Best Vacation Homes in Southern Wisconsin
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Southern Wisconsin Luxury Rentals
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Southern Wisconsin Pet Friendly Vacation Rentals
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Southern Wisconsin Large Vacation Homes
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Why Choose Rent By Owner for your Southern Wisconsin Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for Southern Wisconsin Vacation Rentals
Where are the best neighborhoods to stay in Southern Wisconsin?
When planning your stay in Southern Wisconsin, exploring its diverse neighborhoods can significantly enhance your experience. Each area offers a unique blend of local charm and scenic beauty, making it easy to find the perfect setting for your getaway. Whether you're seeking a quiet retreat or a lively community, you'll discover neighborhood options that suit your preferences for relaxation and adventure. Booking your vacation rentals in this region ensures access to authentic local experiences and convenient amenities, creating a memorable trip tailored to your interests. Trustworthy and dependable accommodations are available throughout Southern Wisconsin, making your search for an ideal place to stay both simple and satisfying.
Historic Third Ward
Situated in the heart of Milwaukee, this neighborhood offers a vibrant atmosphere with charming architecture and cultural attractions, making it an ideal location for exploring the city's artistic side. Staying here puts you close to trendy shops, galleries, and lakeside parks, providing a perfect blend of urban excitement and relaxation.
View 911+ Rentals in Historic Third WardHistoric Downtown La Crosse
This historic district provides a picturesque setting within La Crosse, featuring beautiful architecture and scenic river views that enhance your stay. It's an excellent choice for discovering local heritage and enjoying riverfront activities right at your doorstep.
View 183+ Rentals in Historic Downtown La CrosseEast Town
Located on Milwaukee’s east side, this lively neighborhood offers convenient access to cultural venues, dining options, and outdoor spaces. Here, you can experience the energetic vibe of the city while remaining close to key attractions.
View 465+ Rentals in East TownNorth Milwaukee
North Milwaukee presents a diverse community with easy access to both natural parks and urban amenities. It’s an ideal base for travelers seeking a mix of outdoor recreation and city exploration.
View 110+ Rentals in North MilwaukeeSpring Brook
Nestled near Wisconsin Dells’ famous attractions, Spring Brook provides peaceful surroundings perfect for relaxing after days of adventure. Its tranquil environment makes it suitable for families or those looking for a restful retreat.
View 98+ Rentals in Spring BrookMarquette
Known for its vibrant community, Marquette offers a central location with access to Milwaukee's dynamic nightlife, eateries, and cultural sites. Staying here gives you a convenient gateway to the region’s best urban experiences.
View 880+ Rentals in MarquetteDowntown
In the heart of Sheboygan, this downtown area boasts a lively scene with restaurants, shops, and entertainment options, perfect for immersing yourself in the local culture. It provides easy access to the waterfront and city amenities.
View 235+ Rentals in DowntownMaplewood
Situated in a family-friendly neighborhood, Maplewood offers a quiet yet accessible setting within Milwaukee, ideal for travelers seeking comfort and convenience. Close to parks and local attractions, it’s a great spot for a relaxed stay.
View 42+ Rentals in MaplewoodBest Times to Visit Southern Wisconsin
When should you plan your Vacation Rentals stay?
Choosing the right time to visit ensures your stay here in Southern Wisconsin is both enjoyable and memorable, allowing you to experience the region’s natural beauty and local charm at its best.
Peak Season Highlights
Summer (June to August)
This is the most popular time to visit the area, with warm weather and extended daylight hours perfect for outdoor activities. Booking your vacation rentals early ensures you secure the best options during this busy season.
Fall (September to November)
Experience the region’s vibrant autumn colors, attracting visitors seeking scenic views and outdoor adventures. Securing a vacation rental ahead of time guarantees a comfortable stay amid the stunning fall scenery.
Off-Season Highlights
Winter (December to February)
During these colder months, fewer travelers make it easier to find cozy vacation rentals at competitive rates. It’s a quiet time to enjoy peaceful surroundings and seasonal tranquility.
Spring (March to May)
As the region transitions into warmer weather, spring offers mild temperatures and blooming landscapes. Off-peak visits provide an opportunity for relaxed booking and exploring without the crowds.
Weekly Weather Forecast for Southern Wisconsin
How to Book Your Southern Wisconsin Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Southern Wisconsin
Common Vacation Rentals Amenities
What amenities can you expect?
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 outdoor seating areas such as patios or decks to relax and take in the surrounding scenery.
- Benefit from access to private or communal fire pits perfect for evening gatherings and roasting marshmallows.
- Take advantage of spacious yards or gardens ideal for outdoor activities and leisure.
- Make use of on-site grills or BBQ facilities to prepare meals amidst the fresh air.
- Access nearby hiking trails or nature paths that showcase the natural beauty of this destination.
- Utilize outdoor recreational equipment such as kayaks, paddleboards, or bicycles available for guest use.
- Relish in scenic views from outdoor vantage points that highlight the region’s picturesque landscape.
Top Attractions Around Southern Wisconsin
What attractions are nearby?
In this region, you can enjoy a variety of outdoor activities such as exploring scenic parks, engaging in watersports on nearby lakes, or discovering charming local towns, making it an ideal destination for those seeking adventure and relaxation close to your Southern Wisconsin vacation rentals.
Family Activities
- Wisconsin Dells Water Park Adventure: Spend a thrilling day exploring the area's renowned water parks, where you can enjoy slides, wave pools, and lazy rivers perfect for family fun.
- Devil's Lake State Park Hiking and Nature Activities: Discover scenic hiking trails, stunning views, and outdoor exploration in this natural sanctuary ideal for active families staying nearby.
- Circus World Museum Experience: Introduce your family to the magic of the circus through engaging exhibits and live performances at this popular regional attraction.
- Madison Children's Museum: Ignite your children’s curiosity with interactive exhibits and educational activities designed to entertain and inspire in the state's vibrant capital city.
Adult Activities
- Wine Tasting Tours: Explore the region's renowned wineries and indulge in tasting sessions that showcase local wines crafted with regional expertise.
- Visit Historic Sites: Dive into the area's rich history by exploring historic landmarks and museums that highlight its cultural heritage.
- Golfing Experiences: Enjoy a round of golf at some of the region’s top courses, perfect for relaxing and taking in picturesque views.
Other Places to Stay in Southern Wisconsin, WI
Southern Wisconsin Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Cuisine: Take the opportunity to indulge in regional dishes at local eateries, which beautifully showcase the area's culinary traditions.
- Visit Natural Attractions: Make the most of your stay by exploring nearby parks and nature reserves that highlight the scenic beauty of this destination.
- Plan Seasonal Activities: Tailor your plans around seasonal events and outdoor activities to experience the region's vibrant local culture throughout the year.
- Choose a Well-Located Vacation Rental: Select accommodations with easy access to key attractions, ensuring a comfortable and convenient base during your visit here.
Transportation Options
- Intercity Bus Services: These services connect you to major cities and towns in the area, offering an affordable and convenient way to explore here without a car.
- Regional Rail Lines: Traveling by train provides scenic routes through the region, making it a comfortable option for reaching nearby destinations within Southern Wisconsin.
- Local Transit Systems: Public bus networks serve key neighborhoods and attractions, helping you navigate with ease during your stay in this area.
- Private Car Rentals: Renting a vehicle gives you flexibility and freedom to discover all the hidden gems of the region at your own pace.
Local Customs Options
- Fiddle Music Traditions: You can experience the region's lively fiddle music, which plays a vital role in local festivals and gatherings, reflecting the area's rich cultural heritage.
- Farmers’ Markets and Food Customs: Visiting farmers' markets is common here, where fresh, locally sourced produce and traditional Wisconsin foods showcase the area's agricultural roots.
- Community Festivals and Parades: Participating in seasonal festivals and parades is a cherished custom, celebrating regional history and fostering community spirit.
- Respect for Nature and Outdoor Activities: Embracing outdoor pursuits like boating, fishing, and hiking aligns with local customs that honor the natural beauty of this destination.
Frequently Asked Questions About Southern Wisconsin?
1. What are the top vacation rentals in Southern Wisconsin?
There are a lot of options in Southern Wisconsin. If you plan on staying in the Southern Wisconsin area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Southern Wisconsin:
- Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
- Secluded, Romantic, Family Friendly and Cozy, Last House in the Valley.
- Nature Lover's Paradise In The Driftless Area Of Southern Wisconsin, USA.
- The Honey Barn & Honey House LLC
- A Home Away from Home in the Quaint Village of New Glarus
- Rocky Glen Condo - forest nest on Baraboo bluff
- Private Beach & Pier Lake Front w/Fireplace on Lake Como - Walk to Mars Resort!
- Legendary Moose Lodge
- Seagull Beach Guest House, Unique Lake Michigan Cottagenon private beach
- Arcadian Cabin at Bishop Branch, creek-front, public land access, great location
2. How many vacation rentals have private pools in Southern Wisconsin?
There are 581 vacation rentals with private pools near Southern Wisconsin. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Southern Wisconsin are best for families?
If you are looking for a family-friendly vacation home in Southern Wisconsin, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Southern Wisconsin:
4. How many Rentbyowner vacation rentals are available in Southern Wisconsin?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 11942 in the Southern Wisconsin 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 Southern Wisconsin.
5. What is the cancellation policy for vacation rentals in Southern Wisconsin?
6. How do I confirm my reservation at a vacation rental in this region?
7. Are there any additional fees or deposits required when booking a vacation rental here?
8. What amenities are typically included in vacation rentals in Southern Wisconsin?
9. How can I communicate special requests or questions about my stay in this destination?
Southern Wisconsin Top Rated Vacation Rentals
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