House vacation 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.
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 Highland Park
4.9 out of 5 average rating, 125 reviews2-Acre Highland Park Retreat with Heated Pool ~ 5*
Apr 16 – 23
Home in Gary
4.93 out of 5 average rating, 125 reviewsBayless Dune Lodge at West Beach - Indiana Dunes!
Jun 21 – 28
Home in Crown Point
5.0 out of 5 average rating, 25 reviewsLittle Pink House Downtown
Oct 16 – 23
Home in Plainfield
4.95 out of 5 average rating, 62 reviewsLarge Spanish style Home (w/heated pool)
Aug 5 – 12
Home in Cedar Lake
4.85 out of 5 average rating, 34 reviewsCheerful, Lake Home with amazing backyard!
Oct 14 – 21
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
May 25 – Jun 1
Home in Chicago
4.86 out of 5 average rating, 36 reviewsLuxury Cabin in Lakeview
Jul 7 – 12
Home in Glen Ellyn
4.94 out of 5 average rating, 16 reviewsGlen Ellyn Home
Jul 23 – 30
Weekly house rentals
Home in Chicago
4.96 out of 5 average rating, 200 reviewsDivision St Designer Home In Heart of Wicker Park
May 20 – 25
Home in Chicago
5.0 out of 5 average rating, 15 reviewsCozy Haven
Jun 4 – 11
Home in Chicago Ridge
4.9 out of 5 average rating, 50 reviewsQuiet cul-de-sac with huge fenced in backyard
Nov 24 – Dec 1
Home in Chicago
4.84 out of 5 average rating, 81 reviewsFree parking, close to public transit, dining
May 23 – 30
Home in Chicago
4.89 out of 5 average rating, 35 reviewsBrand New Spacious Duplex
Oct 8 – 15
Home in Calumet Park
4.95 out of 5 average rating, 22 reviewsMy quaint little escape
Oct 15 – 22
Home in Lansing
4.85 out of 5 average rating, 65 reviewsThe Walter Experience(2bd 1ba) April special
Aug 13 – 20
Home in Chicago
5.0 out of 5 average rating, 13 reviewsModern Family Townhouse
Dec 26 – Jan 2
Private house rentals
Home in Chicago
4.93 out of 5 average rating, 70 reviewsModern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
Nov 8 – 15
Home in Chicago
5.0 out of 5 average rating, 52 reviewsNEW! Lake & Skyline View on Kenwood Culdesac!
Aug 14 – 21
Home in Chicago
4.86 out of 5 average rating, 14 reviewsGarden Apartment in Gated Home
Mar 9 – 16
Home in Chicago
5.0 out of 5 average rating, 41 reviewsSpacious 3 Level Home with 5 BDR/3 BA & 2 Kitchens
Apr 4 – 11
Home in Chicago
5.0 out of 5 average rating, 18 reviewsHyde Park Haven: Exquisite Airbnb
Sep 25 – Oct 2
Home in Chicago
4.92 out of 5 average rating, 12 reviewsBeverly Cottage House
Oct 17 – 24
Home in Chicago
4.9 out of 5 average rating, 29 reviewsCheerful 3 Bedroom, City Oasis
Nov 16 – 23
Home in Chicago
4.92 out of 5 average rating, 12 reviewsExperience Chicago from Our 3-Story Retreat
Jan 7 – 14
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- Family travel hub Tips and inspiration
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