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, 127 reviewsBayless Dune Lodge at West Beach - Indiana Dunes!
Home in Crown Point
5.0 out of 5 average rating, 30 reviewsLittle Pink House Downtown
Home in Plainfield
4.95 out of 5 average rating, 63 reviewsLarge Spanish style Home (w/heated pool)
Home in Cedar Lake
4.86 out of 5 average rating, 36 reviewsCheerful, Lake Home with amazing backyard!
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Chicago
4.87 out of 5 average rating, 39 reviewsLuxury Cabin in Lakeview
Home in Glen Ellyn
4.94 out of 5 average rating, 17 reviewsGlen Ellyn Home
Home in Schaumburg
4.33 out of 5 average rating, 6 reviewsParadise 4BR w/ Pool & Games
Weekly house rentals
Home in Chicago
4.78 out of 5 average rating, 18 reviewsCozy 2 bed Condo in Bronzeville!
Home in Chicago
4.85 out of 5 average rating, 84 reviewsFree parking, close to public transit, dining
Home in Chicago
5.0 out of 5 average rating, 17 reviewsCozy Haven
Home in Berwyn
4.99 out of 5 average rating, 84 reviewsRetro Modern Bungalow | free parking | fire pit
Home in Chicago Ridge
4.88 out of 5 average rating, 60 reviewsQuiet cul-de-sac with huge fenced in backyard
Home in Chicago
4.9 out of 5 average rating, 31 reviewsCheerful 2 Bedroom Residential Home with Finished Basement, full kitchen and Dining Room. 2 Residential Parking passes per 24 hour stay!
Home in Chicago
5.0 out of 5 average rating, 12 reviewsModern retreat near I-94
Home in Chicago
4.94 out of 5 average rating, 18 reviewsBeverly Cottage House
Private house rentals
Home in Chicago
5.0 out of 5 average rating, 54 reviewsCozy, Quiet, Riverwalk Sanctuary
Home in Chicago
4.86 out of 5 average rating, 70 reviewsChicago getaway for two!
Home in Chicago
4.89 out of 5 average rating, 36 reviewsBrand New Spacious Duplex
Home in Lansing
4.82 out of 5 average rating, 71 reviews-:The Walter-:
Home in Chicago
5.0 out of 5 average rating, 15 reviewsModern Family Townhouse
Home in Chicago
4.9 out of 5 average rating, 31 reviewsCheerful 3 Bedroom, City Oasis
Home in Calumet Park
4.93 out of 5 average rating, 27 reviewsMy quaint little escape
Home in Chicago
4.98 out of 5 average rating, 59 reviews2BD/1 BA with summer patio in quiet Roscoe Village
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- Family travel hub Tips and inspiration
- Family budget travel Get there for less
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- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes