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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
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Guest favourite
Guesthouse in Chicago
4.85 out of 5 average rating, 87 reviewsThe Ultimate Eco-Friendly Tiny House Experience!
![](https://a0.muscache.com/im/pictures/miso/Hosting-842816582493215704/original/2adbb2a7-6708-4e9d-81dc-d54e30bfe6ef.jpeg?im_w=720)
Guest favourite
Rental unit in Chicago
4.89 out of 5 average rating, 46 reviewsYour Perfect Spot :)-With Memory Foam Mattress!
![](https://a0.muscache.com/im/pictures/miso/Hosting-760985260337363062/original/22243a64-61dd-414d-9bb4-e110ef9afb2b.jpeg?im_w=720)
Guest favourite
Rental unit in Chicago
4.95 out of 5 average rating, 65 reviewsSpacious 1BR Garden Apt & Parking
![](https://a0.muscache.com/im/pictures/hosting/Hosting-1044908124687074157/original/0e5327c5-3af6-4dd7-aa52-89b2a67ac625.jpeg?im_w=720)
Guest favourite
Home in Chicago
4.93 out of 5 average rating, 28 reviewsSpacius unit in historic gem
![](https://a0.muscache.com/im/pictures/miso/Hosting-770523073506526538/original/b5b6bebb-b768-40f1-971b-7b89340a9899.jpeg?im_w=720)
Guest favourite
Rental unit in Chicago
4.92 out of 5 average rating, 84 reviewsGround-Level Speakeasy: 1BR-1.5BA Near Everything!
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Guest favourite
Rental unit in Chicago
4.92 out of 5 average rating, 24 reviewsBeverly Cottage Loft
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Guest favourite
Guest suite in Chicago
4.89 out of 5 average rating, 80 reviewsPRIVATE 2-bedroom 1.5 bath w/ living room
![](https://a0.muscache.com/im/pictures/miso/Hosting-797366668806692109/original/a8b25591-9fb2-499b-a2d0-8a5b3daabf49.jpeg?im_w=720)
Superhost
Rental unit in Chicago
4.9 out of 5 average rating, 72 reviewsEclipse: Apt. in Woodlawn | Near UChicago
Destinations to explore
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- Waterfront rentals South Side
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