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 Chicago
4.98 out of 5 average rating, 237 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Home in West Town
4.85 out of 5 average rating, 293 reviewsLux Urban 3BR/3BA Duplex + Parking!
Flat in Chicago
4.87 out of 5 average rating, 165 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Flat in Chicago
4.83 out of 5 average rating, 29 reviewsThe Professional's Playground
Apartment in Irving Park
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
Loft in West Town
4.81 out of 5 average rating, 278 reviewsArtist Loft Duplex in a 1904 Former Factory
Flat in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
Flat in The Loop
5.0 out of 5 average rating, 8 reviewsThe Playwright's Palace
Family- and pet-friendly home rentals
Flat in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Flat in Logan Square
4.83 out of 5 average rating, 485 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Flat in Chicago
4.76 out of 5 average rating, 302 reviewsITALIAN garden apt/kids friendly/great location!!
Guest suite in Logan Square
4.97 out of 5 average rating, 242 reviewsStylish Studio in Historic Logan Square
Guest suite in Wood Dale
4.9 out of 5 average rating, 437 reviewsThe Deer Suite
Flat in Irving Park
4.86 out of 5 average rating, 329 reviewsThe Avondale Garden Unit
Flat in Chicago
4.87 out of 5 average rating, 164 reviewsBright, Gorgeous Apt Private Parking available
Home in Forest Park
4.9 out of 5 average rating, 227 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
Family-friendly home rentals with a pool
Flat in Chicago
4.77 out of 5 average rating, 207 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Guest suite in Berwyn
4.75 out of 5 average rating, 32 reviewsMusic Hot Spot’s Main Level
Guest suite in Bridgeport
4.96 out of 5 average rating, 79 reviewsSweet Home Chicago-9min downtown/pool/free parking
Flat in Chicago
4.77 out of 5 average rating, 191 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
Flat in The Loop
4.6 out of 5 average rating, 52 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Place to stay in Berwyn
Beat-Town Flex Stays
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
£31 before taxes and fees
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