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Discover Your Perfect South Shore Rentals by Owner

South Shore Rentals by Owner

10.0 (1 Review)
House
Merrill
  • Air Conditioner
  • Parking
  • Balcony/Terrace
View Availability
More Top-Rated Rentals by Owner in South Shore Area

Why Choose Rent By Owner for your South Shore vacation rental?

What makes our Rentals by Owner 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 South Shore Rentals by Owner

Where are the best neighborhoods to stay in South Shore?

When exploring South Shore in Chicago, Illinois, choosing the right neighborhood to stay in can greatly enhance your visit. This area offers a variety of rental options by owner, providing you with a comfortable and authentic experience. Whether you prefer to be close to local community amenities or seeking a quiet retreat, South Shore's neighborhoods have something to offer every traveler. By booking through Rent By Owner, you can enjoy a seamless and dependable process, ensuring your accommodation aligns perfectly with your plans and expectations in this vibrant part of Chicago.

Jackson Park Highlands

Within this peaceful neighborhood, you can enjoy a quiet yet accessible location that offers a unique blend of historic charm and modern convenience. It’s an ideal choice for those seeking a comfortable stay close to Chicago's vibrant attractions.

View 460+ Rentals in Jackson Park Highlands

Best Times to Visit South Shore

When should you plan your Rentals by Owner stay?

Choosing the ideal time to vacation in this destination can enhance your experience, as understanding seasonal trends and local climate patterns allows you to plan ahead for a memorable stay here.

Peak Season Highlights

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Summer (June to August)

During the peak summer months, you can enjoy warm weather ideal for outdoor activities and exploring the vibrant local scene.

Average Temperature Daytime: around 80-85°F - Nighttime: 65-70°F
autumn
Fall (September to November)

Autumn offers a pleasant climate with colorful foliage, making it a great time to experience the area's natural beauty and cultural events.

Average Temperature Daytime: 70-75°F - Nighttime: 50-55°F

Off-Season Highlights

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Winter (December to February)

The winter months bring cooler temperatures, providing a quieter atmosphere perfect for cozy stays and off-season rates.

Average Temperature Daytime: 30-40°F - Nighttime: 20-30°F
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Spring (March to May)

As the region awakens from winter, spring features milder weather and fewer crowds, ideal for enjoying outdoor recreational activities.

Average Temperature Daytime: 55-65°F - Nighttime: 40-50°F

Weekly Weather Forecast for South Shore

How to Book Your South Shore vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 South Shore

More Top-Rated Rentals by Owner in South Shore Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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 outdoor seating areas such as patios or decks to relax and socialize.
  • Take advantage of well-maintained gardens or landscaped yards for a touch of nature during your stay.
  • Make the most of shared or private grilling stations to host outdoor cookouts.
  • Utilize dedicated outdoor dining spaces perfect for enjoying meals al fresco.
  • Benefit from access to outdoor pools or hot tubs, ideal for unwinding after a day of exploring.
  • Explore nearby walking paths or trails that allow you to experience the area's natural beauty.
  • Visit outdoor recreational facilities like playgrounds or sports courts available at some rentals in this region.

Top Attractions Around South Shore

What attractions are nearby?

Within this vibrant neighborhood, you can enjoy a variety of nearby activities, from exploring scenic lakeside parks to engaging in local cultural events, offering a memorable stay in the area through your Rent By Owner rental.

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Family Activities

  • Chicago Children's Museum at Navy Pier: Explore interactive exhibits and engaging activities designed specifically for families to enjoy in this vibrant area.
  • South Shore Cultural Center: Participate in family-friendly events, outdoor activities, and cultural programs held at this historic community hub.
  • Calumet Park: Spend quality time outdoors with picnicking, playgrounds, and scenic views perfect for a relaxing family day in the region.
  • Lake Michigan Beaches: Unwind on the sandy shores, build sandcastles, or take a refreshing dip at the nearby beaches popular with local families.
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Adult Activities

  • South Shore Cultural Center Tour: Explore the historic architecture and vibrant art exhibitions hosted at this cultural hub, offering an enriching experience close to your rental.
  • Lakeside Walking and Biking: Enjoy scenic routes along Lake Michigan's shoreline for a rejuvenating walk or bike ride with picturesque views just moments from here.
  • South Shore Golf Course: Play a round of golf at this well-maintained course that provides a relaxing escape and a chance to sharpen your skills within the neighborhood.
  • Fishing and Boating on Lake Michigan: Engage in fishing or rent a boat to explore the waters, making the most of the area's prime lakeside location for outdoor leisure.

Other Places to Stay in South Shore, IL

South Shore Golf Course
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Jackson Park Hospital
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Arthur Ashe Beach
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Rainbow Beach
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South Shore Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Neighborhoods: Take time to walk through the nearby residential areas to experience the authentic charm of this part of Chicago and discover hidden local gems.
  • Plan Your Transportation: Familiarize yourself with public transit options and parking facilities in the region to navigate easily during your stay.
  • Visit Nearby Parks and Beaches: Utilize the outdoor spaces close to your rental for relaxing days and scenic views that highlight the area's natural beauty.
  • Discover Local Dining Options: Savor the regional flavors at local eateries, giving you a taste of this destination's culinary scene while staying conveniently close to your accommodation.

Transportation Options

  • Chicago Transit Authority (CTA) Bus and Train Services: You can conveniently access a comprehensive network of bus and train routes that connect the area to downtown Chicago and beyond, making travel straightforward.
  • Metra Commuter Rail: The local Metra station offers an efficient railway option for travelers looking to reach various suburbs and central Chicago with ease from this part of the region.
  • Ride-Sharing Services: Popular ride-sharing companies operate extensively here, providing on-demand transportation that is flexible and reliable for exploring the region at your own pace.
  • Rental Car Services: Numerous rental agencies are available nearby, giving you the freedom to navigate the broader region independently and at your convenience from this destination.

Local Customs Options

  • Respect for Local Traditions: It’s customary to honor the community’s traditional events and celebrations when visiting here, enhancing your cultural experience in the area.
  • Politeness and Greetings: Greeting neighbors with a friendly nod or wave is appreciated and reflects the warm hospitality of this destination.
  • Community Engagement: Participating in neighborhood gatherings or local festivals can enrich your stay and help you connect with residents of the region.
  • Respect for Public Spaces: Maintaining cleanliness and following guidelines in parks and public areas demonstrates your respect for the community’s environment and shared spaces.

Frequently Asked Questions About South Shore Rentals by Owner

1. What are the top vacation rentals in South Shore?

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

2. How many Rentbyowner vacation rentals are available in South Shore?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 31 in the South Shore 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 South Shore. 

3. What is the cancellation policy for rental by owner accommodations in South Shore, Chicago?

The cancellation policy varies depending on the individual host's terms listed in the rental listing. It is recommended to review the specific policy before booking and contact the host directly if you have any questions about cancellations.

4. How do I communicate with the property owner before booking a rental in South Shore?

You can contact the property owner through the messaging system provided on the Rent By Owner platform. It's advisable to ask all relevant questions and confirm details prior to completing your reservation.

5. Are there any specific check-in and check-out procedures for rentals by owner in this neighborhood?

Check-in and check-out procedures are typically outlined in the listing details. It's best to review these instructions and reach out to the owner if you need further clarification to ensure a smooth stay.

6. Can I find pet-friendly rental options in South Shore through Rent By Owner?

Yes, many hosts offer pet-friendly accommodations. Be sure to filter your search accordingly and read the pet policy details on each listing to understand any restrictions or additional fees.

7. What amenities are usually included in rentals by owner here in South Shore, Chicago?

Amenities vary by listing, but common features include Wi-Fi, kitchen facilities, parking, and laundry services. To confirm what’s available, review the listing descriptions carefully and contact the owner if necessary.

More Rentals You May Like Near South Shore

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Luxury off the Lake
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  • Bedding/Linens
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