House holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in South Side
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 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, 30 reviewsLittle Pink House Downtown
Home in Schaumburg
4.33 out of 5 average rating, 6 reviewsParadise 4BR w/ Pool & Games
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
Weekly house rentals
Home in Chicago
4.85 out of 5 average rating, 84 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
5.0 out of 5 average rating, 28 reviews3bd/3ba Bronzeville Beauty
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
4.9 out of 5 average rating, 31 reviewsCheerful 3 Bedroom, City Oasis
Home in Chicago
5.0 out of 5 average rating, 19 reviewsChicago Home by Midway near Downtown Attractions
Home in Chicago
4.94 out of 5 average rating, 18 reviewsBeverly Cottage House
Private house rentals
Home in Chicago
4.95 out of 5 average rating, 21 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, 46 reviewsSpacious 3 Level Home with 5 BDR/3 BA & 2 Kitchens
Home in Chicago
4.89 out of 5 average rating, 36 reviewsBrand New Spacious Duplex
Home in Chicago
5.0 out of 5 average rating, 12 reviewsModern retreat near I-94
Home in Calumet Park
4.93 out of 5 average rating, 27 reviewsMy quaint little escape
Home in Munster
5.0 out of 5 average rating, 18 reviewsCozy Farmhouse in Munster
Home in Chicago Ridge
4.88 out of 5 average rating, 59 reviewsQuiet cul-de-sac with huge fenced in backyard
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Schaumburg Holiday rentals
- Chicago Holiday rentals
- Lighthouse rentals United States
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- Earth house rentals United States
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- Lakehouse rentals Chicago
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- House rentals Chicago
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- Lakehouse rentals Chicago
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- House rentals Chicago
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- Townhouse rentals Downtown Chicago
- House rentals Downtown Chicago
- Rentals with a washing machine and dryer South Side
- Rentals with lake access South Side
- Apartment rentals South Side
- Rentals with outdoor seating South Side
- Smoking-friendly rentals South Side
- Private suite rentals South Side
- Rentals with a patio South Side
- Rentals with breakfast South Side
- Rentals with a hot tub South Side
- Fitness-friendly rentals South Side
- Rentals with a firepit South Side
- Waterfront rentals South Side
- Flat rentals South Side
- Rentals with beach access South Side
- Pet-friendly rentals South Side
- Monthly Rentals South Side
- Rentals with pools South Side
- Townhouse rentals South Side
- Rentals with a fireplace South Side
- Family-friendly rentals South Side
- Family-friendly rentals South Side
- Rentals with an EV charger South Side
- House rentals Milwaukee
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- Tiny house rentals Illinois
- House rentals Illinois
- Guest house rentals Illinois
- Treehouse rentals Illinois
- Townhouse rentals Illinois
- Lakehouse rentals Illinois
- House rentals Cook County
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- Yurt Rentals United States
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- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
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- Holiday Apartments Australia
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- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom