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 Highland Park
4.91 out of 5 average rating, 127 reviews2-Acre Highland Park Retreat with Heated Pool ~ 5*
Home in Plainfield
4.95 out of 5 average rating, 63 reviewsLarge Spanish style Home (w/heated pool)
Home in Crown Point
5.0 out of 5 average rating, 29 reviewsLittle Pink House Downtown
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Cedar Lake
4.86 out of 5 average rating, 35 reviewsCheerful, Lake Home with amazing backyard!
Home in Schaumburg
5.0 out of 5 average rating, 4 reviewsParadise 4BR w/ Pool & Games
Home in Chicago
4.87 out of 5 average rating, 38 reviewsLuxury Cabin in Lakeview
Weekly house rentals
Home in Chicago
4.91 out of 5 average rating, 90 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Home in Chicago
4.84 out of 5 average rating, 83 reviewsFree parking, close to public transit, dining
Home in Chicago
4.9 out of 5 average rating, 21 reviewsSpacius unit in historic gem
Home in Chicago
4.89 out of 5 average rating, 36 reviewsBrand New Spacious Duplex
Home in Berwyn
4.99 out of 5 average rating, 84 reviewsRetro Modern Bungalow | free parking | fire pit
Home in Chicago
5.0 out of 5 average rating, 15 reviewsCozy Haven
Home in Chicago
4.93 out of 5 average rating, 74 reviewsModern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
Home in Chicago
5.0 out of 5 average rating, 18 reviewsChicago Home by Midway near Downtown Attractions
Private house rentals
Home in Chicago
4.96 out of 5 average rating, 26 reviewsCharming and Classic Brick Home in Bridgeport
Home in Chicago
5.0 out of 5 average rating, 20 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, 56 reviewsNEW! Lake & Skyline View on Kenwood Culdesac!
Home in Wilmette
4.98 out of 5 average rating, 96 reviewsUnique porcelain-enamel paneled "Lustron" home
Home in Chicago
4.94 out of 5 average rating, 18 reviewsBeverly Cottage House
Home in Munster
5.0 out of 5 average rating, 17 reviewsCozy Farmhouse in Munster
Home in Robbins
4.95 out of 5 average rating, 40 reviewsComfy Updated 3 Bdrm/2Bth -Near SXU, MVC & MDW
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