Apartment holiday rentals in South Side
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Top-rated apartment rentals in South Side
Guests agree: these apartments are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for South Side apartment rentals
Weekly apartment rentals
Apartment in Chicago
4.87 out of 5 average rating, 110 reviewsSpacious Duplex in Great Location
Apartment in Chinatown
4.83 out of 5 average rating, 161 reviewsSecluded 2BR APT in Chinatown by McCormick/DWTN
Apartment in Chicago
4.81 out of 5 average rating, 447 reviewsCozy Apartment with Free On-Site Parking
Apartment in Chicago
4.91 out of 5 average rating, 234 reviewsModern/Spacious 2BR/2BA West Town
Apartment in Chicago
4.98 out of 5 average rating, 209 reviewsNear Lake Michigan & Wrigley Field
Apartment in Chicago
5.0 out of 5 average rating, 107 reviewsSpacious 4 Bedroom Condo
Apartment in Oak Park
4.96 out of 5 average rating, 131 reviewsPicture Perfect 3Bed Steps from Train and FLW
Apartment in Chicago
4.94 out of 5 average rating, 178 reviewsCharming Chinatown Home by McCormick★Downtown
Pet-friendly apartment rentals
Apartment in Evanston
4.77 out of 5 average rating, 571 reviewsSpacious Evanston Unit - Walk to Northwestern U
Apartment in Chicago
4.99 out of 5 average rating, 220 reviews❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D
Apartment in Chicago
4.93 out of 5 average rating, 191 reviewsPvt 1bdr Rogers Park, Loyola, Northwestern.
Apartment in Chicago
4.78 out of 5 average rating, 202 reviewsModern Luxury In Old Town - Sleeps 4
Apartment in Chicago
4.83 out of 5 average rating, 312 reviewsChic and Charming Vintage Condominium in Lincoln Park
Apartment in The Loop
4.8 out of 5 average rating, 171 reviewsMICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
Apartment in Chicago
4.82 out of 5 average rating, 119 reviewsCharming Condo near U.C./Loop/McCormick Place
Apartment in Chicago
4.91 out of 5 average rating, 304 reviewsSusie's Space. 2BR easy parking & pet friendly
Apartment rentals with a pool
Apartment in Chicago
4.75 out of 5 average rating, 150 reviewsCentral Downtown Location-Modern 2BR Condo
Apartment in Evanston
4.91 out of 5 average rating, 104 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Apartment in Portage
4.93 out of 5 average rating, 81 reviewsCozy 1 bedroom condo on Marina near Lake Michigan
Apartment in Lisle
4.96 out of 5 average rating, 47 reviewsPeaceful Condo in Lisle, Illinois
Apartment in Portage
5.0 out of 5 average rating, 55 reviewsLuxury Waterfront 2 Bedroom Condo by Lake Michigan
Apartment in Portage
4.93 out of 5 average rating, 70 reviewsUnsalted Stay - Waterfront Condo
Apartment in Portage
4.92 out of 5 average rating, 25 reviewsSerenity on the Shores
Apartment in Elk Grove Village
4.95 out of 5 average rating, 57 reviewsJust remodeled apartment close to airport and mall
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
- Apartment rentals Chicago
- Apartment rentals Chicago
- Apartment rentals Downtown Chicago
- Rentals with a washing machine and dryer South Side
- Rentals with lake access South Side
- Rentals with outdoor seating South Side
- Smoking-friendly rentals South Side
- Private suite rentals South Side
- Rentals with a patio South Side
- Rentals with breakfast South Side
- Rentals with a hot tub South Side
- Fitness-friendly rentals South Side
- Rentals with a firepit South Side
- Waterfront rentals South Side
- Flat rentals South Side
- House rentals South Side
- Rentals with beach access South Side
- Pet-friendly rentals South Side
- Monthly Rentals South Side
- Rentals with pools South Side
- Townhouse rentals South Side
- Rentals with a fireplace South Side
- Family-friendly rentals South Side
- Family-friendly rentals South Side
- Rentals with an EV charger South Side
- Apartment rentals Milwaukee
- Apartment rentals Illinois
- Apartment 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