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 in Chicago
4.85 out of 5 average rating, 305 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
4.73 out of 5 average rating, 40 reviewsThe Professional's Playground
Rental unit in Chicago
5 out of 5 average rating, 23 reviewsLux Loop Retreat: Amazing Views, Free Parking
Home in Chicago
4.9 out of 5 average rating, 86 reviewsLOFT606: Gigantic Sunlit Former Factory Home
Condo in Chicago
4.98 out of 5 average rating, 255 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Rental unit in Chicago
4.55 out of 5 average rating, 11 reviewsSpacious 2bdm unit 15min to Dwtn
Rental unit in Chicago
4.87 out of 5 average rating, 194 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Family- and pet-friendly home rentals
Rental unit in Chicago
4.96 out of 5 average rating, 275 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Condo in Chicago
4.89 out of 5 average rating, 257 reviews2 King Bed Condo Easy Downtown Free Street Parking
Rental unit in Chicago
4.81 out of 5 average rating, 138 reviewsThe Biddle House (#2)
Rental unit in Chicago
4.9 out of 5 average rating, 376 reviewsSunny Logan Square Artists' home
Rental unit in Chicago
4.87 out of 5 average rating, 175 reviewsChicago Lincoln Park North Pond 2 Bedroom Pied-à-Terre
Guest suite in Chicago
4.97 out of 5 average rating, 270 reviewsStylish Studio in Historic Logan Square
Condo in Chicago
4.9 out of 5 average rating, 101 reviewsConvenient & Spacious 3BR Condo w/Free Parking
Guest suite in Chicago
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 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
Place to stay in Berwyn
Beat-Town Flex Stays
Home in Chicago
Sweet Home Chicago (house) - free parking, pool
Rental unit in Chicago
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
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- Family-friendly rentals United States
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- Bed and breakfasts South Side
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- Monthly Rentals South Side
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- Rentals with a firepit South Side
- Pet-friendly rentals South Side
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- Townhouse rentals South Side
- House rentals South Side
- Family-friendly rentals Illinois
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