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, 31 reviewsLittle Pink House Downtown
Home in Plainfield
4.95 out of 5 average rating, 64 reviewsUnique 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
4.86 out of 5 average rating, 36 reviewsCheerful, Lake Home with amazing backyard!
Home in Chicago
4.87 out of 5 average rating, 39 reviewsLuxury Cabin in Lakeview
Home in Schaumburg
5.0 out of 5 average rating, 6 reviewsParadise 4BR w/ Pool & Games
Home in Glen Ellyn
4.94 out of 5 average rating, 18 reviewsGlen Ellyn Home
Weekly house rentals
Home in Joliet
4.84 out of 5 average rating, 164 reviewsCozy Private Cottage in the Cathedral District
Home in Chicago
4.96 out of 5 average rating, 208 reviewsDivision St Designer Home In Heart of Wicker Park
Home in Chicago
4.98 out of 5 average rating, 179 reviewsThe Evergreen House
Home in Chicago
4.91 out of 5 average rating, 93 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Home in Chicago
5.0 out of 5 average rating, 17 reviewsCozy Haven
Home in Lansing
4.82 out of 5 average rating, 74 reviewsJune at the Walter
Home in Chicago
4.89 out of 5 average rating, 36 reviewsBrand New Spacious Duplex
Home in Chicago Ridge
4.89 out of 5 average rating, 63 reviewsQuiet cul-de-sac with huge fenced in backyard
Private house rentals
Home in Chicago
5.0 out of 5 average rating, 21 reviewsChicago Home by Midway near Downtown Attractions
Home in Palos Hills
4.92 out of 5 average rating, 13 reviewsCozy lower level in Palos Hills
Home in Munster
5.0 out of 5 average rating, 19 reviewsCozy Farmhouse in Munster
Home in Chicago
4.97 out of 5 average rating, 31 reviewsLakeview Condo
Home in Chicago
5.0 out of 5 average rating, 56 reviewsCozy, Quiet, Riverwalk Sanctuary
Home in Munster
4.95 out of 5 average rating, 42 reviewsEntire home: Private, Cozy Oasis in Quiet Locale
Home in Chicago
4.8 out of 5 average rating, 5 reviewsNewly Renovated Private 3BR/1BA Entire unit
Home in Chicago
4.86 out of 5 average rating, 73 reviewsChicago getaway for two!
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- Family travel hub Tips and inspiration
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- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
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