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
Apartment in Chicago
4.97 out of 5 average rating, 29 reviewsThe Playwright's Palace
Home in Chicago
4.85 out of 5 average rating, 309 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
Apartment in Chicago
4.75 out of 5 average rating, 48 reviewsThe Professional's Playground
Condo in Chicago
4.98 out of 5 average rating, 261 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Apartment in Chicago
4.56 out of 5 average rating, 16 reviewsSpacious 2bdm unit 15min to Dwtn
Family- and pet-friendly home rentals
Apartment in Chicago
4.9 out of 5 average rating, 382 reviewsSunny Logan Square Artists' home
Apartment in Chicago
4.87 out of 5 average rating, 179 reviewsChicago Lincoln Park North Pond 2 Bedroom Pied-à-Terre
Guest suite in Chicago
4.95 out of 5 average rating, 150 reviewsCozy Home Living, Dogs, Kids, Free Parking, 420 OK
Townhouse in Chicago
4.85 out of 5 average rating, 162 reviewsDowntown Elegance ✨ Private Yard Parking
Apartment in Chicago
4.93 out of 5 average rating, 423 reviewsAndersonville Living
Apartment in Chicago
4.95 out of 5 average rating, 488 reviews2nd floor of 1908 brick two-flat in Logan Square
Apartment in Chicago
4.94 out of 5 average rating, 215 reviewsStylish Chicago Apartment near Public Transit
Apartment in Palos Hills
4.94 out of 5 average rating, 166 reviewsAunt Linda's Apartment with a View in Palos
Family-friendly home rentals with a pool
Apartment in Chicago
4.77 out of 5 average rating, 207 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
Apartment in Chicago
4.77 out of 5 average rating, 228 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 Downtown Chicago
- Rentals with a washer and dryer South Side
- Waterfront rentals South Side
- Bed and breakfasts South Side
- Private suite rentals South Side
- Condo rentals South Side
- Rentals with outdoor seating South Side
- Rentals with lake access South Side
- Rentals with an EV charger South Side
- Rentals with a patio South Side
- Rentals with beach access South Side
- Rentals with a fireplace South Side
- Apartment rentals South Side
- Pet-friendly rentals South Side
- Rentals with a hot tub South Side
- House rentals South Side
- Fitness-friendly rentals South Side
- Rentals with breakfast South Side
- Smoking-friendly rentals South Side
- Townhouse rentals South Side
- Kid-friendly rentals South Side
- Monthly Rentals South Side
- Rentals with pools South Side
- Rentals with a fire pit South Side
- Family-friendly rentals Illinois
- Family-friendly rentals Cook County
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