Holiday rentals in South Side
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in South Side
Guests agree: these stays are highly rated for location, cleanliness and more.
0 of 0 items showing
1 of 3 pages
1 of 3 pages
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for South Side holiday rentals
Other great holiday rentals in South Side
Guest favourite
Flat in Bridgeport
4.89 out of 5 average rating, 301 reviewsVintage Bridgeport Apartment
Guest favourite
Flat in Pilsen Historic District
4.89 out of 5 average rating, 245 reviewsModern
Guest favourite
Guest suite in Chicago
4.93 out of 5 average rating, 40 reviewsClassic Den @ U Chicago
Guest favourite
Holiday home in Chicago
4.95 out of 5 average rating, 43 reviewsUChicago Luxurious King Suite Lakefront
Guest favourite
Flat in Chicago
5.0 out of 5 average rating, 28 reviewsTravel To Chicago New City
Guest favourite
Home in Mount Greenwood
4.91 out of 5 average rating, 89 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Guest favourite
Flat in Chicago
4.9 out of 5 average rating, 69 reviewsGround-Level Speakeasy: 1BR-1.5BA Near Everything!
Guest favourite
Flat in Chicago
4.97 out of 5 average rating, 64 reviewsLocation! Location! Location!
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
- Waterfront rentals South Side
- Rentals with outdoor seating South Side
- Flat rentals South Side
- Rentals with lake access South Side
- Rentals with a washing machine and dryer South Side
- Pet-friendly rentals South Side
- Apartment rentals South Side
- Townhouse rentals South Side
- Family-friendly rentals South Side
- Rentals with an EV charger South Side
- Fitness-friendly rentals South Side
- Rentals with a fireplace South Side
- Rentals with breakfast South Side
- Rentals with a patio South Side
- Rentals with beach access South Side
- Family-friendly rentals South Side
- Rentals with a firepit South Side
- House rentals South Side
- Rentals with a hot tub South Side
- Private suite rentals South Side
- Monthly Rentals South Side
- Smoking-friendly rentals South Side
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- 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
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- 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
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom