Holiday houses in Milwaukee

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Top-rated holiday rentals in Milwaukee

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A spacious living area features a cozy tufted sofa adorned with decorative pillows, complemented by a circular glass coffee table. A vibrant area rug with floral patterns enhances the warm wood floors. Colorful artwork decorates the walls, adding a playful touch to the room.
Home in Bay View
4.92 out of 5 average rating, 132 reviews

2BR Sunny Upper in Prime Bay View - w/ Parking

Perfectly located on the main strip of KK in Milwaukee’s eclectic Bay View directly next to bars, restaurants, and shopping. Minutes from downtown, Summerfest, art museum. You’ll have the entire 2nd floor of this sunny duplex. Stylishly designed - 2 bedrooms with Casper mattresses, a bright kitchen with seating area, a work space in the master, and a comfy living room with a smart TV. The space has 2 patio spaces, a small backyard area, an in-unit washer & dryer as well as 1 free parking space.

Guest favourite
An open concept kitchen features a large white island with seating, accompanied by modern cabinetry. The living space extends into a bright dining area, enhanced by natural light from a window. Decorative artwork and a wall clock add character to the surroundings.
Home in Halyard Park
4.94 out of 5 average rating, 158 reviews

Downtown Oasis: Hot Tub, Garage, 2 King Huge yard!

Bring the whole family to this great place with lots of room for fun. A rock throw away to Milwaukee central featuring the city's best restaurants, bars, shops, and attractions. This exclusive 1800sqft Ranch 3 bedrooms, 9 beds, 2 full and 1 half bathrooms to sleep up to 14 guests. It features everything your family & friends need: Large Kitchen, Wash/Dry, Outdoor Patio, large back yard and a 8 person Hot Tub! Walking to the Fiserv Forum and downtown. Attached Garage w/ Driveway. 1 Gig Internet

Top Guest favourite
A vibrant living room features a yellow sofa adorned with colorful throw pillows, paired with unique armchairs. A large mural in bold colors occupies one wall. Natural light filters through sheer curtains, illuminating plants and decorative shelves, creating an inviting atmosphere.
Home in Walker's Point
4.99 out of 5 average rating, 191 reviews

INSTA-worthy 2 Br Downtown Home Sleeps 8 Walkable!

Looking for a fun and vibrant place to stay in Milwaukee? The Pink Lady is the perfect rental for your next girl's weekend, bachelorette party, or birthday celebration. With an open-concept living space, pink kitchen, champagne bar, and private patio, you'll have everything you need for a fun-filled stay. With easy access to top restaurants, breweries, and cultural spots, come experience the best of Milwaukee with us. Book now and immerse yourself in the charm and excitement of Milwaukee!

Guest favourite
A spacious living room features a vintage-inspired green velvet sectional sofa paired with plush pillows. A glass coffee table rests on a soft area rug, with natural sunlight illuminating the room. Decorative plants and a round mirror add to the inviting atmosphere.
Apartment in Bay View
4.95 out of 5 average rating, 845 reviews

Beautiful Bay View MKE Flat - w/parking!

This is a bright, sunny apartment on the upper level of a sweet little 1870's "Polish Flat" in the heart of Bay View, one of the city's most desirable neighborhoods! We are just steps away from some of Milwaukee's best restaurants, bars, taprooms, boutiques and coffee shops. The space features an efficiency kitchenette, living room, beautiful bedroom and renovated bathroom with walk-in shower! Close to East Side, Walker’s Point, Historic Third Ward, Summerfest, Mitchell Park and the airport.

Top Guest favourite
A cozy living area features a soft sofa adorned with colorful cushions, complemented by an accent chair. A stylish glass coffee table sits atop a geometric-patterned rug. Natural light filters through two windows, enhancing the warm ambiance of the space.
Townhouse in Bay View
4.95 out of 5 average rating, 448 reviews

Vintage Bay View - Big Backyard, Big 1 Bedroom

Welcome to your Milwaukee getaway! Located in the Bay View area, you're walking distance from the best farm-to-table restaurants, music venues, art fairs, and craft beer in the city. Not only that, but Lake Michigan's beaches, Miller Park, and downtown are a short drive away. The location is ideal. The place was created with a 70's midwestern feel, with wood-paneled furniture pieces and mod design. It also boasts a giant kitchen and backyard with grill. We can't wait for you to visit!

Guest favourite
An intimate living area features a comfortable sofa adorned with decorative pillows, paired with a wooden dining table. An open kitchen area with sleek cabinetry is visible in the background. Six tall windows allow natural light to brighten the space, with a patterned rug underfoot.
Condo in Historic Third Ward
4.93 out of 5 average rating, 184 reviews

Third Ward - High End 1 Bedroom up to 6 + Parking

This is a top of the line one bedroom 1000+ sq foot condo in the heart of the Artistic and Posh Third Ward. There are only 31 units in the Atelier building. The space is immaculate and decorated with high end furnishings. This place is perfect for solo business executive in town for a short few weeks (or months) or up to a family of 4 to 6 that wants to experience all of what downtown offers. This building is next to local restaurants, The Hop Street Car, and the Public Market.

Top Guest favourite
An open-concept living area features a blue sofa and an armchair beside a small wooden table. A patterned area rug anchors the seating space. Large windows allow natural light to fill the room, highlighting the modern kitchen appliances in the background.
Apartment in Historic Third Ward
4.95 out of 5 average rating, 199 reviews

Stylish King Bed Retreat in Downtown MKE + Parking

Practical conveniences are included to make your stay seamless. Included off-site parking is available nearby, and detailed instructions will be provided before your arrival. High-speed WiFi, secure floors through fob access, and self check-in ensure the experience is smooth and stress-free. The building itself reflects Milwaukee’s industrial roots while offering the safety and comfort that modern travelers expect.

Guest favourite
A modern living space features a sectional sofa with plush pillows, paired with a stylish coffee table. The area is complemented by a dining set and a fully equipped kitchen in the background. Large windows provide natural light, illuminating the artwork on the walls.
Apartment in Milwaukee
4.82 out of 5 average rating, 286 reviews

MKE#249 -Milwaukee's Favorite near Fiserv/3rd Ward

Enjoy your new home along historic Wisconsin Avenue; Just 100 feet from the river. Plankinton Clover features wood flooring, stainless steel appliances, quartz counter tops, in-unit washer and dryers, high ceilings, over-sized windows. Community amenities include a fitness center with on-demand workout classes, a club room, skywalk connection, ample parking, and access to 3rd Street Market Hall!

Top Guest favourite
The bright living area features tall, arched windows allowing natural light to fill the space. A spacious sectional sofa is adorned with various textured throw pillows, while a colorful area rug anchors a wooden coffee table. Decorative plants and wall art enhance the airy atmosphere.
Apartment in Walker's Point
4.98 out of 5 average rating, 208 reviews

Cozy Vibes Apt | City View | Gym | Free Parking

Cream City historical brick building with incredible views of signature landmarks of Walkers Point. Cozily designed space by interior designer to make a romantic getaway or personal solo retreat to concentrate on your higher purpose. Very safe building and walking distance from foodie restaurants, breweries, jazz clubs, and the famed Iron Horse hotel. A perfect getaway for you and yours.

Guest favourite
The entrance features a charming facade with three large windows and a decorative door. A set of stairs leads up to the front door, flanked by a wrought-iron railing. Lush greenery surrounds the base, enhancing the welcoming appearance of the home.
Loft in Riverwest
4.87 out of 5 average rating, 623 reviews

The Dragonfly Loft

The second floor of this house is a spacious private lofted area that is very open and has high Located in the back of home, Private entrance and close to the city. Dogs allowed! Near small bars, stores and short walk to buses that can take you into the city. I live on the lower unit, If you have any questions or request before check-in please message.

Guest favourite
A spacious living area features a comfortable sectional sofa and a mounted flat-screen TV. Natural light floods through multiple windows, revealing views of the city skyline. A cozy gas fireplace adds warmth, while a dining area can be seen in the background.
Townhouse in Riverwest
4.92 out of 5 average rating, 257 reviews

Amazing view, Modern Space

Soak your cares away in a luxurious 7-person hot tub while taking in breathtaking panoramic views of the Milwaukee skyline! This chic two-level condo, nestled on a hill above the Milwaukee River, puts you just a 10-15 minute stroll away from the vibrant energy of North Ave, Brady St, and downtown—where the action is always happening.

Top Guest favourite
The living area features two dark leather sofas arranged around a low coffee table, set on an area rug with a decorative pattern. Natural light filters through the window coverings, and a floor lamp provides additional illumination.
Apartment in West Allis
4.96 out of 5 average rating, 233 reviews

Clean 1bd/1bath close to everything!

Charming 1 bedroom 1 bath with private entrance and parking. Close to downtown, Shopping malls, Zoo, Hospital, Airport,Main freeways. Full kitchen with stove, microwave, coffee pot, dishes. Unit has tv and wifi. Coin operated laundry is accessible on premis. Why stay at a hotel when you can feel at home in this lovely unit.

Popular amenities for Milwaukee holiday rentals

When is the best time to visit Milwaukee?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$185 NZD$187 NZD$203 NZD$203 NZD$218 NZD$247 NZD$268 NZD$247 NZD$213 NZD$211 NZD$201 NZD$196 NZD
Avg. temp-4°C-3°C3°C8°C14°C20°C23°C22°C18°C12°C5°C-1°C

Frequently Asked Questions

  • How is the weather in Milwaukee?

    Milwaukee has a humid continental climate with hot, humid summers and cold, snowy winters. Summer temperatures range from 70°F (21°C) to 80°F (27°C), while winter can drop to 20°F (-6°C) with frequent snowfall, providing opportunities for winter activities like ice skating and snowshoeing.

  • What are some of the best things to do in Milwaukee?

    Explore the Milwaukee Art Museum, take a leisurely stroll along the Lakefront Trail, and engage with science at the Discovery World. Learn about Harley-Davidson motorcycles at the Harley-Davidson Museum, or enjoy the beauty of nature at the Mitchell Park Horticultural Conservatory.

  • What is the best time of year to visit Milwaukee?

    Many travelers visit Milwaukee between June and September when the weather is warm, around 70°F (21°C) to 80°F (27°C). The city hosts several events during this time, including Summerfest, one of the world's largest music festivals, and the Wisconsin State Fair in August.

  • What are the best places to stay in Milwaukee?

    East Town is popular for its nightlife and dining options, while the Historic Third Ward is known for its converted warehouses and boutiques. Bay View has a strong community vibe and Walker's Point is a revitalizing neighborhood with a growing food scene.

  • What are the best places to visit in Milwaukee?

    Frequently suggested places include the Milwaukee Public Museum, the historic Pabst Mansion, and the Milwaukee County Zoo. For nature lovers, Bradford Beach and the Boerner Botanical Gardens are often recommended.

  • What are some hiking trails in Milwaukee?

    The Oak Leaf Trail is a 125 miles (200 km) greenway that encircles Milwaukee County. Grant Park Trails offers a more challenging hike with beautiful views. The Seven Bridges Trail in Grant Park is also a popular option, known for its scenic surroundings.

  • What are some family activities to do in Milwaukee?

    Families can have a fun day at the Betty Brinn Children's Museum, learn about aquatic life at the Milwaukee County Zoo, or explore the natural beauty of Lake Park. The Milwaukee Public Museum is also great for families with its interactive exhibits.

  • What are some of the best day trip ideas in Milwaukee?

    Travelers can take a day trip to Madison, Wisconsin's capital, or visit the Kettle Moraine State Forest for outdoor activities. The charming town of Cedarburg, known for its well-preserved 19th-century buildings, is another option worth considering.

  • What types of vacation rentals are available in Milwaukee?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Milwaukee. From over 810 apartment rentals to over 1,120 house rentals, we've got you covered.

  • Are there vacation rentals with a dedicated workspace in Milwaukee?

    Yes! Work meets play with ease at over 1,320 vacation rentals in Milwaukee featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Milwaukee?

    Four-legged friends are welcome in Milwaukee. Choose from more than 770 vacation rentals for guests traveling with pets.

  • Are there Milwaukee vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Milwaukee, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in guesthouse rentals in Milwaukee?

    Experience the best of Milwaukee with our guesthouse rentals, starting at about $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there family-friendly vacation rentals in Milwaukee?

    Milwaukee has more than 1,440 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do hotel rentals in Milwaukee have a gym?

    Absolutely! We offer over 10 hotel rentals with a gym in Milwaukee. Enjoy a tailored experience with all the comforts you desire.

  • Do bungalow rentals in Milwaukee have a bbq area?

    Absolutely! We offer over 10 bungalow rentals with a bbq area in Milwaukee. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Milwaukee have self check-in?

    Absolutely! We offer over 30 condo rentals with self check-in in Milwaukee. Enjoy a tailored experience with all the comforts you desire.

  • Do private suite rentals in Milwaukee have wifi?

    Absolutely! We offer over 20 private suite rentals with wifi in Milwaukee. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Milwaukee

  • Total holiday rentals

    Explore 2,310 holiday rentals in Milwaukee

  • Nightly prices starting at

    Milwaukee holiday rentals start at $18 NZD per night before taxes and fees

  • Verified guest reviews

    Over 112,600 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,440 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 770 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    1,320 properties have a dedicated workspace

  • Wi-Fi availability

    2,270 of Milwaukee holiday rentals include Wi-Fi 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

Destinations to explore

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