex. Each venue offers unique experiences for all ages, making Milwaukee a fantastic destination for a memorable family holiday.

Things to do recommended for groups

Explore the vibrant Mayfair Mall for a delightful shopping experience, enjoy a captivating performance at the historic Pabst Theater, or savour local delicacies at the bustling Milwaukee Public Market. These activities promise a fantastic time for your group in Milwaukee.

What do I need to keep in mind when booking a vacation in 'Milwaukee

If you're travelling with a group, family, or pets, or if you're seeking extended stays, it's essential to apply the appropriate filters based on your priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Milwaukee with a group: Think about how many bedrooms you require, as well as any amenities like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all of these options, and much more, on Vrbo.
  • Traveling to Milwaukee with young kids: Planning a trip with young children can be quite demanding. It's important to prioritise their comfort and safety, as well as seek out suitable amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are enjoyable for families.
  • Taking your pets with you to Milwaukee: For many, a family holiday isn’t truly fulfilled without their furry companion by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Milwaukee: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can quickly discover and secure savings on monthly accommodations. Don't forget to include extras like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Milwaukee

Milwaukee is a vibrant metropolis perfect for outdoor adventures, family outings, and romantic retreats. Explore the charming neighbourhoods filled with friendly locals and budget-friendly options. Must-visit destinations include the scenic lakeshore, lively festivals, and engaging museums. Whether you're seeking a family-friendly atmosphere or a romantic getaway, Milwaukee and its surroundings offer the ideal setting for a memorable holiday experience.

  • Downtown Milwaukee: As the vibrant core of Milwaukee, Downtown is a bustling hub where visitors can enjoy family-friendly activities, thrilling sports events, and romantic outings. It's an ideal area for cultural exploration with numerous music concerts and theatrical performances. Notable landmarks include the impressive stadium and sports facilities, as well as a variety of conference venues that host diverse events. Take a leisurely stroll along the Riverwalk, and indulge in the eclectic dining scene that caters to all tastes.
  • Brookfield: Located just outside Milwaukee, Brookfield is a charming city that offers a delightful blend of family-oriented attractions and business amenities. Visitors can enjoy retail therapy at its expansive shopping centres and malls, or partake in the lively atmosphere at the fairgrounds. Brookfield is well-equipped for both leisure and work, making it an excellent choice for those seeking a city-themed experience. The local sports facilities and event venues further enhance its appeal, ensuring there is something for everyone.
  • Racine: Situated along the scenic shores of Lake Michigan, Racine is a picturesque city perfect for outdoor enthusiasts and those in search of romance. The area boasts beautiful recreational spaces and campgrounds, ideal for a day of adventure or relaxation. Visitors can explore the stunning beaches and nearby national parks that offer breathtaking views and a serene escape from the hustle and bustle. Racine's natural beauty makes it a perfect spot for a romantic getaway or a family outing amidst nature.

Best time to go to Milwaukee

If you're planning a trip to Milwaukee, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like January to February and November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January22.1°F (-5.5°C)Light RainMostly CloudyLowSlightly Low
February23.5°F (-4.7°C)No Rain (Dry)Mostly CloudyLowSlightly Low
March34.7°F (1.5°C)Light RainMostly CloudyAverageAverage
April43.7°F (6.5°C)Light RainMostly CloudyAverageSlightly Low
May54.9°F (12.7°C)Light RainMostly SunnyAverageAverage
June64.9°F (18.3°C)Light RainMostly SunnyHighSlightly High
July71.4°F (21.9°C)Light RainMostly SunnyHighSlightly High
August70.7°F (21.5°C)Light RainMostly SunnyHighSlightly High
September64.2°F (17.9°C)Light RainMostly SunnyAverageAverage
October52.0°F (11.1°C)Light RainMostly SunnyAverageAverage
November39.2°F (4.0°C)Light RainMostly SunnyLowAverage
December29.7°F (-1.3°C)Light RainMostly CloudyAverageAverage

Booking with Vrbo is a breeze

Are you aiming to cut costs on your upcoming getaway? It’s worth considering a bit of flexibility with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often results in substantial savings. To discover the perfect Vrbo accommodation that fits your budget, make use of our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board provides you with a dedicated space to plan new journeys, pick up from where you last stopped, or review and organise your travel arrangements. You can easily access properties you’ve saved and booked, now categorised under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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 (5.6 mi / 9 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:

  • Cathedral Square (0.3 mi / 0.4 km)
  • Lakeshore State Park (0.6 mi / 0.9 km)
  • Veteran's Park (0.6 mi / 0.9 km)
  • Riverwalk Plaza (0.6 mi / 1 km)
  • Mitchell Park Horticultural Conservatory (2.2 mi / 3.5 km)
  • Bradford Beach (2.3 mi / 3.7 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?
When considering a holiday rental in Milwaukee, the Historic Third Ward is an excellent choice. This vibrant neighbourhood is renowned for its artistic flair and historic charm, making it a delightful base for your stay. You'll find a lot of galleries, boutiques, and eateries, as well as easy access to attractions like the Milwaukee Art Museum, where the stunning architecture and impressive art collections await. The area also offers the scenic waterfront along Lake Michigan, superb for leisurely strolls or enjoying picturesque views.

Another fantastic option is the East Side, which boasts a lively atmosphere and a youthful energy. This area is well-known for its eclectic mix of shops, trendy cafes, and bars. A visit to the nearby Brady Street will immerse you in a unique blend of local culture, and the stunning views from the Lake Park are not to be missed. There are numerous holiday rentals available in both neighbourhoods, providing a varied selection to suit different preferences and budgets.

For those looking for a more laid-back experience, the Bay View neighbourhood is a hidden gem. This community offers a relaxed vibe with lovely parks and a diverse range of dining options. Top attractions such as the South Shore Park and the charming boutiques along Kinnickinnic Avenue make it an appealing choice for visitors. The range of properties here tends to be ample, suiting those seeking a home away from home in a friendly atmosphere.
How much does it cost to rent a holiday home in Milwaukee?
Prices for holiday rentals in 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Milwaukee to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Milwaukee holiday house rentals?
You can find great discounts on house rentals in Milwaukee on Vrbo, 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.
Where are the best areas for renting a beach house in Milwaukee?
For renting a beach house in Milwaukee, the area along Lake Michigan offers some delightful options. The neighbourhood of Bradford Beach is particularly popular, known for its sandy shores and vibrant atmosphere. Here, you'll find beach houses that often come equipped with amenities such as outdoor patios, barbecues, and beach gear, superb for enjoying sunny days by the water.

Moving further south, the area around South Shore Park presents a more tranquil setting with picturesque views of the lake. Rentals in this vicinity typically feature spacious living areas and kitchens, ideal for families or groups looking to cook and relax after a day spent by the beach. Many properties also provide access to private decks or gardens that overlook the water, enhancing the overall experience.
What is the most popular type of holiday rental accomodation in Milwaukee?
In Milwaukee, holiday houses are the most popular type of rental accommodation, with around 427 available throughout the city. These properties are often found in varied neighbourhoods, allowing guests easy access to local attractions such as the Milwaukee Art Museum and the Historic Third Ward. Most holiday houses come equipped with multiple bedrooms, full kitchens, and spacious living areas, making them ideal for families or groups.
Are there any family house rentals in Milwaukee?
In Milwaukee, there are numerous family-friendly holiday rentals available—approximately 398 options scattered throughout the city. Neighbourhoods like Bay View and the Historic Third Ward are particularly appealing for families. In Bay View, visitors can find spacious homes with large living areas, fully equipped kitchens, and outdoor spaces great for children to play. These properties often have amenities such as Wi-Fi and laundry facilities, ensuring a comfortable stay for families.

Meanwhile, the Historic Third Ward offers a vibrant atmosphere with easy access to local attractions like the Milwaukee Public Market and the scenic waterfront. Here, families can discover apartments and townhouses that feature modern conveniences, including ample dining spaces and sometimes even balconies with lovely views of the city.
Can I rent a holiday home with a pool or hot tub in Milwaukee?
In Milwaukee, there are plenty of holiday homes available for rent that feature pools or hot tubs, with approximately 82 options to choose from. This vibrant city offers various neighbourhoods where these properties can be found, including the historic Third Ward, known for its chic boutiques and dining, and the serene Lake Park area, which provides a more residential feel.
Can I find long-stay holiday rentals in Milwaukee?
A long-stay holiday rental in 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Milwaukee?
In Milwaukee, there are numerous pet-friendly house rentals available, with over 300 options for travellers to choose from. Many of these properties are located in vibrant neighbourhoods such as the Historic Third Ward and Bay View, where visitors can enjoy a blend of culture and community. Holiday rentals in these areas typically come with amenities like spacious backyards, fully equipped kitchens, and comfortable living spaces, making them ideal for families and groups travelling with pets.

The Historic Third Ward is particularly appealing, featuring a mix of modern and historic architecture, alongside trendy shops, restaurants, and galleries. Nearby, the Milwaukee RiverWalk offers scenic views and walking paths, great for leisurely strolls with pets.
Are there any remote work holiday rentals in Milwaukee?
In Milwaukee, there are numerous remote work holiday rentals available, with around 745 options for travellers seeking a conducive work environment. The city offers a variety of properties that cater to remote workers, especially in neighbourhoods such as the Historic Third Ward and Bay View, both known for their vibrant atmospheres and proximity to local amenities.

Many of these rentals are equipped with essential features for productivity, including high-speed Wi-Fi, dedicated desk spaces, and comfortable office furniture like desk chairs and monitors, ensuring that guests can work efficiently. Additionally, some properties may offer business centre access and secure safe storage for valuables, enhancing the overall convenience for professionals. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Milwaukee holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in 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 on Vrbo 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.
What are popular rental amenities in Milwaukee?
In Milwaukee, popular rental amenities primarily include free in-room Wi-Fi, kitchens equipped with essential appliances such as refrigerators and microwaves, as well as cookware, dishware, and utensils for preparing meals. These amenities enhance the comfort and convenience of stays, making it easier for travellers to enjoy home-cooked meals and stay connected during their visit.
When is the best time to visit Milwaukee for a holiday rental?
The best time to visit Milwaukee for a holiday rental is during the vibrant summer months of May to July, with July being particularly popular among travellers. This period is characterised by warm temperatures, often reaching the low 30s Celsius, making it ideal for outdoor activities and sightseeing. Milwaukee comes alive with festivals, outdoor concerts, and a bustling atmosphere that invites exploration of its beautiful waterfront and historic districts.

If you enjoy a lively environment filled with cultural events, July is the month for you. The city hosts numerous summer festivals, including the renowned Summerfest, which attracts music lovers from all over. The pleasant weather encourages visitors to engage in activities like cycling along the lakefront or enjoying a leisurely stroll through the Milwaukee Art Museum's stunning architecture.

For those looking for a more budget-friendly experience, consider visiting in December. While it's a quieter time in terms of tourist activity, the festive holiday lights and winter markets create a charming atmosphere that showcases a different side of Milwaukee. This month offers a unique opportunity to explore the city's rich German heritage through its Christmas celebrations, all while enjoying the local cuisine in a cozy setting.
How early should I book a Milwaukee holiday rental?
Book your Milwaukee holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Milwaukee?
In Milwaukee, visitors can discover a variety of attractions spread across its vibrant neighbourhoods. The Historic Third Ward is known for its artsy vibe, featuring the Milwaukee Art Museum with its stunning architecture and the bustling Milwaukee Public Market, where you can sample local delicacies. Holiday rentals in this area often reflect the creative spirit and provide easy access to the waterfront.

In the East Side, you'll find a lively atmosphere with numerous bars, restaurants, and the scenic Lakefront Trail, superb for those who enjoy outdoor activities. Properties here may offer a blend of modern amenities and historic charm, making it an appealing choice for travellers.

The Bay View neighbourhood is another great option, known for its energetic shops and community feel. Here, holiday homes can be found close to parks such as South Shore Park, which offers beautiful views of Lake Michigan and access to recreational activities.
Can I change or cancel my Milwaukee home rental booking on Vrbo?
To find Milwaukee holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Milwaukee holiday rental prices shown on Vrbo?
Vrbo 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.

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