Family-friendly holiday rentals in Oak Park
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Oak Park
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 Oak Park family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Chicago
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
10–17 Nov
Apartment in Chicago
4.98 out of 5 average rating, 233 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
24–31 Jan
Flat in Chicago
4.87 out of 5 average rating, 156 reviewsStunning Panoramic Chicago Views & Free Parking
20–27 Apr
Flat in Chicago
4.79 out of 5 average rating, 24 reviewsThe Professional's Playground
2–9 Jan
Flat in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
5–12 Jul
Apartment in Irving Park
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
27 Oct – 3 Nov
Loft in West Town
4.81 out of 5 average rating, 278 reviewsArtist Loft Duplex in a 1904 Former Factory
25 Jul – 1 Aug
Apartment in Chicago
4.45 out of 5 average rating, 78 reviewsCozy 2bd unit,10mins 4m dwntwn,IDEAL FOR LONG STAY
17–24 Sep
Family- and pet-friendly home rentals
Flat in Logan Square
4.89 out of 5 average rating, 339 reviewsSunny Logan Square Artists' home
1–8 Dec
Flat in Chicago
4.76 out of 5 average rating, 298 reviewsITALIAN garden apt/kids friendly/great location!!
12–19 Nov
Apartment in Evanston
4.76 out of 5 average rating, 567 reviewsSpacious Evanston Unit - Walk to Northwestern U
13–20 Feb
Guest suite in Chicago
4.95 out of 5 average rating, 120 reviewsCozy Home Living, Dogs, Kids, Free Parking, 420 OK
3–10 Oct
Flat in Chicago
4.96 out of 5 average rating, 237 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
3–10 Nov
Guest suite in Chicago
4.97 out of 5 average rating, 238 reviewsStylish Studio in Historic Logan Square
31 Aug – 7 Sep
Flat in Chicago
4.86 out of 5 average rating, 324 reviewsThe Avondale Garden Unit
31 Dec – 7 Jan
Home in Chicago
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
21–28 Mar
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 |
11–18 Sep
Flat in Chicago
5.0 out of 5 average rating, 9 reviewsSTUNNING VIEWS, 5★AMENITY BUILDING, FREE PARKING
10–17 Jun
Guest suite in Berwyn
4.74 out of 5 average rating, 31 reviewsMusic Hot Spot’s Main Level
9–16 Dec
Guest suite in Chicago
4.96 out of 5 average rating, 79 reviewsSweet Home Chicago-9min downtown/pool/free parking
15–22 Dec
Flat in Chicago
4.76 out of 5 average rating, 203 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
8–15 Feb
Flat in The Loop
4.61 out of 5 average rating, 49 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
24–31 Mar
Place to stay in Berwyn
Beat-Town Flex Stays
25 Feb – 4 Mar
Quick stats about holiday rentals that are family-friendly in Oak Park
Total rentals
140 properties
Wifi availability
140 properties include access to wifi
Rentals with dedicated workspaces
90 properties have a dedicated workspace
Pet-friendly rentals
40 properties allow pets
Total number of reviews
7.4K reviews
Nightly prices starting at
$54 SGD before taxes and fees
Destinations to explore
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