South Side Villa Rentals

Frequently Asked Questions About South Side?

What are the top hotels or resorts in South Side?

We provide an array of great vacation destinations in South Side. If you are looking to stay in or around the South Side area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in South Side:

• MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
• 1 #33 - 4 Bedroom/2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
• Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
• Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
• Luxéry Stay "Hollywood" Downtown/McCormick/WinTrust Area
• Stylish 2BR South Loop Family Unit Near McCormick Place & Soldier Field
• Luxéry Stay "Chicago" Downtown/McCormick/Wintrust Area
• 2BR South Loop Apt—Walk to Lake, Museums, Aquarium + Pool, Gym, WiFi, & Conv Ct
• Comfy 3BR Chicago Retreat 420 Friendly Unit Near McCormick Place & Soldier Field
• Spacious 6BR Luxury Suite Perfect for Groups Near McCormick Place and Soldier Field

How many vacation rentals have private pools in South Side?

We have 4 luxury villas and vacation rentals featuriung a private pool in and near South Side. Some of the best destinations to stay that feature or have access to a swimming pool are:

• S Loop 2BR w Pool Gym Spa nr Grant Park CHI-740
• Blueground South Loop pool golf sim nr museum CHI-1047
• Hilton Garden Inn Chicago Downtown South Loop
• Hilton Garden Inn Chicago McCormick Place

Which hotel or resort in South Side is best for families?

Searching for a family-friendly getaway in South Side? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

• McCormick Place 2b/2b family unit with optional parking for up to 8 guests
• Charming 2BR Apartment with Skyline view, Optional Parking & Gym Access Near McCormick Place, Lakefront and Soldier Field
• Marriott Marquis Chicago

How many hotels, resorts, or rentals are available in South Side?

BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2026 is over 526 in the South Side area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in South Side. 

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