Family-friendly holiday rentals in Woodlawn, Chicago
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Woodlawn, Chicago
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Woodlawn, Chicago family-friendly rentals
Family-friendly home rentals with a hot tub
Apartment in Logan Square
4.98 out of 5 average rating, 234 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
7–14 Jan
Home in West Town
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
18–25 Nov
Flat in Chicago
4.81 out of 5 average rating, 26 reviewsThe Professional's Playground
16–23 Jan
Apartment in Irving Park
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
5–12 Apr
Loft in West Town
4.81 out of 5 average rating, 278 reviewsArtist Loft Duplex in a 1904 Former Factory
6–13 Aug
Flat in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
5–12 Jul
Apartment in Chicago
4.46 out of 5 average rating, 79 reviewsCozy 2bd unit,10mins 4m dwntwn,IDEAL FOR LONG STAY
27 Sept – 4 Oct
Family- and pet-friendly home rentals
Flat in Logan Square
4.89 out of 5 average rating, 340 reviewsSunny Logan Square Artists' home
4–11 Jan
Flat in Roscoe Village
4.96 out of 5 average rating, 238 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
2–9 Dec
Flat in Chicago
4.76 out of 5 average rating, 299 reviewsITALIAN garden apt/kids friendly/great location!!
20–27 Feb
Flat in Wicker Park
4.84 out of 5 average rating, 480 reviewsRelaxed Bucktown/Wicker Park 1B Apt
17–24 Oct
Guest suite in Wood Dale
4.9 out of 5 average rating, 430 reviewsThe Deer Suite
14–21 Nov
Flat in Irving Park
4.86 out of 5 average rating, 325 reviewsThe Avondale Garden Unit
1–8 Jul
Guest suite in Portage Park
4.95 out of 5 average rating, 120 reviewsCozy Home Living, Dogs, Kids, Free Parking, 420 OK
24 Apr – 1 May
Apartment in Evanston
4.76 out of 5 average rating, 568 reviewsSpacious Evanston Unit - Walk to Northwestern U
3–10 Dec
Family-friendly home rentals with a pool
Flat in Chicago
4.78 out of 5 average rating, 188 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
30 Oct – 6 Nov
Flat in The Loop
5.0 out of 5 average rating, 9 reviewsSTUNNING VIEWS, 5★AMENITY BUILDING, FREE PARKING
8–15 Jan
Guest suite in Berwyn
4.75 out of 5 average rating, 32 reviewsMusic Hot Spot’s Main Level
20–27 Mar
Guest suite in Bridgeport
4.96 out of 5 average rating, 79 reviewsSweet Home Chicago-9min downtown/pool/free parking
11–18 Nov
Flat in The Loop
4.76 out of 5 average rating, 204 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
17–24 Nov
Flat in Chicago
4.61 out of 5 average rating, 49 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
25 Mar – 1 Apr
Place to stay in Berwyn
Beat-Town Flex Stays
23–30 May
Quick stats about holiday rentals that are family-friendly in Woodlawn, Chicago
Total rentals
100 properties
Wifi availability
100 properties include access to wifi
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Total number of reviews
3.6K reviews
Nightly prices starting at
£32 before taxes and fees
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