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Milwaukee Luxury Rentals

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Milwaukee Pet Friendly Vacation Rentals

10.0 (33 Reviews)
House
Perfect Lake House Getaway!
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
10.0 (21 Reviews)
House
Lake and zoo within blocks
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
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Why Choose Rent By Owner for your Milwaukee Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Milwaukee Vacation Rentals

Where are the best neighborhoods to stay in Milwaukee?

Discover the diverse neighborhoods of Milwaukee, Wisconsin, that offer unique experiences for every traveler. Whether you’re seeking vibrant streets filled with cultural attractions or quiet areas with charming local charm, Milwaukee's neighborhoods provide an ideal setting for your stay. Each area presents its own atmosphere, making it easy to find the perfect location for your vacation rentals. Explore neighborhoods that highlight local character and enjoy a seamless booking experience, ensuring your trip to Milwaukee is both memorable and convenient.

Historic Third Ward

This vibrant neighborhood offers a charming blend of historic charm and modern amenities, making it an ideal area to find comfortable vacation rentals near the region's cultural attractions. Staying here puts you close to arts districts and lively galleries.

View 1307+ Rentals in Historic Third Ward

East Town

Located at the heart of the city, this neighborhood provides easy access to downtown Milwaukee and its bustling nightlife, perfect for travelers seeking convenient vacation rentals amidst entertainment and dining options.

View 275+ Rentals in East Town

North Milwaukee

Here, you'll discover a welcoming community with diverse housing options, ideal for those looking to stay in a quieter area while remaining connected to the city’s major attractions and local culture.

View 111+ Rentals in North Milwaukee

Marquette

The Marquette area combines historic architecture with proximity to parks and waterfronts, making it a great choice for travelers searching for scenic vacation rentals in a peaceful setting.

View 1244+ Rentals in Marquette

Maplewood

Known for its friendly atmosphere and green spaces, Maplewood is an excellent destination for visitors looking for cozy vacation rentals in a neighborhood that balances residential comfort with accessibility to the city's highlights.

View 45+ Rentals in Maplewood

Lower East Side

This trendy district offers an eclectic vibe along with numerous dining and entertainment venues, ideal for those seeking vibrant vacation rentals within an energetic neighborhood.

View 149+ Rentals in Lower East Side

Brewers Hill

Famous for its historic breweries and revitalized streets, Brewers Hill provides a unique backdrop for comfortable vacation rentals in a neighborhood rich with local heritage and urban charm.

View 1291+ Rentals in Brewers Hill

Fifth Ward

As an evolving arts and crafts district, this neighborhood presents creative ambiance and boutique accommodations that appeal to travelers interested in exploring Milwaukee's artistic scene.

View 83+ Rentals in Fifth Ward

Best Times to Visit Milwaukee

When should you plan your Vacation Rentals stay?

Choosing the right time to visit ensures you can enjoy the local events and seasonal attractions, making your stay in this destination truly memorable and well-suited to your travel preferences.

Peak Season Highlights

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Summer (June to August)

During the summer months, you can enjoy the warm weather and vibrant city events that draw visitors to this destination. The region experiences its highest tourist influx, making it an ideal time for lively outdoor activities and festivals.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Fall (September to November)

The fall season offers pleasant temperatures and stunning autumn foliage, attracting travelers seeking scenic beauty and cultural events. This period is perfect for exploring the area without the summer crowds.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F

Off-Season Highlights

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Winter (December to February)

In winter, the city takes on a quieter charm with fewer visitors. The cooler weather creates a cozy atmosphere, ideal for enjoying indoor attractions and seasonal festivities in the region.

Average Temperature Daytime: 25°F to 35°F - Nighttime: 15°F to 25°F
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Spring (March to May)

Spring brings milder weather and blooming landscapes, offering a peaceful environment for exploration. Visiting during this off-peak period can provide more relaxed access to the area's sights and local culture.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°F

Weekly Weather Forecast for Milwaukee

How to Book Your Milwaukee Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Milwaukee

More Top-Rated Vacation Rentals in Milwaukee Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy a private outdoor patio or deck to relax and unwind after exploring the city.
  • Take advantage of on-site parking to conveniently come and go during your stay in the region.
  • Make use of a barbecue grill for outdoor dining with family and friends in this destination.
  • Appreciate access to landscaped gardens that add to the scenic charm of your surroundings.
  • Utilize outdoor seating areas designed for socializing and enjoying the fresh air.
  • Benefit from a swimming pool or hot tub to relax outdoors in the area's warm months.
  • Explore nearby parks or green spaces accessible directly from your rental for outdoor activities.

Top Attractions Around Milwaukee

What attractions are nearby?

In this vibrant destination, you can enjoy a variety of activities nearby, including exploring cultural attractions, outdoor recreational spots, and local dining experiences that showcase the best of the region.

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Family Activities

  • Milwaukee County Zoo: Spend a day exploring the diverse animal exhibits and interactive activities at this family-friendly attraction in the area.
  • Discovery World Science and Technology Center: Engage with hands-on exhibits and learn about innovation while enjoying scenic views along the lakefront.
  • Milwaukee Art Museum: Introduce your family to inspiring art collections housed in a stunning architectural setting that captures the essence of this destination’s cultural scene.
  • Lakefront Activities: Take advantage of the beautiful waterfront by biking, picnicking, or enjoying outdoor festivals in the region’s scenic lakeside environment.
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Adult Activities

  • Discover Milwaukee Art Museum: Immerse yourself in the region's rich cultural scene with a visit to this iconic museum showcasing impressive collections and stunning architecture.
  • Explore the Lakefront Trail: Take a scenic walk or bike ride along the lakefront, enjoying picturesque views of Lake Michigan and the vibrant city skyline.
  • Visit the Historic Third Ward: Experience the lively atmosphere of this trendy district filled with boutiques, galleries, and gourmet restaurants perfect for adults seeking local flavor.
  • Enjoy Craft Beer Tours: Sample the region’s renowned brews through guided tours of local breweries, celebrating Milwaukee's reputation as a beer enthusiast's haven.

Other Places to Stay in Milwaukee, WI

Milwaukee County
Milwaukee County Vacation Rentals
Downtown Milwaukee
Downtown Milwaukee Vacation Rentals
East Town
East Town Vacation Rentals
Brady Street
Brady Street Vacation Rentals
Lower East Side
Lower East Side Vacation Rentals
Ozaukee County
Ozaukee County Vacation Rentals
Racine
Racine Vacation Rentals
Historic Downtown Racine
Historic Downtown Racine Vacation Rentals
Westown
Westown Vacation Rentals
Fifth Ward
Fifth Ward Vacation Rentals
Yankee Hill
Yankee Hill Vacation Rentals
Bay View
Bay View Vacation Rentals
More Places to Stay Near Milwaukee

Milwaukee Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining Experiences: Take the opportunity to enjoy authentic regional cuisine at local eateries that highlight the true flavors of this destination.
  • Visit Popular Cultural and Historic Sites: Make time to discover the area’s rich history and vibrant arts scene, enriching your understanding of the region's unique character.
  • Plan Your Transportation in Advance: Utilize public transit or book reliable transportation options to easily navigate the region’s attractions and avoid unnecessary delays.
  • Choose a Central Location for Your Stay: Opt for vacation rentals situated near key points of interest to maximize your convenience and explore more efficiently during your visit.

Transportation Options

  • Milwaukee County Transit System (MCTS): This regional bus network offers convenient routes throughout the area, making it easy for you to explore local attractions without needing a car.
  • Amtrak Hiawatha Service: Connecting here to major cities like Chicago, this rail option provides a comfortable and scenic way to travel between destinations in the region.
  • Rental Car Services: Multiple rental agencies operate near the airport and within the city, giving you flexibility to explore Milwaukee at your own pace from your vacation rental.
  • Bike Share Programs: With several bike-sharing stations scattered across the area, cycling is an eco-friendly and flexible transportation choice during your stay.

Local Customs Options

  • Bratwurst Tradition: You’ll find that enjoying a bratwurst with mustard is a beloved local custom here, reflecting the area's rich German heritage.
  • Brewery Tours: Participating in brewery tours is a popular way to experience the region's long-standing brewing traditions and vibrant craft beer scene.
  • Lakefront Festivals: Attending lakeside festivals and events throughout the summer months allows you to embrace the local culture and enjoy this city’s scenic waterfront.
  • Public Art Appreciation: Exploring the city’s public art installations and murals offers insight into the community’s artistic expression and local history.

Frequently Asked Questions About Milwaukee?

1. What are the top vacation rentals in Milwaukee?

There are a lot of options in Milwaukee. If you plan on staying in the Milwaukee area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Milwaukee:

2. How many vacation rentals have private pools in Milwaukee?

There are 99 vacation rentals with private pools near Milwaukee. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Milwaukee are best for families?

If you are looking for a family-friendly vacation home in Milwaukee, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Milwaukee:

4. How many Rentbyowner vacation rentals are available in Milwaukee?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 2864 in the Milwaukee area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Milwaukee. 

5. What is the cancellation policy for vacation rentals in Milwaukee, Wisconsin?

The cancellation policy varies by listing. You should review the specific terms on each property’s page or contact the owner directly to understand the options available for your booking.

6. Are there any additional fees I should be aware of when booking a rental in this area?

Additional fees such as cleaning fees or service charges are typically detailed in the listing description. Always check the full pricing breakdown before confirming your reservation.

7. How do I ensure that the rental I choose is suitable for my travel needs?

You can find detailed information about amenities, space capacity, and additional features in the property listing. Reaching out to the host can also help clarify any specific requirements you may have.

8. What is the process for checking in and out of vacation rentals here?

Check-in and check-out procedures are specified by each host within the listing. Contact the property owner if you need further instructions or assistance with your arrival or departure.

9. Is there a minimum stay requirement for vacation rentals in this destination?

Minimum stay requirements vary depending on the property. Review the listing details or contact the owner directly to confirm any restrictions before booking.