Family-friendly vacation 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.
Vacation 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
4.85 out of 5 average rating, 305 reviewsLux Urban 3BR/3BA Duplex + Parking!
Loft
4.81 out of 5 average rating, 283 reviewsArtist Loft Duplex in a 1904 Former Factory
Rental unit
4.73 out of 5 average rating, 40 reviewsThe Professional's Playground
Rental unit
5 out of 5 average rating, 23 reviewsLux Loop Retreat: Amazing Views, Free Parking
Home
4.9 out of 5 average rating, 86 reviewsLOFT606: Gigantic Sunlit Former Factory Home
Condo
4.98 out of 5 average rating, 255 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Rental unit
4.55 out of 5 average rating, 11 reviewsSpacious 2bdm unit 15min to Dwtn
Rental unit
4.87 out of 5 average rating, 194 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Family- and pet-friendly home rentals
Rental unit
4.96 out of 5 average rating, 275 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Condo
4.89 out of 5 average rating, 257 reviews2 King Bed Condo Easy Downtown Free Street Parking
Rental unit
4.81 out of 5 average rating, 138 reviewsThe Biddle House (#2)
Rental unit
4.9 out of 5 average rating, 376 reviewsSunny Logan Square Artists' home
Rental unit
4.87 out of 5 average rating, 175 reviewsChicago Lincoln Park North Pond 2 Bedroom Pied-à-Terre
Guest suite
4.97 out of 5 average rating, 270 reviewsStylish Studio in Historic Logan Square
Condo
4.9 out of 5 average rating, 101 reviewsConvenient & Spacious 3BR Condo w/Free Parking
Guest suite
4.95 out of 5 average rating, 148 reviewsCozy Home Living, Dogs, Kids, Free Parking, 420 OK
Family-friendly home rentals with a pool
Rental unit
4.63 out of 5 average rating, 56 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Rental unit
4.77 out of 5 average rating, 204 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
Guest suite
4.96 out of 5 average rating, 82 reviewsSweet Home Chicago-9min downtown/pool/free parking
Guest suite
4.67 out of 5 average rating, 42 reviewsMusic Hot Spot’s Main Level
Place to stay
Beat-Town Flex Stays
Home
Sweet Home Chicago (house) - free parking, pool
Rental unit
4.77 out of 5 average rating, 225 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Destinations to explore
- Downtown Chicago Vacation rentals
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- Lake Michigan Beach Vacation rentals
- Evanston Vacation rentals
- Saugatuck Vacation rentals
- South Haven Vacation rentals
- Naperville Vacation rentals
- South Bend Vacation rentals
- Schaumburg Vacation rentals
- New Buffalo Vacation rentals
- Chicago Vacation rentals
- Family-friendly rentals United States
- Family-friendly rentals Chicago
- Family-friendly rentals Chicago
- Family-friendly rentals Downtown Chicago
- Waterfront rentals South Side
- Private suite rentals South Side
- Apartment rentals South Side
- Rentals with a washer and dryer South Side
- Rentals with breakfast South Side
- Rentals with lake access South Side
- Bed and breakfasts South Side
- Condo rentals South Side
- Rentals with outdoor seating South Side
- Monthly Rentals South Side
- Fitness-friendly rentals South Side
- Rentals with a fireplace South Side
- Rentals with an EV charger South Side
- Smoking-friendly rentals South Side
- Rentals with a patio South Side
- Rentals with beach access South Side
- Rentals with pools South Side
- Rentals with a fire pit South Side
- Pet-friendly rentals South Side
- Kid-friendly rentals South Side
- Rentals with a hot tub South Side
- Townhouse rentals South Side
- House 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