South Side Rentals By Owner

There are a lot of options in South Side. If you plan on staying in the South Side 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 Side:

• Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
• 2BR South Loop Apt—Walk to Lake, Museums, Aquarium + Pool, Gym, WiFi, & Conv Ct
• Group-Friendly 6BR Luxury Suite in Prime South Loop Location with Optional Parking and Gym Access Near McCormick Place, Soldier Field and Grant Park
• McCormick 3BR HUGE unit, Optional Parking with Ping-pong
• McCormick Place 2BR Suite with Patio, Skyline View and Optional Parking Sleeps 6 Near Soldier Field and Grant Park
• South Loop 3BD 2BA Condo with Balcony and Parking
• Modern 2BR Stay in South Loop with Optional Parking & Gym Access Near Museum Campus & Grant Park
• Spacious 2BR South Loop Suite with Skyline View, Optional Parking and Gym Access Close to McCormick Place, Grant Park, Museum Campus & CTA Lines
• Charming 2BR Apartment with Skyline view, Optional Parking & Gym Access Near McCormick Place, Lakefront and Soldier Field
• Cozy 3BR City Living in South Loop Near McCormick Place, Soldier Field & Lakefront

There are many large, family-friendly vacation homes available in South Side; however, here are the most popular family rentals listed on our site:

• Luxéry Stay "Hollywood" Downtown/McCormick/WinTrust Area
• Cozy 2BR South Loop Condo with Optional Parking and Gym Near McCormick Place, Public Transit & City Hotspots
• Spacious 5BR Chicago Suite Near McCormick Place & Soldier Field
• Stylish 2BR South Loop Family Unit Near McCormick Place & Soldier Field

Yes, there are 458 self-catering vacation homes in South Side that have hot tubs, swimming pools, & other amenities.

There are more than 458 luxury villas and vacation homes in or near South Side. Filter by price to compare find the most expensive places to stay on Inclusiveholidays.

Yes, there are 458 pet friendly vacation homes and places to stays that are available in or near South Side that you may consider.