House vacation rentals in South Side
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Top-rated house rentals in South Side
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation 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
Home in Crown Point
5.0 out of 5 average rating, 25 reviewsLittle Pink House Downtown
Sep 14 – 21
Home in Cedar Lake
4.85 out of 5 average rating, 34 reviewsCheerful, Lake Home with amazing backyard!
Mar 10 – 17
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Dec 8 – 15
Home in Chicago
4.86 out of 5 average rating, 37 reviewsLuxury Cabin in Lakeview
Jul 7 – 14
Home in Glen Ellyn
4.94 out of 5 average rating, 16 reviewsGlen Ellyn Home
Jul 23 – 30
Home in Schaumburg
New place to stayParadise 4BR w/ Pool & Games
Nov 30 – Dec 7
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
Aug 15 – 22
Home in Gary
4.82 out of 5 average rating, 213 reviewsOasis , Near Beach, Hard Rock and Dunes
Jun 7 – 14
Weekly house rentals
Home in Chicago Ridge
4.9 out of 5 average rating, 51 reviewsQuiet cul-de-sac with huge fenced in backyard
Nov 27 – Dec 4
Home in Calumet Park
4.95 out of 5 average rating, 22 reviewsMy quaint little escape
Sep 22 – 29
Home in Chicago
5.0 out of 5 average rating, 15 reviewsCozy Haven
Nov 28 – Dec 5
Home in Chicago
4.89 out of 5 average rating, 35 reviewsBrand New Spacious Duplex
Sep 13 – 20
Home in Lansing
4.8 out of 5 average rating, 66 reviewsThe Walter Experience
Sep 5 – 12
Home in Whiting
5.0 out of 5 average rating, 16 reviewsChicago Close 2 King 1 Full Mini Golf House
Feb 27 – Mar 6
Home in Chicago
5.0 out of 5 average rating, 47 reviewsCozy, Quiet, Riverwalk Sanctuary
Nov 9 – 16
Home in Chicago
5.0 out of 5 average rating, 13 reviewsModern Family Townhouse
Dec 26 – Jan 2
Private house rentals
Home in Munster
4.97 out of 5 average rating, 35 reviewsEntire home: Private, Cozy Oasis in Quiet Locale
Mar 28 – Apr 4
Home in Munster
5.0 out of 5 average rating, 13 reviewsCozy Farmhouse in Munster
Jun 7 – 14
Home in Chicago
5.0 out of 5 average rating, 41 reviewsSpacious 3 Level Home with 5 BDR/3 BA & 2 Kitchens
Apr 16 – 23
Home in Chicago
5.0 out of 5 average rating, 53 reviewsNEW! Lake & Skyline View on Kenwood Culdesac!
Jul 21 – 28
Home in Chicago
5.0 out of 5 average rating, 8 reviewsModern Historic Greystone - Near Lake - Free Prkg
Nov 8 – 15
Home in Chicago
4.9 out of 5 average rating, 29 reviewsCheerful 3 Bedroom, City Oasis
Jan 19 – 26
Home in Chicago
4.93 out of 5 average rating, 71 reviewsModern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
Nov 21 – 28
Home in Chicago
5.0 out of 5 average rating, 9 reviewsModern retreat near I-94
Oct 16 – 23
Destinations to explore
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