Family-friendly holiday rentals in South Side
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in South Side
Guests agree: These family-friendly homes 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 family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Chicago
4.85 out of 5 average rating, 307 reviewsLux Urban 3BR/3BA Duplex + Parking!
Loft in Chicago
4.81 out of 5 average rating, 283 reviewsArtist Loft Duplex in a 1904 Former Factory
Rental unit in Chicago
4.75 out of 5 average rating, 44 reviewsThe Professional's Playground
Condo in Chicago
4.98 out of 5 average rating, 258 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Rental unit in Chicago
4.46 out of 5 average rating, 13 reviewsSpacious 2bdm unit 15min to Dwtn
Family- and pet-friendly home rentals
Rental unit in Chicago
4.89 out of 5 average rating, 169 reviewsSpacious unique artist's home in Pilsen
Condo in Chicago
4.89 out of 5 average rating, 257 reviews2 King Bed Condo Easy Downtown Free Street Parking
Rental unit in Chicago
4.96 out of 5 average rating, 277 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Rental unit in Chicago
4.87 out of 5 average rating, 178 reviewsChicago Lincoln Park North Pond 2 Bedroom Pied-à-Terre
Home in Chicago
4.9 out of 5 average rating, 356 reviewsPrivate 3rd Floor Apartment
Guest suite in Chicago
4.97 out of 5 average rating, 272 reviewsStylish Studio in Historic Logan Square
Condo in Chicago
4.89 out of 5 average rating, 104 reviewsConvenient & Spacious 3BR Condo w/Free Parking
Guest suite in Chicago
4.95 out of 5 average rating, 149 reviewsCozy Home Living, Dogs, Kids, Free Parking, 420 OK
Family-friendly home rentals with a pool
Rental unit in Chicago
4.63 out of 5 average rating, 56 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Rental unit in Chicago
4.77 out of 5 average rating, 204 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
Guest suite in Chicago
4.96 out of 5 average rating, 82 reviewsSweet Home Chicago-9min downtown/pool/free parking
Guest suite in Berwyn
4.67 out of 5 average rating, 42 reviewsMusic Hot Spot’s Main Level
Rental unit in Chicago
4.77 out of 5 average rating, 227 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- Saugatuck Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Bend Holiday rentals
- Schaumburg Holiday rentals
- New Buffalo Holiday rentals
- Chicago Holiday rentals
- Family-friendly rentals United States
- Family-friendly rentals Chicago
- Family-friendly rentals Chicago
- Family-friendly rentals Downtown Chicago
- Condo rentals South Side
- Rentals with breakfast South Side
- Private suite rentals South Side
- Bed and breakfasts South Side
- Rentals with a washing machine and dryer South Side
- Pet-friendly rentals South Side
- Rentals with pools South Side
- Rentals with an EV charger South Side
- Rentals with outdoor seating South Side
- Waterfront rentals South Side
- Monthly Rentals South Side
- Townhouse rentals South Side
- Smoking-friendly rentals South Side
- Rentals with a fireplace South Side
- Apartment rentals South Side
- Fitness-friendly rentals South Side
- Rentals with lake access South Side
- Rentals with beach access South Side
- House rentals South Side
- Rentals with a fire pit South Side
- Rentals with a hot tub South Side
- Rentals with a patio South Side
- Kid-friendly rentals South Side
- Family-friendly rentals Illinois
- Family-friendly rentals 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