What are the top rated Vacation Rentals in South Side?

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: <a href="/property/chic-2-bedroom-townhouse-with-rooftop-free-parking-in-downtown-chicago/HA-3212709701" class="class="static-page-link"">Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!</a> <a href="/property/2br-south-loop-apt-walk-to-lake-museums-aquarium-pool-gym-wifi-conv-ct/HA-3214526812" class="class="static-page-link"">2BR South Loop Apt—Walk to Lake, Museums, Aquarium + Pool, Gym, WiFi, &amp; Conv Ct</a> <a href="/property/south-loop-3bd-2ba-condo-with-balcony-and-parking/HA-3214404170" class="class="static-page-link"">South Loop 3BD 2BA Condo with Balcony and Parking</a> <a href="/property/cozy-3br-city-living-in-south-loop-near-mccormick-place-soldier-field-lakefront/BC-11391307" class="class="static-page-link"">Cozy 3BR City Living in South Loop Near McCormick Place, Soldier Field &amp; Lakefront</a> <a href="/property/group-friendly-spacious-3br-suite-with-optional-parking-and-gym-access-sleeps-10-guest-near-mccormic/BC-9546852" class="class="static-page-link"">Group Friendly Spacious 3BR Suite with Optional Parking and Gym Access Sleeps 10 Guest Near McCormick Place and Soldier Field</a> <a href="/property/mccormick-place-2br-suite-with-patio-skyline-view-and-optional-parking-sleeps-6-near-soldier-field-a/BC-9710642" class="class="static-page-link"">McCormick Place 2BR Suite with Patio, Skyline View and Optional Parking Sleeps 6 Near Soldier Field and Grant Park</a> <a href="/property/modern-420-friendly-3br-unit-near-mccormick-lakefront/HA-3213424221" class="class="static-page-link"">Modern 420-Friendly 3BR Unit Near McCormick &amp; Lakefront</a> <a href="/property/stylish-3br-gem-in-prime-location/BC-15189070" class="class="static-page-link"">Stylish 3BR Gem in Prime Location</a> <a href="/property/mccormick-place-patio-skyline-2b-2b-with-optional-parking-for-up-to-6-people/HA-3213424217" class="class="static-page-link"">McCormick Place Patio skyline 2b/2b with optional Parking for up to 6 people</a> <a href="/property/spacious-3br-suite-south-loop-chicago-near-mccormick-place-soldier-field/HA-3213532544" class="class="static-page-link"">Spacious 3BR Suite South Loop Chicago Near McCormick Place &amp; Soldier Field</a>

Which is the best family rental in South Side?

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 Spacious 6BR Luxury Suite Perfect for Groups Near McCormick Place and Soldier Field Spacious 5BR Chicago Suite Near McCormick Place & Soldier Field Stylish 2BR South Loop Family Unit Near McCormick Place & Soldier Field

Can we get self-catering vacation rentals in South Side?

Yes, there are 451 self-catering vacation homes in South Side that have hot tubs, swimming pools, & other amenities.

What are the best luxury vacation rentals near South Side?

There are more than 451 luxury villas and vacation homes in or near South Side. Filter by price to compare find the most expensive places to stay on Smartours.