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Vacation rentals in South Side

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Top-rated vacation rentals in South Side

Guests agree: these stays are highly rated for location, cleanliness, and more.

Private Studio in Bridgeport, Chicago
SUPERHOST
Entire guesthouse · 3 guests · 1 bed · 1 bath
Private Studio in Bridgeport, ChicagoA bright studio guesthouse, perfect for business travelers, a couple’s getaway, personal retreat, or a solo adventurer. Has a kitchen sink, cabinet space for your non-perishable items, a microwave, mini-fridge, and Keurig. We provide plates, flatware, mugs, and glasses. The studio offers the privacy of your own bathroom and shower facilities. You'll rest well in a full-size Murphy bed, with sufficient storage for all your travel items. A couch is available for a third guest if needed.
Polk Street Coach House Apartment, Little Italy/Medical Dist
PLUS
Entire guesthouse · 6 guests · 2 beds · 1 bath
Polk Street Coach House Apartment, Little Italy/Medical DistCook in a kitchen with everything from a KitchenAir convection range and Kitchen Aid food processor to Calphalon pots and pans. The mid-century look includes a comfy American Leather sofa, Gansgo Mobler dining table, and Frem Rolje teak chairs.
La Casita II
SUPERHOST
Entire rental unit · 4 guests · 2 beds · 1 bath
La Casita IINice Cozy and welcoming place. Easy access to public transportation. 10 to 15 minutes from downtown, museums, Sox and Bullsstadiums. Located in the colorful and lively neighborhood of Pilsen and close to Little Italy. Smart devices installed for easy check-in and safety (extremely accurate and sensitive smoke detector warning all occupants of possible problems). Guest wifi included with some feel home amenities.

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Popular amenities for South Side vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in South Side

PLUS
  1. Entire rental unit
  2. Chicago
Bright, Modern Apartment in a Vintage Greystone
$139 per night
SUPERHOST
  1. Private room
  2. Chicago
In the heart of Pilsen, Self Check In
$47 per night
SUPERHOST
  1. Private room
  2. Chicago
Restoring Chicago Speakeasy from 1920's Room 1A
$100 per night
SUPERHOST
  1. Private room
  2. Chicago
SHARED Artist Loft . Very Unique
$99 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Royal Coach House Cottage
$108 per night
  1. Private room
  2. Chicago
Amazing&Comfy 1 Bed 1 Bath Condo in great location
$60 per night
SUPERHOST
  1. Entire serviced apartment
  2. Chicago
PRIVATE 2-bedroom 1.5 bath w/ living room
$79 per night
  1. Private room
  2. Chicago
Charming Basement with Private Bath- Sleeps 2
$20 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!
$164 per night
PLUS
  1. Entire residential home
  2. Chicago
Get Cozy at a Powder-Blue Residence in the Heart of Pilsen
$101 per night
SUPERHOST
  1. Private room
  2. Chicago
HydePark007, Chinatown, UC, NavyPier, freeparking
$60 per night
SUPERHOST
  1. Entire condominium (condo)
  2. Chicago
Modern Hyde Park Getaway | UChicago
$91 per night