Kid-friendly vacation rentals in South Side
Find and book unique kid-friendly rentals on Airbnb
Top-rated kid-friendly rentals in South Side
Guests agree: these kid-friendly rentals 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 kid-friendly rentals
Kid-friendly house rentals
Home in Whiting
4.8 out of 5 average rating, 227 reviewsWhiting Getaway
Home in Uptown
4.9 out of 5 average rating, 336 reviewsPrivate 3rd Floor Apartment
Home in West Loop
4.97 out of 5 average rating, 318 reviewsCozy garden apartment historic Jackson Bvld.
Home in Berwyn
4.91 out of 5 average rating, 248 reviewsPrivate apartment with retro vibe
Home in Porter
4.83 out of 5 average rating, 155 reviewsModern Indiana Beach Home Near Lake Michigan
Home in Chicago
4.97 out of 5 average rating, 358 reviewsGreystone Haven in Logan Square
Home in Roscoe Village
4.94 out of 5 average rating, 213 reviewsModern Home RoscoeVillage/Wrigley Free St Parking
Home in West Town
4.95 out of 5 average rating, 173 reviewsParadise on the Park
Family-friendly apartment rentals
Apartment in Bridgeport
4.89 out of 5 average rating, 301 reviewsVintage Bridgeport Apartment
Apartment in Chicago
4.89 out of 5 average rating, 245 reviewsModern
Apartment in Pilsen Historic District
4.85 out of 5 average rating, 237 reviewsTeeny Tiny Bohemian Lodge - Clean & Affordable
Apartment in Chicago
4.84 out of 5 average rating, 176 reviewsThe Cottage
Apartment in Cicero
4.98 out of 5 average rating, 204 reviewsCOZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
Apartment in Little Italy
4.98 out of 5 average rating, 199 reviewsSpacious 2BR on Quiet St - Free Park/Late Checkout
Apartment in Blue Island
4.93 out of 5 average rating, 266 reviewsCharming Unique 2 Bdrm Apartment in Victorian Home
Apartment in Forest Park
4.98 out of 5 average rating, 288 reviewsWalk to Oak Park from Our Sunny Turn of the Century Apt
Family-friendly condo rentals
Condo in Chicago
4.92 out of 5 average rating, 100 reviewsModern designed 2bed/2bath | Heart of Bronzeville!
Condo in Lincoln Square
4.97 out of 5 average rating, 333 reviewsLincoln Square Gem!
Condo in Bronzeville
4.87 out of 5 average rating, 136 reviewsThe En Bronze ~ 7mins To Dining & Downtown Chicago
Condo in West Town
4.97 out of 5 average rating, 708 reviewsGreat location. Free parking.
Condo in Humboldt Park
4.97 out of 5 average rating, 103 reviewsStylish 3BR + Free Parking 10-15mins from Downtown
Condo in Chicago
4.87 out of 5 average rating, 126 reviews3D Tour! Designer Condo near Logan Square
Condo in Chicago
4.86 out of 5 average rating, 127 reviewsMcCormick 2B/2Ba for up to 6 guests w Opt Parking
Condo in Chicago
4.82 out of 5 average rating, 125 reviews-CHICAGO STUDIO IN JEFFERSON PARK O'HARE ROSEMONT-
Destinations to explore
- Downtown Chicago Vacation rentals
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