Milwaukee holiday lettings

We found 1,323 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Milwaukee by choosing from 526 houses, 498 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:10 Oct - 17 Oct
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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.

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.

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

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.

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?
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.

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