Best Vacation Homes in Milwaukee County
1600 ft²
12 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $501/Night
For 7 Nights US $3,508
1130.21 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Apartment
- Air Conditioner
- Internet
- Child Friendly
US $276/Night
For 7 Nights US $1,932
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $218/Night
For 7 Nights US $1,527
1200 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Condo
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $345/Night
For 7 Nights US $2,412
1506.95 ft²
8 Guests
3 Bedrooms
3 Bathrooms
House
- Hot Tub
- Balcony/Terrace
- Kitchen
US $264/Night
For 7 Nights US $1,851
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $275/Night
For 7 Nights US $1,927
1033 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $176/Night
For 7 Nights US $1,231
1033 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $159/Night
For 7 Nights US $1,114
Milwaukee County Luxury Rentals
20 Guests
1 Bedroom
3 Bathrooms
Free Cancellation
House
- View
- Parking
- Air Conditioner
US $2,651/Night
For 7 Nights US $18,557
2840 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Kitchen
- Air Conditioner
- Internet
US $2,205/Night
For 7 Nights US $15,437
10763.91 ft²
16 Guests
6 Bedrooms
3 Bathrooms
House
- Fireplace/Heating
- View
- Pet Friendly
US $2,166/Night
For 7 Nights US $15,162
29 Guests
9 Bedrooms
4 Bathrooms
Pet Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $1,919/Night
For 7 Nights US $13,433
16 Guests
6 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $1,738/Night
For 7 Nights US $12,163
2497.23 ft²
16 Guests
4 Bedrooms
3 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Parking
- Air Conditioner
US $1,677/Night
For 7 Nights US $11,739
4766 ft²
30 Guests
6 Bedrooms
5 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $1,649/Night
For 7 Nights US $11,546
12 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $1,532/Night
For 7 Nights US $10,727
Milwaukee County Pet Friendly Vacation Rentals
4 Guests
2 Bedrooms
1 Bathroom
Couples Retreat
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $115/Night
For 7 Nights US $804
538.2 ft²
4 Guests
1 Bedroom
1 Bathroom
Apartment
- Oceanfront
- Hot Tub
- Ocean View
US $431/Night
For 7 Nights US $3,017
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $712/Night
For 7 Nights US $4,981
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $332/Night
For 7 Nights US $2,323
1302.43 ft²
6 Guests
2 Bedrooms
2 Bathrooms
House
- Balcony/Terrace
- Pet Friendly
- Parking
US $293/Night
For 7 Nights US $2,051
1200 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $315/Night
For 7 Nights US $2,208
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $226/Night
For 7 Nights US $1,582
5 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $199/Night
For 7 Nights US $1,394
Milwaukee County Large Vacation Homes
1798 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $522/Night
For 7 Nights US $3,652
1614.59 ft²
8 Guests
5 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Parking
- Internet
US $372/Night
For 7 Nights US $2,604
16 Guests
1 Bedroom
1 Bathroom
Pet Friendly
House
- Pet Friendly
- Child Friendly
- Security/Safety
US $706/Night
For 7 Nights US $4,940
1399.31 ft²
12 Guests
5 Bedrooms
2 Bathrooms
Pet Friendly
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $257/Night
For 7 Nights US $1,796
2100 ft²
16 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Kitchen
US $619/Night
For 7 Nights US $4,331
1 ft²
10 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $303/Night
For 7 Nights US $2,124
1141 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $302/Night
For 7 Nights US $2,115
1 ft²
12 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $357/Night
For 7 Nights US $2,497
Why Choose Rent By Owner for your Milwaukee County Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Milwaukee County
When should you plan your Vacation Rentals stay?
Choosing the ideal time to visit here can enhance your experience and help you make the most of your vacation in this destination, whether you're seeking vibrant local events or tranquil exploring opportunities within the region.
Peak Season Highlights
Summer (June to August)
During the summer months, the region experiences lively events and outdoor activities, making it an ideal time for you to enjoy the vibrant atmosphere and take advantage of the warm weather.
Average Temperature Daytime: around 80°F (27°C) - Nighttime: around 65°F (18°C)
Fall (September to November)
As autumn arrives, the area transforms with colorful foliage and cultural festivals, offering a picturesque backdrop for your stay in the region's inviting climate.
Average Temperature Daytime: around 70°F (21°C) - Nighttime: around 50°F (10°C)
Off-Season Highlights
Winter (December to February)
During winter, the region sees fewer visitors, providing a peaceful setting where you can enjoy cozy accommodations and scenic winter landscapes.
Average Temperature Daytime: around 30°F (-1°C) - Nighttime: around 20°F (-6°C)
Spring (March to May)
In early spring, crowds thin out as the weather begins to warm, offering a quieter opportunity to explore and experience the area's natural beauty at your own pace.
Average Temperature Daytime: around 55°F (13°C) - Nighttime: around 40°F (4°C)
Weekly Weather Forecast for Milwaukee County
How to Book Your Milwaukee County 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 County
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 garden area to relax and unwind during your stay.
- Take advantage of a community or private swimming pool for refreshing dips on warm days.
- Make use of well-maintained grilling stations or outdoor kitchens for cookouts with family and friends.
- Benefit from access to nearby parks or green spaces ideal for picnics, walking, or outdoor activities.
- Experience the convenience of designated parking spots or garage space close to your rental.
- Relax in outdoor seating areas designed for socializing or enjoying the scenic views here.
- Explore nearby trails or biking paths perfect for outdoor enthusiasts visiting this destination.
Top Attractions Around Milwaukee County
What attractions are nearby?
In this vibrant region, you can explore a variety of outdoor activities, cultural experiences, and local attractions that showcase the unique charm of Milwaukee County, Wisconsin, all easily accessible from your nearby vacation rentals.
Family Activities
- Milwaukee County Zoo: Spend a day exploring the diverse animal exhibits and interactive programs, perfect for family fun in this region.
- Harley-Davidson Museum: Discover the history of this iconic brand through engaging displays and family-friendly activities located right here.
- Discovery World Science and Technology Center: Engage with hands-on exhibits and aquariums designed to inspire curiosity and learning for children of all ages.
- Milwaukee County Parks: Enjoy outdoor adventures with scenic trails, playgrounds, and picnicking areas throughout the area, ideal for family outings.
Adult Activities
- Milwaukee Art Museum: Discover a world-class collection and stunning architecture that make this museum a must-visit in the area.
- Harley-Davidson Museum: Dive into the history of this iconic brand and enjoy interactive exhibits that appeal to motorcycle enthusiasts.
- Lake Michigan Cruises: Embark on scenic boat tours across Lake Michigan, offering breathtaking views and a relaxing way to explore the region.
- Brewery Tours: Experience Milwaukee's renowned craft beer scene through guided tours at some of the area's best breweries.
Other Places to Stay in Milwaukee County, WI
Milwaukee
Downtown Milwaukee
East Town
Brady Street
Lower East Side
Fifth Ward
Westown
Bay View
Yankee Hill
Wauwatosa
West Allis
Glendale
Milwaukee County Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Visit Around Local Events: Check the area's event calendar to align your stay with festivals or cultural happenings that showcase Milwaukee County's vibrant community.
- Explore Diverse Neighborhoods: Spend time discovering different neighborhoods to experience a wide range of local cuisine, shops, and unique atmospheres during your trip.
- Book Strategically for Convenience: Choose centrally located vacation rentals to easily access the region's top attractions and enjoy more leisure time exploring.
- Utilize Water-Based Activities: Take advantage of nearby lakes and waterways for relaxing boat rides or lakeside strolls that highlight the natural beauty of this destination.
Transportation Options
- Public Transit (Milwaukee County Transit System): You can easily access the region's bus services to navigate around Milwaukee without the need for a car, making it a convenient transportation option for exploring local attractions.
- Amtrak Rail Service: For those looking to travel between cities comfortably, Amtrak offers rail connections that serve the area, providing a scenic and efficient alternative to driving.
- Shared Rides and Taxis: Ride-hailing services and local taxis are readily available here, offering flexible transportation options to reach specific destinations within Milwaukee County.
- Car Rentals: Renting a car allows you to explore more remote areas and attractions at your own pace, giving you the freedom to discover this destination beyond the city limits.
Local Customs Options
- Harbor Festivals: Celebrating Milwaukee’s rich maritime history, harbor festivals in the area are lively events featuring boat parades, live music, and local food vendors that showcase the region's waterfront heritage.
- Beer Traditions: As a city famous for its brewing history, you can experience local customs such as traditional beer tastings and brewery tours that highlight Milwaukee's long-standing beer culture.
- Music and Arts Festivals: The region hosts vibrant music and arts festivals that reflect the diverse cultural influences and creative spirit of this destination’s community.
- Seasonal Celebrations: Seasonal events like winter ice skating and summer outdoor markets embody the local customs, offering you authentic ways to enjoy the area's changing seasons.
Milwaukee County Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Milwaukee County?
There are a lot of options in Milwaukee County. If you plan on staying in the Milwaukee County 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 County:
- Beautiful English Mansion, 1/4 mile from Lake and close to Arts & Entertainment
- Close to airport and downtown Milwaukee!
- Relax Near Everything in Milwaukee
- Amazing view, Modern Space
- Charming, cozy and CENTRAL upper unit in MKE
- Sunny Upper Flat in Shorewood. Great location, great community!
- Groups - Families - Pets - Backyard - Deck
- Gorgeous home just steps from Froedtert/Tosa/MKE
- Cozy Pet Friendly Home w/Private Yard & King Bed - Near Wauwatosa
- Central Milwaukee Haven | Restaurants, Breweries & More
2. How many vacation rentals have private pools in Milwaukee County?
There are 42 vacation rentals with private pools near Milwaukee County. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Milwaukee County are best for families?
If you are looking for a family-friendly vacation home in Milwaukee County, 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 County:
4. How many Rentbyowner vacation rentals are available in Milwaukee County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 2149 in the Milwaukee County 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 County.
5. What is the cancellation policy for vacation rentals in Milwaukee County?
Each listing details its specific cancellation policy, so it’s important to review the terms listed on the property page before booking. If you have questions about flexibility or need to make changes, contacting the property owner directly can provide clarity.
6. How do I ensure my booking is secure and reliable?
Booking through reputable vacation rental platforms ensures your reservation is protected. Always verify the listing's reviews, confirm the property's details, and communicate directly with the owner if needed to ensure a trustworthy stay in this area.
7. Are there any additional fees associated with my stay?
Additional fees such as cleaning, service charges, or taxes are typically specified in the listing details. Make sure to review all fee information before completing your reservation to avoid surprises upon arrival.
8. What amenities are usually included in vacation rentals here?
Most properties offer essential amenities like Wi-Fi, kitchen access, and parking. For specific features such as outdoor spaces or pet-friendliness, check the individual listing details or contact the owner directly.
9. How far in advance should I book a vacation rental in this region?
To secure your preferred property, especially during peak seasons, it’s recommended to book several months in advance. Early planning helps you find the best options tailored to your travel dates.
Milwaukee County Top Rated Vacation Rentals
1878 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Pool
US $382/Night
For 7 Nights US $2,676
581 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $100/Night
For 7 Nights US $697
5 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Kitchen
US $337/Night
For 7 Nights US $2,356
5 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Kitchen
US $161/Night
For 7 Nights US $1,127
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $161/Night
For 7 Nights US $1,126
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $139/Night
For 7 Nights US $974
6458.35 ft²
4 Guests
1 Bedroom
1 Bathroom
Apartment
- Fireplace/Heating
- Pool
- Parking
US $78/Night
For 7 Nights US $546
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Hot Tub
- Fireplace/Heating
- Pool
US $131/Night
For 7 Nights US $916
