Condo holiday rentals in South Side
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Top-rated condo rentals in South Side
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Popular amenities for South Side condo rentals
Weekly condo rentals
Condo in Chicago
5.0 out of 5 average rating, 107 reviewsSpacious 4 Bedroom Condo
Condo in Chicago
4.96 out of 5 average rating, 112 reviewsCHIC DOWNTOWN PENTHOUSE w/ private roof +parking
Condo in Chinatown
4.83 out of 5 average rating, 162 reviewsSecluded 2BR APT in Chinatown by McCormick/DWTN
Condo in Chicago
4.87 out of 5 average rating, 110 reviewsSpacious Duplex in Great Location
Condo in Chicago
4.91 out of 5 average rating, 124 reviewsSpacious & Modern Family Friendly North Center Apt
Condo in Chicago
4.9 out of 5 average rating, 139 reviewsEast Garfield Park 2 Bedroom
Condo in Chicago
4.87 out of 5 average rating, 441 reviewsHumboldt Park Traveler's Lodge
Condo in Chicago
4.88 out of 5 average rating, 239 reviews2 King Bed Condo Easy Downtown Free Street Parking
Pet-friendly condo rentals
Condo in Evanston
4.76 out of 5 average rating, 573 reviewsSpacious Evanston Unit - Walk to Northwestern U
Condo in Chicago
4.99 out of 5 average rating, 221 reviews❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D
Condo in Chicago
4.93 out of 5 average rating, 192 reviewsPvt 1bdr Rogers Park, Loyola, Northwestern.
Condo in Chicago
4.95 out of 5 average rating, 132 reviewsThe Grand Kimball Lodge, Logan Square, Sleeps 14
Condo in Chicago
4.82 out of 5 average rating, 119 reviewsCharming Condo near U.C./Loop/McCormick Place
Condo in Chicago
4.83 out of 5 average rating, 313 reviewsChic and Charming Vintage Condominium in Lincoln Park
Condo in Chicago
4.78 out of 5 average rating, 203 reviewsModern Luxury In Old Town - Sleeps 4
Condo in The Loop
4.8 out of 5 average rating, 171 reviewsMICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
Condo rentals with a pool
Condo in Chicago
4.74 out of 5 average rating, 152 reviewsCentral Downtown Location-Modern 2BR Condo
Condo in Evanston
4.91 out of 5 average rating, 105 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Condo in Portage
4.93 out of 5 average rating, 82 reviewsCozy 1 bedroom condo on Marina near Lake Michigan
Condo in Lisle
4.92 out of 5 average rating, 48 reviewsPeaceful Condo in Lisle, Illinois
Condo in Elk Grove Village
4.95 out of 5 average rating, 57 reviewsJust remodeled apartment close to airport and mall
Condo in Portage
5.0 out of 5 average rating, 56 reviewsLuxury Waterfront 2 Bedroom Condo by Lake Michigan
Condo in Portage
4.92 out of 5 average rating, 25 reviewsSerenity on the Shores
Condo in Portage
4.92 out of 5 average rating, 73 reviewsUnsalted Stay - Waterfront 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
- Condo rentals Chicago
- Condo rentals Chicago
- Condo rentals Downtown Chicago
- Family-friendly rentals South Side
- Rentals with a washing machine and dryer South Side
- Apartment rentals South Side
- Private suite rentals South Side
- Rentals with lake access South Side
- Waterfront rentals South Side
- Rentals with a patio South Side
- Rentals with outdoor seating South Side
- Rentals with breakfast South Side
- Rentals with a fire pit South Side
- Rentals with beach access South Side
- Smoking-friendly rentals South Side
- Pet-friendly rentals South Side
- Rentals with a fireplace South Side
- Monthly Rentals South Side
- Rentals with pools South Side
- Kid-friendly rentals South Side
- Rentals with an EV charger South Side
- Rentals with a hot tub South Side
- Townhouse rentals South Side
- Fitness-friendly rentals South Side
- House rentals South Side
- Condo rentals Milwaukee
- Condo rentals Illinois
- Condo rentals Cook County
- Yurt Rentals United States
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- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
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- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
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- Holiday Chalets United Kingdom
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- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
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- Holiday Apartments Australia
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- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
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- 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
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