Apartment holiday rentals in South Side
Find and book unique apartments on Airbnb
Top-rated apartment rentals in South Side
Guests agree: These apartments are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for South Side apartment rentals
Weekly apartment rentals
Apartment in Pilsen Historic District
4.86 out of 5 average rating, 208 reviewsSpectacular Pilsen Studio for 2!
Apartment in Chicago
4.99 out of 5 average rating, 147 reviewsChicago Airbnb Newly Remodeled 2-Unit Apartment!
Apartment in South Lawndale
4.87 out of 5 average rating, 192 reviews2 bedroom apartment near train line and bus lines!
Apartment in Chicago
4.91 out of 5 average rating, 116 reviewsNEW Modern 2BRD apartment| 5min to McCormick Place
Apartment in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Apartment in Chicago
4.85 out of 5 average rating, 279 reviewsHUGE|3br/2ba/Near DT/Free Parking/WI-FI/Pilsen
Apartment in Little Italy
4.98 out of 5 average rating, 202 reviewsSpacious 2BR on Quiet St - Free Park/Late Checkout
Apartment in West Town
4.96 out of 5 average rating, 266 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Private apartment rentals
Apartment in Chicago
4.97 out of 5 average rating, 67 reviewsLocation! Location! Location!
Apartment in Chicago
4.93 out of 5 average rating, 54 reviewsStunning Basement Apartment w/free street parking!
Apartment in Chicago
4.91 out of 5 average rating, 74 reviewsGround-Level Speakeasy: 1BR-1.5BA Near Everything!
Apartment in Bridgeport
5.0 out of 5 average rating, 28 reviewsUrban Cottage
Apartment in Chicago
4.87 out of 5 average rating, 15 reviewsBeverly Cottage Loft
Apartment in Bridgeport
4.89 out of 5 average rating, 37 reviewsYour Perfect Spot :)-With Memory Foam Mattress!
Apartment in East Side
4.85 out of 5 average rating, 67 reviewsLovely 1-BR Apt with full kitchen & living room
Apartment in South Lawndale
5.0 out of 5 average rating, 17 reviewsFlor de Luna ~ Little Village Chicago Retreat
Apartment rentals with a hot tub
Apartment in Berwyn
4.91 out of 5 average rating, 208 reviews“Dream slice of urban homesteading.”
Apartment in West Town
4.88 out of 5 average rating, 402 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Apartment in Chicago
4.87 out of 5 average rating, 163 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Apartment in West Loop
4.87 out of 5 average rating, 107 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Apartment in Logan Square
4.92 out of 5 average rating, 37 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Apartment in The Loop
4.8 out of 5 average rating, 10 reviewsThe Areal Oasis
Apartment in Chicago
4.87 out of 5 average rating, 45 reviewsSpectacular Rooftop Getaway in Heart of City
Apartment in Chicago
5.0 out of 5 average rating, 12 reviewsLake, City, & River View Condo
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
- Apartment rentals United States
- Serviced apartment rentals United States
- Apartment rentals Chicago
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- Apartment rentals Downtown Chicago
- Condo rentals South Side
- Rentals with pools South Side
- Waterfront rentals South Side
- Rentals with breakfast South Side
- Rentals with a washing machine and dryer South Side
- Private suite rentals South Side
- Monthly Rentals South Side
- Pet-friendly rentals South Side
- Rentals with lake access South Side
- Rentals with beach access South Side
- Rentals with a fire pit South Side
- Rentals with outdoor seating South Side
- Kid-friendly rentals South Side
- Rentals with an EV charger South Side
- Smoking-friendly rentals South Side
- Rentals with a patio South Side
- Fitness-friendly rentals South Side
- House rentals South Side
- Rentals with a hot tub South Side
- Rentals with a fireplace South Side
- Family-friendly rentals South Side
- Townhouse rentals South Side
- Apartment rentals Milwaukee
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- Apartment rentals Cook County
- 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
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- Holiday Chalets United Kingdom
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- Big Cottages Australia
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- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
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- Beach Cabins United States
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