Apartment holiday rentals in South Side
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Top-rated apartment rentals in South Side
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for South Side apartment rentals
Weekly apartment rentals
Rental unit in Chicago
2 bedroom apartment near train line and bus lines!
Rental unit in Chicago
Chicago Vintage Home
Rental unit in Chicago
Urban Pilsen Apt. near Downtown
Rental unit in Chicago
Bright, Gorgeous Apt Private Parking available
Rental unit in Chicago
Handicap accessible apartment w/Level-2 EV Charger
Rental unit in Chicago
Spacious 2BR on Quiet St - Free Park/Late Checkout
Rental unit in Chicago
A Vintage Pink House in the Heart of Chicago
Rental unit in Chicago
Humboldt Park Loft
Private apartment rentals
Rental unit in Chicago
Ground-Level Speakeasy: 1BR-1.5BA Near Everything!
Rental unit in Chicago
Your Perfect Spot :)-With Memory Foam Mattress!
Rental unit in Chicago
Urban Cottage
Rental unit in Chicago
Stunning Basement Apartment w/free street parking!
Rental unit in Chicago
Lovely 1-BR Apt with full kitchen & living room
Rental unit in Chicago
Beverly Cottage Loft
Rental unit in Chicago
Vela Loft w/2 BR & Modern Design
Rental unit in Chicago
Comfortable and Cozy Apartment
Apartment rentals with a hot tub
Rental unit in Berwyn
“Dream slice of urban homesteading.”
Rental unit in Chicago
Checkerboard Studio with Private Outdoor Hot Tub and Yard
Rental unit in Chicago
Skyline Serenity: Sauna, Hot Tub, Peloton, Views
Rental unit in Chicago
Cloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Rental unit in Chicago
Luxe Suite + Spa House Retreat! Pets Welcome
Rental unit in Chicago
The Areal Oasis
Rental unit in Chicago
Spectacular Rooftop Getaway in Heart of City
Rental unit in Chicago
Lake, City, & River View Condo
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Schaumburg Holiday rentals
- Chicago Holiday rentals
- Serviced apartment rentals United States
- Flat rentals United States
- Flat rentals Chicago
- Flat rentals Chicago
- Flat rentals Downtown Chicago
- Rentals with outdoor seating South Side
- Rentals with a washing machine and dryer South Side
- Apartment rentals South Side
- Rentals with a fireplace South Side
- Waterfront rentals South Side
- Rentals with breakfast South Side
- Monthly Rentals South Side
- Townhouse rentals South Side
- Family-friendly rentals South Side
- Rentals with beach access South Side
- Rentals with a firepit South Side
- Family-friendly rentals South Side
- Rentals with a hot tub South Side
- Pet-friendly rentals South Side
- Rentals with an EV charger South Side
- Rentals with pools South Side
- House rentals South Side
- Smoking-friendly rentals South Side
- Rentals with lake access South Side
- Fitness-friendly rentals South Side
- Rentals with a patio South Side
- Private suite rentals South Side
- Flat rentals Milwaukee
- Flat rentals Illinois
- Flat rentals Cook County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom