Holiday Rentals in Milwaukee

2822 available vacation rental offers

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Milwaukee holiday rentals
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Milwaukee holiday rentals: compare the best deals

Best family friendly Milwaukee holiday rentals

Among the 2822 accommodations in Milwaukee, here are the 4 best family friendly rentals

Mid Century Milwaulkee Ryder Cup 2021 - Milwaukee
9.4 11 reviews

Mid Century Milwaulkee Ryder Cup 2021

apartment, River Hills
This Glendale holiday home is conveniently located just a short distance from the Milwaukee River Bike Trail and Lake Michigan, offering easy access to both nature and city amenities. The property consistently receives excellent reviews from guests, highlighting its comfortable and well-equipped nature.
The property has three bedrooms and two bathrooms, comfortably accommodating up to four guests. The home features a fully equipped kitchen, a terrace, a garden, and a spa tub, providing everything you need for a relaxing and enjoyable stay.
Brady St Retreat - Modern And Open Home With Fully Fenced Yard - Milwaukee
10 2 reviews

Brady St Retreat - Modern And Open Home With Fully Fenced Yard

apartment, Milwaukee
This three-bedroom flat is located in Milwaukee's Lower East Side, a short 300-metre walk from Brady Street and within easy reach of the Milwaukee County War Memorial Centre.
This 82 square metre apartment accommodates up to six guests and features a well-equipped kitchen, air conditioning, and parking, with cafes, restaurants, and the Fiserv Forum all nearby.
Bright And Sunny Apartment In Washington Heights - Milwaukee
9.9 67 reviews

Bright And Sunny Apartment In Washington Heights

apartment, Milwaukee
This two-bedroom flat is situated in a diverse neighbourhood with beautiful trees and historic homes, just 8 kilometres from downtown Milwaukee. It has received excellent ratings for location, cleanliness and user experience.
The flat can accommodate up to four guests and offers a spacious, charming layout with high ceilings, built-in shelving and a mix of midcentury and modern decor. Guests can enjoy a well-equipped kitchen, a large front deck with fresh herbs and amazing sunset views, plus a unique "Treehouse" play area perfect for entertaining young children.
Walk To Brady! | Sleeps 12 | 3-story Brew City Gem - Milwaukee
9.8 8 reviews

Walk To Brady! | Sleeps 12 | 3-story Brew City Gem

apartment, Milwaukee
This five-bedroom, two-bathroom duplex on Pulaski Street in Milwaukee is a three-minute walk from Brady Street's amenities and approximately 2.4 kilometres from the Fiserv Forum.
This pet-friendly accommodation sleeps up to 12 guests and includes two kitchens, two living spaces, air conditioning, garden access, and two off-street parking spaces.

Best Milwaukee holiday rentals with parking

A Cozy Modern Get Away - Milwaukee
9.8 11 reviews

A Cozy Modern Get Away

apartment, Milwaukee
This four-bedroom, one-bathroom Milwaukee apartment, ideal for families of up to eight, sleeps eight and offers air conditioning, a kitchen, parking, and internet access; precise location within Milwaukee is unspecified, preventing details on proximity to specific landmarks.
The property boasts excellent user ratings for cleanliness and location, and further information is needed to determine its floor area, layout, and proximity to Milwaukee attractions.
New! Milwaukee Retreat: 7 Bed + Private Backyard - Milwaukee
10 10 reviews

New! Milwaukee Retreat: 7 Bed + Private Backyard

apartment, Milwaukee
This Bay View flat provides a peaceful base, situated a short distance from Milwaukee's key attractions, including the Historic Third Ward (2.9 km), Henry Maier Festival Park (3.5 km), Fiserv Forum (6.6 km), and American Family Field (9.3 km).
This residence accommodates up to 10 guests across 4 bedrooms, featuring a well-equipped kitchen, smart televisions, onsite laundry, high-speed WiFi, and a garden with a firepit and barbecue, ideal for outdoor entertaining.
5 Bedroom Home Milwaukee Eastside - Milwaukee
9.5 49 reviews

5 Bedroom Home Milwaukee Eastside

apartment, Milwaukee
This five-bedroom house is located in Milwaukee's Lower East Side, near Oakland Avenue and North Avenue, within 1.6km of Brady Street, Bradford Beach, and the University of Wisconsin–Milwaukee.
Sleeping up to 11 guests, this recently renovated property boasts a well-equipped kitchen, a living area with a Roku TV, and free street parking (permit required overnight except Saturdays); note that the basement bedrooms share a hallway and the stairs are steep.
Walkable Bay View Upper - Milwaukee
No reviews

Walkable Bay View Upper

apartment, Milwaukee
This Milwaukee flat offers proximity to South Shore Park and Lake Michigan, a 15-minute walk away, and is a 10-minute drive from Downtown.
This upper-level unit accommodates up to four guests, featuring one bedroom, a pull-out sofa, a fully equipped kitchen, and a dedicated workspace, with local amenities like Blackbird Bar and Anodyne Coffee Roasting Co. within walking distance.

Frequently asked questions about holiday rentals in Milwaukee

  • What should a first-time visitor not miss in Milwaukee, WI?

    For a first-time visitor, you should definitely check out the Milwaukee Art Museum, with its iconic Calatrava addition. The Harley-Davidson Museum is a must-see for any motorcycle enthusiast, and a stroll along the lakefront at the Milwaukee RiverWalk is a great way to experience the city's charm.
  • What are the best Airbnb and vacation rentals in Milwaukee?

    Flexhome Brewery District 2br Apt M8, Flexhome Skywalk To Fiserv 1br Apt U6 and Flexhome Brady District 1br Apt E6 are the most popular Airbnb and vacation rentals in Milwaukee among travelers.

  • Which neighborhood in Milwaukee, WI should you consider for a vacation rental?

    The Historic Third Ward is a popular choice, with its trendy shops, restaurants, and art galleries. If you prefer a more residential feel, Bay View offers a mix of Victorian homes, local breweries, and a vibrant nightlife.
  • What are the most popular Airbnbs in Milwaukee?

  • What are the top family-friendly attractions in Milwaukee, WI?

    The Milwaukee County Zoo is a fantastic day out for families, with a wide variety of animals and interactive exhibits. The Discovery World science museum is another great option, offering hands-on learning experiences for all ages.
  • What are the best vacation rentals with a pool in Milwaukee?

  • When is the best time to book a vacation rental in Milwaukee, WI?

    Booking your vacation rental during the shoulder seasons, like spring or autumn, can often mean better deals and fewer crowds. Summer is the busiest time, so book well in advance if you plan to visit during those months.
  • What are the best rentals for families and kids in Milwaukee?

  • What events or festivals should visitors check out in and around Milwaukee, WI?

    The Summerfest music festival in June and July is a major event, showcasing a wide range of musical acts. The Milwaukee Irish Fest in August is also a popular choice, celebrating Irish culture with music, food, and dancing.
  • What are the best rentals or Airbnbs with a jacuzzi in Milwaukee?

  • What are the best budget-friendly activities in Milwaukee, WI?

    A walk or bike ride along the Milwaukee RiverWalk is a great way to enjoy the city's scenery without spending any money. The Public Market is another budget-friendly option, offering a variety of local produce, meats, and cheeses.
  • What are the best restaurants with local dishes in Milwaukee, WI?

    For authentic Wisconsin cuisine, try the Old German Beer Hall, known for its traditional German dishes like bratwurst and sauerbraten. Milwaukee is also home to a thriving food truck scene, with options like The Taco Moto serving up delicious tacos and burritos.
  • What are the best walking or cycling routes in Milwaukee, WI?

    The Oak Leaf Trail is a popular option for walkers and cyclists, offering over 120 kilometres of paved paths along the lakefront and through parks. The Hank Aaron State Trail is another scenic route, following the Milwaukee River through the city.
  • Are there pet-friendly attractions in Milwaukee, WI?

    Yes, many attractions in Milwaukee are pet-friendly. The Milwaukee County Zoo welcomes well-behaved dogs on leashes, and several parks and green spaces are also dog-friendly.
  • What are the benefits of choosing a vacation rental in Milwaukee, WI?

    Vacation rentals offer more space and privacy than hotels, and often come with amenities like kitchens and laundry facilities. They can also be a more affordable option, especially for families or groups.

Popular destinations

Best Milwaukee holiday rentals with a balcony

East Side Studio Apt - Near Brady St And Fiserv With Balcony - Milwaukee
9.4 7 reviews

East Side Studio Apt - Near Brady St And Fiserv With Balcony

studio, Milwaukee
This East Side studio apartment in Milwaukee is conveniently situated near Brady Street and the Fiserv Forum, offering easy access to Marquette University (3.9 kilometres) and UW-Milwaukee (4.2 kilometres).
This 40 square metre studio sleeps up to four guests and features a private balcony, on-site fitness centre, free Wi-Fi, a fully equipped kitchen with a dishwasher, and table tennis, with elevator access for convenience.
Walker`s Point Apt With Gym And Balcony | Sleeps 4-5 - Milwaukee
No reviews

Walker`s Point Apt With Gym And Balcony | Sleeps 4-5

apartment, Milwaukee
This one-bedroom flat is situated in the Walker's Point district of Milwaukee, a 5-minute drive from the historic Third Ward and within walking distance of shops and restaurants.
This 61 square metre flat accommodates up to three guests and features a private balcony, in-unit laundry, a fully equipped kitchen, and access to a 24-hour fitness centre.
Bay View Designer 1br · Best Location With Balcony, Gym, And Terrace · Sleeps 4 - Milwaukee
10 1 review

Bay View Designer 1br · Best Location With Balcony, Gym, And Terrace · Sleeps 4

apartment, Milwaukee
This apartment in Milwaukee's Bay View district is situated less than 1.6 kilometres from downtown Milwaukee and 1.3 kilometres from Fiserv Forum, offering convenient access to the city's attractions.
This well-equipped two-bedroom flat, covering 63 square metres and accommodating up to four guests, features in-unit laundry, a private patio, and access to building amenities including a fitness centre and communal kitchen.
Walker's Point Designer 2br · Prime Location With Balcony And Gym · Sleeps 6 - Milwaukee
8.8 6 reviews

Walker's Point Designer 2br · Prime Location With Balcony And Gym · Sleeps 6

apartment, Milwaukee
This flat is located in Milwaukee's Walkers Point district, offering convenient access to Marquette University (3.4 kilometres) and the University of Wisconsin-Milwaukee (6.4 kilometres), and is close to attractions such as the Eisner Museum, Milwaukee Institute of Art & Design, and Skylight Music Theatre.
This 96 square metre residence accommodates up to 11 guests, featuring two bedrooms, one bathroom, air conditioning, a kitchen equipped with a fridge, microwave, and dishwasher, and a balcony with city views, complemented by an on-site fitness centre and complimentary high-speed WiFi.

Best Milwaukee holiday rentals with air conditioning

Upscale Clean Ranch - Milwaukee
10 1 review

Upscale Clean Ranch

apartment, Glendale
This Glendale property is situated in a peaceful neighbourhood, just 3.2 kilometres from the city centre, with easy access to shopping malls and restaurants. The apartment has consistently received excellent ratings for its cleanliness, location and overall experience.
The four-bedroom home can comfortably accommodate up to ten guests. The property features a private patio with a grill, access to a backyard and front yard, and air conditioning.
Milwaukee Eastside Guest House-1br-updated - Milwaukee
10 56 reviews

Milwaukee Eastside Guest House-1br-updated

house, Milwaukee
This Upper East Side Milwaukee carriage house, situated a short walk from the University of Wisconsin–Milwaukee, Lake Michigan, and Downer Avenue, offers easy access to Milwaukee's downtown area (approximately 4.8km away).
The recently renovated one-bedroom property sleeps two guests and features a modern kitchenette (lacking a stove/oven and dishwasher), high-speed internet, and free on-site parking; nearby attractions include parks, restaurants, and bars.
Stunning Vintage/modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find - Milwaukee
9.7 368 reviews

Stunning Vintage/modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find

apartment, Milwaukee
This holiday home is situated in Milwaukee, just a short distance from the beach, Brady Street, Lake Michigan, and Fiserv Forum. It has received excellent ratings for location, cleanliness, and user experience.
The property offers three bedrooms and two bathrooms, accommodating up to ten guests in a spacious 161 square metre area. Amenities include a swimming pool, spa, garden, terrace, parking, and a fully equipped kitchen with modern appliances.
Remodeled Apartment In Bay View - Milwaukee
9.9 218 reviews

Remodeled Apartment In Bay View

apartment, Milwaukee
This two-bedroom flat is located in Bay View, a short distance from the restaurants, shops and nightlife of the neighbourhood, and is just a few kilometres from downtown Milwaukee, Lake Michigan and the freeway. It has received excellent ratings for its location, cleanliness and overall experience.
The property can accommodate up to five guests and offers a comfortable and stylish interior. It comes with a fully equipped kitchen, air conditioning, parking and contactless keyless entry, as well as access to a range of amenities and attractions.
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