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
4.98 out of 5 average rating, 234 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Mar 18 – 25
Home in Chicago
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
Nov 14 – 21
Apartment in Chicago
4.81 out of 5 average rating, 26 reviewsThe Professional's Playground
Nov 17 – 24
Condo in Chicago
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
Mar 21 – 28
Home in Miller Beach
4.54 out of 5 average rating, 150 reviewsSecluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
Apr 23 – 30
Apartment in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
Jul 5 – 12
Loft in Chicago
4.81 out of 5 average rating, 278 reviewsArtist Loft Duplex in a 1904 Former Factory
Aug 4 – 11
Apartment in Chicago
5.0 out of 5 average rating, 3 reviewsThe Playwright's Palace
Dec 23 – 30
Family- and pet-friendly home rentals
Apartment in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Feb 10 – 17
Apartment in Chicago
4.89 out of 5 average rating, 339 reviewsSunny Logan Square Artists' home
Feb 18 – 25
Apartment in Irving Park
4.86 out of 5 average rating, 324 reviewsThe Avondale Garden Unit
Jan 12 – 19
Apartment in Chicago
4.9 out of 5 average rating, 154 reviewsSpacious unique artist's home in Pilsen
Sep 13 – 20
Apartment in Chicago
4.76 out of 5 average rating, 299 reviewsITALIAN garden apt/kids friendly/great location!!
Feb 16 – 23
Apartment in Chicago
4.84 out of 5 average rating, 480 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Sep 12 – 19
Home in Forest Park
4.91 out of 5 average rating, 223 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
Jun 23 – 30
Condo in Evanston
4.76 out of 5 average rating, 568 reviewsSpacious Evanston Unit - Walk to Northwestern U
Dec 2 – 9
Family-friendly home rentals with a pool
Apartment in Chicago
4.76 out of 5 average rating, 203 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Dec 14 – 21
Apartment in Chicago
5.0 out of 5 average rating, 8 reviewsSTUNNING VIEWS, 5★AMENITY BUILDING, FREE PARKING
Apr 12 – 19
Home in Cedar Lake
4.85 out of 5 average rating, 72 reviewsBeautiful Home Oasis
Mar 3 – 10
Guest suite in Berwyn
4.74 out of 5 average rating, 31 reviewsMusic Hot Spot’s Main Level
Aug 8 – 15
Guest suite in Bridgeport
4.96 out of 5 average rating, 79 reviewsSweet Home Chicago-9min downtown/pool/free parking
Dec 18 – 25
Apartment in The Loop
4.78 out of 5 average rating, 188 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
Nov 26 – Dec 3
Apartment in Chicago
4.61 out of 5 average rating, 49 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Mar 11 – 18
Place to stay in Berwyn
Beat-Town Flex Stays
Mar 4 – 11
Destinations to explore
- Downtown Chicago Vacation rentals
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