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
Get the amount of space that is right for you
Popular amenities for South Side apartment rentals
Weekly apartment rentals
Flat in McKinley Park
4.85 out of 5 average rating, 259 reviewsCharming loft style suite
15–22 Sep
Flat in Lincoln Square
4.94 out of 5 average rating, 191 reviewsSpacious, light-drenched studio-private entrance!
14–21 Jul
Flat in Chicago
4.87 out of 5 average rating, 216 reviewsGarden Apartment in the Historic Heart of the City
18–25 Oct
Flat in East Garfield Park
4.99 out of 5 average rating, 144 reviewsChicago Airbnb Newly Remodeled 2-Unit Apartment!
24 Jun – 1 Jul
Flat in Chicago
4.85 out of 5 average rating, 275 reviewsHUGE|3br/2ba/Near DT/Free Parking/WI-FI/Pilsen
23–30 Sep
Flat in Chicago
4.81 out of 5 average rating, 145 reviewsThe Posh Apt. Mins to Downtown & Hyde Park
2–9 Sep
Flat in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
3–10 Mar
Flat in Bridgeport
4.83 out of 5 average rating, 161 reviewsChicago Vintage Home
27 Sep – 4 Oct
Private apartment rentals
Flat in Chicago
4.97 out of 5 average rating, 62 reviewsLocation! Location! Location!
5–12 Jul
Flat in Chicago
4.97 out of 5 average rating, 38 reviewsVela Loft w/2 BR & Modern Design
13–20 Jan
Flat in Chicago
5.0 out of 5 average rating, 25 reviewsTravel To Chicago New City
22 Feb – 1 Mar
Flat in Chicago
4.8 out of 5 average rating, 15 reviewsTaste the Best of Chicago
7–14 Jul
Flat in Chicago
4.9 out of 5 average rating, 68 reviewsGround-Level Speakeasy: 1BR-1.5BA Near Everything!
4–11 Jul
Flat in Bridgeport
4.89 out of 5 average rating, 36 reviewsYour Perfect Spot :)-With Memory Foam Mattress!
11–18 Nov
Flat in Chicago
4.92 out of 5 average rating, 53 reviewsStunning Basement Apartment w/free street parking!
9–16 Nov
Flat in Chicago
4.95 out of 5 average rating, 22 reviewsNEW Garden Unit Close to Downtown
27 Aug – 3 Sep
Apartment rentals with a hot tub
Flat in Berwyn
4.91 out of 5 average rating, 204 reviews“Dream slice of urban homesteading.”
15–22 Oct
Flat in West Town
4.88 out of 5 average rating, 394 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
4–11 Sep
Flat in Chicago
4.91 out of 5 average rating, 32 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
20–27 Apr
Flat in Chicago
4.87 out of 5 average rating, 45 reviewsSpectacular Rooftop Getaway in Heart of City
25 Aug – 1 Sep
Flat in West Rogers Park
4.86 out of 5 average rating, 21 reviewsSpacious Beautiful Condo
22–29 Oct
Flat in The Loop
4.8 out of 5 average rating, 10 reviewsThe Areal Oasis
25 Oct – 1 Nov
Flat in Chicago
5.0 out of 5 average rating, 27 reviewsBelmont Pleasures - hot tub / arcade gaming room
7–14 Jan
Flat in West Town
4.88 out of 5 average rating, 42 reviewsCloud 9 | Presidential Penthouse Suite | The Iris
12–19 Nov
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
- Serviced apartment rentals United States
- Flat rentals United States
- Flat rentals Chicago
- Flat rentals Chicago
- Flat rentals Downtown Chicago
- Rentals with breakfast South Side
- Rentals with a washing machine and dryer South Side
- Rentals with outdoor seating South Side
- Private suite rentals South Side
- Rentals with lake access South Side
- Fitness-friendly rentals South Side
- Waterfront rentals South Side
- Rentals with a fireplace South Side
- Apartment rentals South Side
- Rentals with an EV charger South Side
- Rentals with a hot tub South Side
- Pet-friendly rentals South Side
- House rentals South Side
- Rentals with a firepit South Side
- Rentals with beach access South Side
- Family-friendly rentals South Side
- Rentals with a patio South Side
- Townhouse rentals South Side
- Family-friendly rentals South Side
- Smoking-friendly rentals South Side
- Monthly Rentals South Side
- Flat rentals Milwaukee
- Flat rentals Illinois
- Flat rentals Cook County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
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- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
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- Mansion Rentals United States
- Villa Rentals United Kingdom
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- Holiday Apartments Australia
- Holiday Houses United States
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- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
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- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
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- Luxury Dog-Friendly Cottages United Kingdom