Vacation rentals with outdoor seating in South Side
Find and book unique outdoor seating rentals on Airbnb
Top-rated outdoor seating rentals in South Side
Guests agree: these outdoor seating rentals 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 outdoor seating rentals
House rentals with outdoor seating
Home in Chicago
4.95 out of 5 average rating, 171 reviewsParadise on the Park
Jan 2 – 9
Home in Berwyn
4.92 out of 5 average rating, 240 reviewsPrivate apartment with retro vibe
Sep 8 – 15
Home in Chicago
4.98 out of 5 average rating, 206 reviewsWrigleyville Southport Studio
Nov 22 – 29
Home in Whiting
4.83 out of 5 average rating, 121 reviewsThe Spa of Downtown Whiting
Apr 4 – 11
Home in Chicago
4.97 out of 5 average rating, 357 reviewsGreystone Haven in Logan Square
Oct 17 – 24
Home in Montgomery
4.84 out of 5 average rating, 109 reviewsNice, Private Ranch Home
Oct 20 – 27
Home in Forest Park
4.91 out of 5 average rating, 223 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
Jun 23 – 30
Home in Chicago
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
Dec 18 – 25
Apartment rentals with outdoor seating
Apartment in Blue Island
4.93 out of 5 average rating, 265 reviewsCharming Unique 2 Bdrm Apartment in Victorian Home
Dec 24 – 31
Apartment in Chicago
4.98 out of 5 average rating, 199 reviewsSpacious 2BR on Quiet St - Free Park/Late Checkout
Jan 4 – 11
Apartment in Forest Park
5.0 out of 5 average rating, 222 reviewsLike a Treehouse!
Oct 24 – 31
Apartment in Chicago
4.97 out of 5 average rating, 118 reviewsDesigner Avondale Attic
Jul 22 – 29
Apartment in Chicago
4.89 out of 5 average rating, 473 reviewsiKlektik House Chicago / Robin
Sep 22 – 29
Apartment in Chicago
4.96 out of 5 average rating, 323 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
Dec 18 – 25
Apartment in Chicago
4.95 out of 5 average rating, 109 reviewsComfortable, modern apartment 20 Min from Downtown
Mar 8 – 15
Apartment in Chicago
4.99 out of 5 average rating, 104 reviewsNewly Renovated, Spacious 2BR in Andersonville
Dec 7 – 14
Condo rentals with outdoor seating
Condo in Chicago
4.9 out of 5 average rating, 136 reviewsEast Garfield Park 2 Bedroom
Nov 16 – 23
Condo in Chicago
4.96 out of 5 average rating, 120 reviewsPrivate hot tub - King bed suite - Free parking
Jun 25 – Jul 2
Condo in Chicago
4.98 out of 5 average rating, 234 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Mar 18 – 25
Condo in Chicago
5.0 out of 5 average rating, 100 reviewsSpacious 4 Bedroom Condo
Feb 11 – 18
Condo in Chicago
4.88 out of 5 average rating, 235 reviews2 King Bed Condo Easy Downtown Free Street Parking
Jan 29 – Feb 5
Condo in Chicago
4.91 out of 5 average rating, 121 reviewsSpacious & Modern Family Friendly North Center Apt
Feb 12 – 19
Condo in Chicago
4.88 out of 5 average rating, 136 reviews1 #11 - 2 Bedroom 1 Bath Condo - McCormick Place
Jan 22 – 29
Condo in Chicago
4.81 out of 5 average rating, 265 reviewsWelcoming 2BR in Chicago's Best Neighborhood!
Jun 27 – Jul 4
Destinations to explore
- Downtown Chicago Vacation rentals
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- Lake Michigan Beach Vacation rentals
- Saugatuck Vacation rentals
- Evanston Vacation rentals
- South Haven Vacation rentals
- Naperville Vacation rentals
- South Bend Vacation rentals
- New Buffalo Vacation rentals
- Schaumburg Vacation rentals
- Chicago Vacation rentals
- Rentals with outdoor seating United States
- Rentals with outdoor seating Chicago
- Rentals with outdoor seating Chicago
- Rentals with outdoor seating Downtown Chicago
- Rentals with breakfast South Side
- Family-friendly rentals South Side
- Rentals with an EV charger South Side
- Rentals with a washer and dryer South Side
- Rentals with a fireplace South Side
- Smoking-friendly rentals South Side
- Condo rentals South Side
- Private suite rentals South Side
- Rentals with a patio South Side
- Rentals with a hot tub South Side
- Rentals with a fire pit South Side
- Kid-friendly rentals South Side
- Rentals with beach access South Side
- Townhouse rentals South Side
- Fitness-friendly rentals South Side
- House rentals South Side
- Apartment rentals South Side
- Waterfront rentals South Side
- Monthly Rentals South Side
- Rentals with lake access South Side
- Pet-friendly rentals South Side
- Rentals with outdoor seating Milwaukee
- Rentals with outdoor seating Illinois
- Rentals with outdoor seating Cook County
- 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