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
Bayless Dune Lodge at West Beach - Indiana Dunes!
Home in Crown Point
Little Pink House Downtown
Home in Plainfield
Beautiful Spanish style Home (w/heated pool)
Home in Cedar Lake
Cheerful, Lake Home with amazing backyard!
Home in Schaumburg
Schaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Chicago
Luxury Cabin in Lakeview
Home in Glen Ellyn
Glen Ellyn Home
Home in Schaumburg
Paradise 4BR w/ Pool & Games
Weekly house rentals
Home in Chicago
Boho Chic Coach House 30Min to downtown W/ Parking
Home in Chicago
Free parking, close to public transit, dining
Home in Chicago
Cozy Haven
Home in Berwyn
Retro Modern Bungalow | free parking | fire pit
Home in Chicago
Spacius unit in historic gem
Home in Chicago
Beverly Cottage House
Home in Chicago
Cheerful 2 Bedroom Residential Home with Finished Basement, full kitchen and Dining Room. 2 Residential Parking passes per 24 hour stay!
Home in Chicago
Chicago Home by Midway near Downtown Attractions
Private house rentals
Home in Munster
Cozy Farmhouse in Munster
Home in Chicago
Brand New Spacious Duplex
Home in Munster
Entire home: Private, Cozy Oasis in Quiet Locale
Home in Robbins
Comfy Updated 3 Bdrm/2Bth -Near SXU, MVC & MDW
Home in Chicago
Newly Renovated Private 3BR/1BA Entire unit
Home in Calumet Park
My quaint little escape
Home in Wilmette
Unique porcelain-enamel paneled "Lustron" home
Home in Chicago
3bd/3ba Bronzeville Beauty
Destinations to explore
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