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
Condo in Chicago
Urban Luxury 1BR/2BA Logan Square Condo w/Garage
Home in Chicago
Lux Urban 3BR/3BA Duplex + Parking!
Rental unit in Chicago
Spacious 2bdm unit 15min to Dwtn
Home in Miller Beach
Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
Condo in Chicago
Chicago Suite 1BR/1BA (3709-G2)
Loft in Chicago
Artist Loft Duplex in a 1904 Former Factory
Home in Miller Beach
Dunes Nat’l Park, HotTub, Sauna, Firepit, Foosball
Home in Miller Beach
Smart Home, Hot Tub, direct Beach/Nat’l Park access, luxury amenities
Family- and pet-friendly home rentals
Home in Forest Park
Charming dog friendly 2-Bath Bungalow Near Chicago
Rental unit in Chicago
Relaxed Bucktown/Wicker Park 1B Apt
Guest suite in Wood Dale
The Deer Suite
Rental unit in Chicago
ITALIAN garden apt/kids friendly/great location!!
Rental unit in Chicago
The Avondale Garden Unit
Townhouse in Hoffman Estates
a SIMPLE place
Condo in Evanston
Spacious Evanston Unit - Walk to Northwestern U
Home in Chicago
Private 3rd Floor Apartment
Family-friendly home rentals with a pool
Rental unit in Chicago
Skyline Serenity: Sauna, Hot Tub, Peloton, Views
Rental unit in Chicago
Luxury Corner 2 Bedroom in the Loop | Roof Deck
Rental unit in Chicago
The Professional's Playground
Home in Cedar Lake
Beautiful Home Oasis
Guest suite in Berwyn
Music Hot Spot’s Main Level
Guest suite in Chicago
Sweet Home Chicago-9min downtown/pool/free parking
Rental unit in Chicago
Stylish Corner 2 Bedroom in the Heart of Chicago |
Rental unit in Chicago
The Playwright's Palace
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
- Family-friendly rentals United States
- Family-friendly rentals Chicago
- Family-friendly rentals Chicago
- Family-friendly rentals Downtown Chicago
- Pet-friendly rentals South Side
- Kid-friendly rentals South Side
- Smoking-friendly rentals South Side
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- Rentals with breakfast South Side
- Condo rentals South Side
- Apartment rentals South Side
- Rentals with a hot tub South Side
- House rentals South Side
- Rentals with an EV charger South Side
- Rentals with a fireplace South Side
- Monthly Rentals South Side
- Townhouse rentals South Side
- Waterfront rentals South Side
- Rentals with pools South Side
- Rentals with a patio South Side
- Private suite rentals South Side
- Rentals with beach access South Side
- Rentals with lake access South Side
- Rentals with outdoor seating South Side
- Rentals with a fire pit South Side
- Rentals with a washer and dryer South Side
- Family-friendly rentals Illinois
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