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House holiday rentals in South Side
Find and book unique houses on Airbnb
Top-rated house rentals in South Side
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for South Side house rentals
House rentals with a pool
![](https://a0.muscache.com/im/pictures/hosting/Hosting-U3RheVN1cHBseUxpc3Rpbmc6Mjk4Mjg4NjI%3D/original/b1c84404-7355-4e44-8258-d5f3492c9774.jpeg?im_w=720)
Home in Gary
4.93 out of 5 average rating, 131 reviewsBayless Dune Lodge at West Beach - Indiana Dunes!
![](https://a0.muscache.com/im/pictures/f83b9cbc-1499-406c-b48b-ffdf4075b8ec.jpg?im_w=720)
Home in Crown Point
5 out of 5 average rating, 39 reviewsLittle Pink House Downtown
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Home in Schererville
4.93 out of 5 average rating, 14 reviewsCozy house in Schererville
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Home in Schaumburg
4.92 out of 5 average rating, 13 reviewsParadise 4BR w/ Pool & Games
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Home in Cedar Lake
4.88 out of 5 average rating, 42 reviewsCheerful, Lake Home with amazing backyard!
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Home in Schaumburg
4.95 out of 5 average rating, 20 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
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Home in Bloomingdale
4.93 out of 5 average rating, 14 reviewsGiant Swimming Pool with Whole House!
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Home in Chicago
4.85 out of 5 average rating, 46 reviewsLuxury Cabin in Lakeview
Weekly house rentals
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Home in Chicago
4.97 out of 5 average rating, 30 reviewsHyde Park Haven: Exquisite Airbnb
![](https://a0.muscache.com/im/pictures/b9c72565-e466-4f00-97d9-c4efab97f003.jpg?im_w=720)
Home in Oak Park
4.96 out of 5 average rating, 85 reviewsClean, Comfy Duplex with Kitchen and Free Parking
![](https://a0.muscache.com/im/pictures/miso/Hosting-756864129367543529/original/824f1ea5-adac-4208-87e0-8aa929296630.jpeg?im_w=720)
Home in Chicago
4.98 out of 5 average rating, 53 reviewsSpacious 3 Level Home with 5 BDR/3 BA & 2 Kitchens
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Home in Chicago
5 out of 5 average rating, 63 reviewsNEW! Lake & Skyline View on Kenwood Culdesac!
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Home in Chicago
4.88 out of 5 average rating, 83 reviewsChicago getaway for two!
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Home in Munster
5 out of 5 average rating, 23 reviewsCozy Farmhouse in Munster
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Home in Chicago
4.86 out of 5 average rating, 28 reviewsLux Home Chicago 7mins Downtown
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Home in Chicago
4.93 out of 5 average rating, 46 reviewsSpacious Luxury Retreat 7 Bed Oasis with 5 Baths
Private house rentals
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Home in Chicago
4.93 out of 5 average rating, 15 reviewsModern Historic Greystone - Near Lake - Free Prkg
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Home in Munster
4.92 out of 5 average rating, 96 reviewsCozy House with Gazebo
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Home in Chicago
4.97 out of 5 average rating, 72 reviews2BD/1 BA with summer patio in quiet Roscoe Village
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Home in Chicago
4.9 out of 5 average rating, 21 reviewsModern retreat near I-94
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Home in Gary
4.94 out of 5 average rating, 68 reviewsSteps from the beach and a mile from National Park
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Home in Chicago
5 out of 5 average rating, 11 reviewsA serene haven perfect for the whole family!
![](https://a0.muscache.com/im/pictures/miso/Hosting-878104893587120556/original/b611f0ed-fe28-43a1-baad-66abf72834be.png?im_w=720)
Home in Chicago
4.92 out of 5 average rating, 36 reviewsPrivate Condo in Chicago w/ Parking, Near Evanston
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Home in Chicago
4.91 out of 5 average rating, 54 reviewsBeverly House
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