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 Gary
4.93 out of 5 average rating, 126 reviewsBayless Dune Lodge at West Beach - Indiana Dunes!
Dec 21 – 28
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!
Oct 18 – 25
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Aug 17 – 24
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
5.0 out of 5 average rating, 3 reviewsParadise 4BR w/ Pool & Games
Nov 12 – 19
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
Jul 18 – 25
Weekly house rentals
Home in Chicago Ridge
4.9 out of 5 average rating, 52 reviewsQuiet cul-de-sac with huge fenced in backyard
Mar 7 – 14
Home in Chicago
5.0 out of 5 average rating, 15 reviewsCozy Haven
Sep 16 – 23
Home in Chicago
4.89 out of 5 average rating, 35 reviewsBrand New Spacious Duplex
Sep 14 – 21
Home in Calumet Park
4.95 out of 5 average rating, 22 reviewsMy quaint little escape
Sep 27 – Oct 4
Home in Berwyn
5.0 out of 5 average rating, 77 reviewsRetro Modern Bungalow | free parking | fire pit
Nov 3 – 10
Home in Chicago
5.0 out of 5 average rating, 13 reviewsModern Family Townhouse
Dec 26 – Jan 2
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, 15 reviewsChicago Home by Midway near Downtown Attractions
Oct 19 – 26
Private house rentals
Home in Chicago
5.0 out of 5 average rating, 8 reviewsModern Historic Greystone - Near Lake - Free Prkg
Nov 8 – 15
Home in Munster
5.0 out of 5 average rating, 13 reviewsCozy Farmhouse in Munster
Jun 7 – 14
Home in Chicago
4.9 out of 5 average rating, 29 reviewsCheerful 3 Bedroom, City Oasis
Jan 6 – 13
Home in Chicago
5.0 out of 5 average rating, 41 reviewsSpacious 3 Level Home with 5 BDR/3 BA & 2 Kitchens
Nov 30 – Dec 7
Home in Lansing
4.8 out of 5 average rating, 66 reviewsThe Walter Experience
Oct 13 – 20
Home in Chicago
4.93 out of 5 average rating, 71 reviewsModern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
Aug 15 – 22
Home in Chicago
4.96 out of 5 average rating, 23 reviewsCharming and Classic Brick Home in Bridgeport
Oct 16 – 23
Home in Wilmette
4.98 out of 5 average rating, 92 reviewsUnique porcelain-enamel paneled "Lustron" home
Sep 11 – 18
Destinations to explore
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