Best Vacation Homes in Milwaukee County
House
6.0(1 Review)
10 Bedrooms
5 Baths
30 Guests
4596 ft²
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
US $1,166/Night
7 Nights - US $8,160
Apartment
10.0(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
1130.21 ft²
Air Conditioner
Internet
Child Friendly
Wheelchair Accessible
US $276/Night
7 Nights - US $1,932
Bed & Breakfast
9.8(117 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Breakfast- Kitchen
US $218/Night
7 Nights - US $1,527
New
Condo
2 Bedrooms
1 Bath
5 Guests
1200 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
Parking
US $556/Night
7 Nights - US $3,890
House
10.0(5 Reviews)
3 Bedrooms
3 Baths
8 Guests
1506.95 ft²
Hot Tub- Balcony/Terrace
- Kitchen
- Parking
US $264/Night
7 Nights - US $1,851
New
Apartment
2 Bedrooms
1 Bath
6 Guests
1033 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $473/Night
7 Nights - US $3,311
New
Apartment
2 Bedrooms
1 Bath
6 Guests
1033 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $436/Night
7 Nights - US $3,051
House
4 Bedrooms
2 Baths
12 Guests
1600 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $412/Night
7 Nights - US $2,886
Milwaukee County Luxury Rentals
Hotel
6.8(36 Reviews)
1 Bath
386.43 ft²
Private Pool
Oceanfront- Hot Tub
Spa
US $3,000/Night
7 Nights - US $21,000
House
1 Bedroom
3 Baths
20 Guests
View- Parking
- Air Conditioner
- Internet
US $2,651/Night
7 Nights - US $18,557
House
6 Bedrooms
3 Baths
16 Guests
10763.91 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Air Conditioner
US $2,166/Night
7 Nights - US $15,162
House
9.0(2 Reviews)
9 Bedrooms
4 Baths
29 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $1,919/Night
7 Nights - US $13,433
House
10.0(20 Reviews)
5 Bedrooms
4 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $1,906/Night
7 Nights - US $13,341
House
9.8(17 Reviews)
4 Bedrooms
3 Baths
16 Guests
2497.23 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
US $1,677/Night
7 Nights - US $11,739
House
9.8(27 Reviews)
6 Bedrooms
5 Baths
30 Guests
4766 ft²
- Oceanfront
- Fireplace/Heating
Ocean View- Balcony/Terrace
US $1,656/Night
7 Nights - US $11,595
Hotel
4 Baths
- Fireplace/Heating
Pool- Breakfast
- Kitchen
US $1,610/Night
7 Nights - US $11,270
Milwaukee County Pet Friendly Vacation Rentals
New
House
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $115/Night
7 Nights - US $804
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
4 Guests
538.2 ft²
- Oceanfront
- Hot Tub
- Ocean View
- View
US $431/Night
7 Nights - US $3,017
Cottage
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $712/Night
7 Nights - US $4,981
Villa
10.0(31 Reviews)
2 Bedrooms
2 Baths
6 Guests
1141 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $564/Night
7 Nights - US $3,951
House
10.0(1 Review)
2 Bedrooms
1 Bath
8 Guests
1205.56 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Parking
US $300/Night
7 Nights - US $2,102
House
10.0(20 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $351/Night
7 Nights - US $2,455
House
10.0(16 Reviews)
2 Bedrooms
1 Bath
6 Guests
1200 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $498/Night
7 Nights - US $3,489
House
10.0(10 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $226/Night
7 Nights - US $1,582
Milwaukee County Large Vacation Homes
Villa
10.0(45 Reviews)
2 Bedrooms
2 Baths
8 Guests
1798 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $616/Night
7 Nights - US $4,312
House
10.0(1 Review)
5 Bedrooms
2 Baths
12 Guests
1399.31 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $257/Night
7 Nights - US $1,796
House
4 Bedrooms
3 Baths
12 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Parking
US $540/Night
7 Nights - US $3,780
House
10.0(4 Reviews)
4 Bedrooms
2 Baths
16 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $495/Night
7 Nights - US $3,466
Apartment
10.0(1 Review)
13 Bedrooms
4 Baths
8 Guests
767.83 ft²
- Air Conditioner
- Internet
- Child Friendly
Wellness Facilities
US $249/Night
7 Nights - US $1,743
Condo
10.0(3 Reviews)
2 Bedrooms
2 Baths
16 Guests
2100 ft²
- Hot Tub
- Fireplace/Heating
- Kitchen
- Parking
US $627/Night
7 Nights - US $4,387
Villa
10.0(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
1098 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $454/Night
7 Nights - US $3,180
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
10 Guests
1 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $379/Night
7 Nights - US $2,656
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
Westown
Fifth Ward
Yankee Hill
Bay View
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.
Frequently Asked Questions About Milwaukee County?
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
- Charming, cozy and CENTRAL upper unit in MKE
- Amazing view, Modern Space
- Sunny Upper Flat in Shorewood. Great location, great community!
- Groups - Families - Pets - Backyard - Deck
- Cozy Pet Friendly Home w/Private Yard & King Bed - Near Wauwatosa
- Large Victorian in Perfect Location!
- Modern Comfort in Historic Milwaukee | Sleeps 8
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 2174 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
House
10.0(25 Reviews)
3 Bedrooms
3 Baths
8 Guests
1878 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $382/Night
7 Nights - US $2,674
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
5 Guests
775 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $384/Night
7 Nights - US $2,690
Hotel
10.0(2 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
US $373/Night
7 Nights - US $2,612
Hotel
10.0(1 Review)
3 Baths
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
US $1,173/Night
7 Nights - US $8,214
Hotel
10.0(1 Review)
1 Bath
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
US $426/Night
7 Nights - US $2,984
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
5 Guests
775 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $309/Night
7 Nights - US $2,166
Condo
10.0(1 Review)
1 Bedroom
1 Bath
4 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Breakfast
US $176/Night
7 Nights - US $1,233
Condo
10.0(1 Review)
1 Bedroom
1 Bath
4 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Breakfast
US $161/Night
7 Nights - US $1,126
