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, 225 reviewsWhiting Getaway
Nov 13 – 20
Home in Berwyn
4.92 out of 5 average rating, 240 reviewsPrivate apartment with retro vibe
Aug 28 – Sep 4
Home in Chicago
4.97 out of 5 average rating, 318 reviewsCozy garden apartment historic Jackson Bvld.
Nov 3 – 8
Home in Chicago
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
Feb 27 – Mar 6
Home in Lake View
4.98 out of 5 average rating, 206 reviewsWrigleyville Southport Studio
Nov 25 – Dec 2
Home in Chicago
4.97 out of 5 average rating, 356 reviewsGreystone Haven in Logan Square
Sep 1 – 6
Home in Chicago
4.95 out of 5 average rating, 171 reviewsParadise on the Park
Oct 16 – 23
Home in Forest Park
4.91 out of 5 average rating, 223 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
Jun 25 – Jul 2
Kid-friendly apartment rentals
Apartment in Pilsen Historic District
4.89 out of 5 average rating, 202 reviewsSpectacular Pilsen Studio for 2!
Feb 3 – 10
Apartment in Chicago
4.89 out of 5 average rating, 243 reviewsModern
Oct 20 – 27
Apartment in Chicago
4.98 out of 5 average rating, 130 reviewsModern Apt with style & comfort in Pilsen Chicago
Jul 21 – 28
Apartment in Chicago
4.91 out of 5 average rating, 169 reviewsHandicap accessible apartment w/Level-2 EV Charger
Dec 3 – 10
Apartment in Chicago
4.84 out of 5 average rating, 175 reviewsThe Cottage
Sep 25 – Oct 2
Apartment in Chicago
4.85 out of 5 average rating, 234 reviewsTeeny Tiny Bohemian Lodge - Clean & Affordable
Oct 14 – 21
Apartment in Chicago
4.89 out of 5 average rating, 300 reviewsVintage Bridgeport Apartment
Jul 7 – 14
Apartment in Chicago
4.85 out of 5 average rating, 258 reviewsCharming loft style suite
Sep 11 – 18
Kid-friendly condo rentals
Condo in Chicago
4.86 out of 5 average rating, 126 reviewsMcCormick 2B/2Ba for up to 6 guests w Opt Parking
Jan 15 – 22
Condo in Chicago
4.87 out of 5 average rating, 107 reviewsSpacious Duplex in Great Location
Sep 19 – 26
Condo in Bronzeville
4.87 out of 5 average rating, 135 reviewsThe En Bronze ~ 7mins To Dining & Downtown Chicago
Sep 27 – Oct 4
Condo in Lincoln Square
4.98 out of 5 average rating, 329 reviewsLincoln Square Gem!
Oct 17 – 24
Condo in Chicago
4.93 out of 5 average rating, 187 reviewsPvt 1bdr Rogers Park, Loyola, Northwestern.
Oct 23 – 30
Condo in Chicago
4.86 out of 5 average rating, 123 reviews3D Tour! Designer Condo near Logan Square
Nov 28 – Dec 5
Condo in Oak Park
4.88 out of 5 average rating, 164 reviewsAttractive Flat - Historic Oak Park
Feb 23 – Mar 2
Condo in East Garfield Park
4.9 out of 5 average rating, 136 reviewsEast Garfield Park 2 Bedroom
Oct 29 – Nov 5
Destinations to explore
- Downtown Chicago Vacation rentals
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