Vacation rentals in South Side
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Top-rated vacation rentals in South Side
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Vacation rentals for every style
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Popular amenities for South Side vacation rentals
Other great vacation rentals in South Side
Guest favorite
Apartment in Woodlawn
4.83 out of 5 average rating, 154 reviewsUniversity Retreat
Guest favorite
Guest suite in Chicago
4.93 out of 5 average rating, 40 reviewsClassic Den @ U Chicago
Guest favorite
Guesthouse in Kenwood
4.88 out of 5 average rating, 17 reviewsLuxe Loft studio - Great location!
Guest favorite
Vacation home in South Shore
4.95 out of 5 average rating, 41 reviewsUChicago Luxurious King Suite Lakefront
Guest favorite
Apartment in Woodlawn
5.0 out of 5 average rating, 6 reviewsRenovated Retreat near U of Chicago
Superhost
Apartment in Hyde Park
5.0 out of 5 average rating, 3 reviewsModern 1BR Chicago Hideaway
Guest favorite
Apartment in Chicago
4.97 out of 5 average rating, 60 reviewsLocation! Location! Location!
Guest favorite
Apartment in Chicago
5.0 out of 5 average rating, 23 reviewsTravel To Chicago New City
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- Rentals with a patio South Side
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