
Holiday rentals in Milwaukee
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Top-rated holiday rentals in Milwaukee
Guests agree: these stays are highly rated for location, cleanliness and more.

Charming home w/ fire pit, walk to Lake Michigan
Welcome to our home in a quiet neighborhood, a short walk to gorgeous views over Lake Michigan and two blocks to restaurants, shopping, and nightlife. Gather around the fire pit and grill dinner in the back patio. Listen to our vinyl collection or stream your own music while playing board games next to the smart TV. Super-fast internet, a fully equipped kitchen with coffee & tea, and in-unit laundry. Two comfy queen beds + a sleeper sofa. Here with kids? We have toys, a Pack n' Play, & more.

Bay View MKE Hideaway - with Parking!
Cozy, inviting, one bedroom apartment in the heart of Bayview, literally steps away from some of Milwaukee's best restaurants, bars and shops! One of two Airbnb guest spaces in our house, this downstairs apartment is our home base when we're in Milwaukee, and we love sharing it with guests when we’re on the road! We are within five minutes of Summerfest grounds and East Side & Historic Third Ward districts, and within 10 minutes of the airport, downtown, Marquette University, and Miller Park.

WeilHaus: A Cozy Urban Retreat
Welcome to our WeilHaus (we pronouce that "wheel" in Milwaukee). This cozy 2-bed apartment is centrally located on the southern end of Riverwest, close to the East Side, freeways, downtown, parks, bike trails and all the hip neighborhood goodness that Riverwest has to offer you. WeilHaus is one unit in a four-unit building with tons of old-fashioned charm. Enjoy a colorful, stylish retreat, with special books to read, art to enjoy, and thoughtful touches everywhere to help you feel at home.

Nice 1 BR Apt, WIFI & Office, Near State Fair
This beautifully furnished upper duplex offers a cozy and comfortable living space in a safe and peaceful neighborhood. The kitchen comes fully equipped with all the necessary supplies for cooking and dining, and the garage and driveway provide convenient parking options. Stay connected with the included WIFI and watch YouTube TV. Nice Office space. Conveniently located near major freeways, downtown, hospitals, and the State Fair Grounds. Book now for a stress-free and enjoyable stay

Third Ward/King Bed/Free Parking
In the heart of the Third Ward, this newly renovated building has everything you need for your stay. It is located a block from the Public Market, Broadway Street, 3 blocks from Summerfest grounds, and a short walk to all kinds of shopping and restaurants. This 1000 sq foot apartment is on open concept with 1 full bathroom and 1 bedroom with a king bed and large closet. We provide a queen murphy bed in the living room and 2 fold out twin beds. Parking pass must be used at all times.

Funky 2.5BR in the Heart of Bay View - w/ Parking
Perfectly located in Milwaukee’s eclectic Bay View 4 blocks from the lake. Minutes from downtown, summerfest, art museum. You’ll have the entire first floor of this sunny duplex. The space is open concept - 2 bedrooms with Casper mattresses, a bright kitchen with Great Jones cookware, a huge dining room table, office (with an air mattress), and a comfy living room with a 70” smart TV. Step into the fenced-in back yard and chill around the fire pit for optimal hangs.

Historic East Side Duplex, 3BD. No Cleaning Fee!
Minutes from downtown Milwaukee by car or bus, the whole group will enjoy easy access to the city from this central location less than a mile from the UWM campus. A block from the Urban Ecology Center and Oak Leaf Trail access and easy walking distance to North Avenue's restaurants, bars, and the Oriental Theater, there's no shortage of activities, entertainment, and dining options around this historic and charming East Side abode. Or stay in with our grill and fire pit.

1BR Historic Loft • Walkable + Free Parking
Welcome to your stylish Milwaukee retreat! This 1BR loft blends historic Cream City charm with modern comfort. Soaring 15-ft ceilings, exposed brick, and oversized windows create a bright, open space. Enjoy a spacious king bed, fully stocked kitchen, and free off-street parking — rare in this neighborhood. Walk to the Third Ward, Walker’s Point, and Milwaukee’s best restaurants, breweries, shops, and the vibrant riverfront. Perfect for both work and play.

Our Cozy Bay View Bungalow Getaway
Our relaxing, clean, fully equipped Bay View bungalow delivers a perfect getaway. We are equipped with 1g wifi, 4K smart TV, dimmers, and a washer/dryer. Tastefully decorated, uncomplicated, and comfortable. There are cozy coffee shops, restaurants, and local bars just a few blocks from the house. The Bay View Dog Park is one block away. We have parking for two cars. We follow an Enhanced Cleaning Protocol, and are 100% smoke free without exception.

Barclay House in Walker's Point
Our Walker's Point house is recently renovated, nearly everything is new. Relax in this stylish space which includes a private backyard, w/rear & front decks. Located next to cafes and some of Milwaukee's best restaurants. It is also within walking distance to the Summerfest grounds. We are minutes from Downtown Milwaukee, bike trails and the pedal taverns are just a block away from the house. We just recently added a new hot tub!

Historic Lower East Side Apartment with Lake Views
This is one unit in a historical mansion with lake views! Layout is shotgun, open concept with a SMALL functional kitchen. Definitely gives off a pied-à-terre vibe. You have direct access to the back patio and a dedicated parking space around the corner. This unit is in the heart of the lower east side- close to the art museum, cathedral square, Brady st, 3rd ward, as well as the best restaurants and bars in MKE .

*FREE PARKING*Brady Street Private Residence
Welcome to your Milwaukee home-away-from-home! Located just a short stroll from the iconic Brady Street, this spacious and thoughtfully designed unit puts you right in the heart of the city’s energy—boutiques, cafes, restaurants, nightlife, and local flavor are all just steps away Book now and experience Milwaukee like a local—with all the comfort and convenience you need to relax, recharge, and explore.
Popular amenities for Milwaukee holiday rentals
Other great holiday rentals in Milwaukee

Vintage Motel Inspired 1BR City View, Free Parking

Walkable, Clean, Downtown and yet so quiet!

Classy MKE River West -Lower

All the Pleasures of Home

Historic Hawthorne House

Fox Point living near the Lake!

Quiet 1BR Urban Retreat In Fun, Funky Riverwest

Studio apt w/ laundry + parking
When is the best time to visit Milwaukee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $134 SGD | $135 SGD | $147 SGD | $147 SGD | $158 SGD | $179 SGD | $194 SGD | $179 SGD | $154 SGD | $161 SGD | $153 SGD | $153 SGD |
| Avg. temp | -4°C | -3°C | 3°C | 8°C | 14°C | 20°C | 23°C | 22°C | 18°C | 12°C | 5°C | -1°C |
Frequently Asked Questions
What are the best places to stay in Milwaukee?
Visitors frequently choose the Historic Third Ward for warehouse-style lofts and lively markets, while the East Side is known for walkable dining and lakefront access. The Bay View neighborhood is popular for its creative energy and local music venues.
What are the best things to do in Milwaukee with kids?
Families often explore the Milwaukee County Zoo, enjoy interactive exhibits at Discovery World, or wander the Milwaukee Public Museum. Lakefront parks also have play spaces for children to enjoy.
What are some of the best things to do in Milwaukee?
Discover the Harley-Davidson Museum, stroll through the Milwaukee Art Museum, or enjoy the Public Market in the Historic Third Ward. The city’s lakefront trails and riverwalk provide relaxing spaces to unwind.
How is the weather in Milwaukee?
Milwaukee has cold winters, with temperatures often around 17–31°F (−8–−1°C) in January, and mild to warm summers, reaching 65–82°F (18–28°C) in July. Spring and fall bring moderate temperatures and changing lake breezes.
What are the best places to visit in Milwaukee?
The Milwaukee Art Museum’s striking architecture, the Historic Third Ward’s shops, and the Harley-Davidson Museum are frequently suggested highlights. For fresh air, explore the city’s scenic lakefront and botanical gardens.
What are some hiking trails in Milwaukee?
Explore lakeside paths in Veterans Park, wooded trails at Havenwoods State Forest, or take a walk on the Oak Leaf Trail, which loops through natural areas and neighborhoods. These trails are well-suited for both brisk walks and casual strolls.
What are some family activities we can do in Milwaukee?
Families frequently visit Discovery World for hands-on science, tour the Milwaukee Public Museum, or spend time at the Milwaukee County Zoo. Outdoor playgrounds and seasonal lakefront activities also draw visitors with children.
What are some of the best day trip ideas from Milwaukee?
Consider exploring the lakeshore towns known for artisan shops, hiking forests just outside Milwaukee, or historic sites in nearby communities. Many travelers enjoy sunsets along Lake Michigan or excursions to local state parks.
Are there any pet friendly accommodations available in Milwaukee?
Milwaukee has a variety of pet friendly rentals, especially in neighborhoods like Bay View, the East Side, and Walker’s Point. Several parks and river trails make outings with dogs accessible and enjoyable.
What are some local tips for visiting Milwaukee?
Locals suggest dressing in layers due to shifting lake breezes, especially near the waterfront. Sampling local coffee, supporting neighborhood markets, and attending a fish fry are frequent recommendations for an authentic experience.
What is Milwaukee known for?
Milwaukee is known for its brewing heritage, vibrant festivals, and lakefront setting. The city’s museums, longstanding German and Polish culinary influences, and motorcycle culture draw visitors with diverse interests.
What are the best hidden gems to explore in Milwaukee?
Many enjoy exploring Black Cat Alley’s street art murals, smaller galleries in Riverwest, or the tranquil Lynden Sculpture Garden just outside the city. The North Point Lighthouse often attracts those interested in local history and views.
What are the best foods to try in Milwaukee?
Try locally rooted dishes like cheese curds, bratwurst, and frozen custard, along with Friday night fish fry traditions found in many neighborhoods. German-inspired pastries and craft beers are also frequently suggested.
What should I bring for a trip to Milwaukee?
Pack clothing for changing temperatures, including a light jacket even in summer due to lake breezes. Comfortable shoes work well for walking neighborhoods or exploring local parks, and an umbrella can come in handy during spring and autumn showers.
What is the nightlife in Milwaukee like?
Milwaukee has lively venues with live music, comedy, and diverse dance floors, especially in neighborhoods like Walker’s Point and the East Side. Breweries, late-night cafés, and intimate cocktail spots add to the city’s evening atmosphere.
What are the most popular events or festivals in Milwaukee?
Milwaukee’s most popular events include Summerfest in early summer, local ethnic and cultural festivals along the lakefront, and the Wisconsin State Fair in late summer. Seasonal events around major holidays and the Milwaukee Film Festival are also frequently celebrated.
Are there family friendly vacation rentals in Milwaukee?
Milwaukee has many family friendly places to stay, especially in walkable neighborhoods such as the East Side, Bay View, and near the Historic Third Ward. Spaces with multiple bedrooms and access to parks are often available.
When is the best time to visit Milwaukee?
Late spring through early fall is often recommended for warmer temperatures, outdoor events, and lake activities. Autumn has colorful foliage and inviting local festivals, while winter draws those interested in indoor museums or winter sports.
Quick stats about holiday rentals in Milwaukee

Total holiday rentals
Explore 2,300 holiday rentals in Milwaukee

Nightly prices starting at
Milwaukee holiday rentals start at $13 SGD per night before taxes and fees

Verified guest reviews
Over 112,850 verified reviews to help you choose

Family-friendly holiday rentals
1,460 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 790 rentals that welcome pets

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
1,320 properties have a dedicated workspace

Wifi availability
2,260 of Milwaukee holiday rentals include wifi access

Popular amenities for guests
Guests love Self check-in, Gym and BBQ grill across Milwaukee rentals

4.8 Average rating
Milwaukee stays are highly rated by guests – averaging 4.8 out of 5!

Nearby attractions
Milwaukee’s top spots include Milwaukee County Zoo, Harley-Davidson Museum and Milwaukee Art Museum
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- Six Flags Great America
- Alpine Valley Resort
- Kohler-Andrae State Park
- Wilmot Mountain Ski Resort
- Erin Hills Golf Course
- Illinois Beach State Park
- Milwaukee County Zoo
- Bradford Beach
- Milwaukee Public Museum
- Baird Center
- Sunburst
- Discovery World
- Riverside Theater
- Blackwolf Run Golf Course
- Marquette University
- Little Switzerland Ski Area
- Fiserv Forum
- Holy Hill National Shrine of Mary
- Gurnee Mills
- Lake Geneva Cruise Line
- Betty Brinn Children's Museum
- Lake Park
- Lake Geneva Public Library
- South Shore Park




