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.
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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 favourite
Home in Pilsen Historic District
4.95 out of 5 average rating, 328 reviewsGet Cozy at a Powder-Blue Residence in the Heart of Pilsen
Guest favourite
Apartment in Bridgeport
4.89 out of 5 average rating, 301 reviewsVintage Bridgeport Apartment
Superhost
Apartment in Woodlawn
4.83 out of 5 average rating, 155 reviewsUniversity Retreat
Guest favourite
Guest suite in Hyde Park
4.92 out of 5 average rating, 198 reviewsConvenient Hyde Park 2 Bedroom Apartment
Superhost
Guest suite in Chicago
4.9 out of 5 average rating, 171 reviewsChicago Living: Your Home Away From Home
Guest favourite
Cottage in Gary
4.97 out of 5 average rating, 120 reviewsNeon Dunes Vista Beachfront Cottage
Guest favourite
Apartment in Chicago
4.97 out of 5 average rating, 67 reviewsLocation! Location! Location!
Guest favourite
Vacation home in Chicago
4.96 out of 5 average rating, 45 reviewsUChicago Luxurious King Suite Lakefront
Destinations to explore
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- Rentals with a washer and dryer South Side
- Rentals with lake access South Side
- Condo rentals 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
- Apartment rentals South Side
- House rentals South Side
- Rentals with beach access South Side
- Pet-friendly rentals South Side
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- Townhouse rentals South Side
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- Family-friendly rentals South Side
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- Rentals with an EV charger South Side
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