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 Gary
4.93 out of 5 average rating, 126 reviewsBayless Dune Lodge at West Beach - Indiana Dunes!
Home in Crown Point
5.0 out of 5 average rating, 26 reviewsLittle Pink House Downtown
Home in Plainfield
4.95 out of 5 average rating, 63 reviewsLarge Spanish style Home (w/heated pool)
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Cedar Lake
4.85 out of 5 average rating, 34 reviewsCheerful, Lake Home with amazing backyard!
Home in Schaumburg
5.0 out of 5 average rating, 3 reviewsParadise 4BR w/ Pool & Games
Home in Chicago
4.86 out of 5 average rating, 37 reviewsLuxury Cabin in Lakeview
Home in Lake Forest
4.91 out of 5 average rating, 58 reviewsBeautiful 137 Year Old Farm Home (3night min)
Weekly house rentals
Home in Chicago
4.91 out of 5 average rating, 89 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Home in Chicago
4.9 out of 5 average rating, 20 reviewsSpacius unit in historic gem
Home in Chicago
4.84 out of 5 average rating, 83 reviewsFree parking, close to public transit, dining
Home in Chicago
5.0 out of 5 average rating, 15 reviewsCozy Haven
Home in Calumet Park
4.92 out of 5 average rating, 25 reviewsMy quaint little escape
Home in Chicago
5.0 out of 5 average rating, 13 reviewsModern Family Townhouse
Home in Chicago
4.9 out of 5 average rating, 30 reviewsCheerful 3 Bedroom, City Oasis
Home in Chicago
5.0 out of 5 average rating, 17 reviewsChicago Home by Midway near Downtown Attractions
Private house rentals
Home in Chicago
5.0 out of 5 average rating, 19 reviewsHyde Park Haven: Exquisite Airbnb
Home in Chicago
5.0 out of 5 average rating, 8 reviewsModern Historic Greystone - Near Lake - Free Prkg
Home in Chicago
5.0 out of 5 average rating, 43 reviewsSpacious 3 Level Home with 5 BDR/3 BA & 2 Kitchens
Home in Munster
5.0 out of 5 average rating, 17 reviewsCozy Farmhouse in Munster
Home in Munster
4.95 out of 5 average rating, 38 reviewsEntire home: Private, Cozy Oasis in Quiet Locale
Home in Chicago
4.89 out of 5 average rating, 36 reviewsBrand New Spacious Duplex
Home in Chicago
4.94 out of 5 average rating, 18 reviewsBeverly Cottage House
Home in Chicago
4.96 out of 5 average rating, 25 reviewsCharming and Classic Brick Home in Bridgeport
Destinations to explore
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