Family-friendly vacation rentals in Highland Park
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Highland Park
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 Highland Park family-friendly rentals
Family-friendly home rentals with a hot tub
Condo in Chicago
4.98 out of 5 average rating, 233 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Jan. 24 – 31
Home in Richmond
4.93 out of 5 average rating, 143 reviews"About Time" You will love it! -12 beds
Feb. 8 – 15
Home in Chicago
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
Nov. 10 – 17
Home in Bristol
4.82 out of 5 average rating, 85 reviewsBeautiful Lakehouse sleeps 12 Boat/Pets/HotTub/Ski
Feb. 11 – 18
Home in McHenry
4.93 out of 5 average rating, 217 reviewsRiver House with Deck and Hot Tub
Jul. 2 – 9
Condo in Chicago
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
Oct. 27 – Nov. 3
Home in Lake Villa
4.87 out of 5 average rating, 38 reviewsLakeside Getaway
Jul. 24 – 31
Apartment in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
Jul. 5 – 12
Family- and pet-friendly home rentals
Condo in Evanston
4.76 out of 5 average rating, 566 reviewsSpacious Evanston Unit - Walk to Northwestern U
Feb. 13 – 20
Apartment in Wilmette
4.89 out of 5 average rating, 235 reviewsSpacious Garden Apartment with Sauna and Fireplace
Jul. 15 – 22
Apartment in Chicago
4.76 out of 5 average rating, 298 reviewsITALIAN garden apt/kids friendly/great location!!
Dec. 11 – 18
Apartment in Chicago
4.96 out of 5 average rating, 237 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Nov. 3 – 10
Home in Chicago
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
Dec. 1 – 8
Apartment in Forest Park
4.92 out of 5 average rating, 112 reviewsVillage Cottage - Forest Park Studio Pets 72142F
May 9 – 16
Apartment in Chicago
4.89 out of 5 average rating, 339 reviewsSunny Logan Square Artists' home
Dec. 1 – 8
Home in Forest Park
4.91 out of 5 average rating, 223 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
Jun. 25 – Jul. 2
Family-friendly home rentals with a pool
Chalet in Ingleside
4.84 out of 5 average rating, 369 reviews"A" Frame Brandenburg Lake
Oct. 23 – 30
Apartment in Chicago
4.78 out of 5 average rating, 188 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
Sep. 11 – 18
Apartment in Chicago
4.87 out of 5 average rating, 156 reviewsStunning Panoramic Chicago Views & Free Parking
Apr. 20 – 27
Home in Lake Forest
4.91 out of 5 average rating, 58 reviewsBeautiful 137 Year Old Farm Home (3night min)
Mar. 1 – 8
Apartment in Chicago
4.79 out of 5 average rating, 24 reviewsThe Professional's Playground
Jan. 2 – 9
Apartment in Chicago
5.0 out of 5 average rating, 9 reviewsSTUNNING VIEWS, 5★AMENITY BUILDING, FREE PARKING
Feb. 12 – 19
Guest suite in Chicago
4.96 out of 5 average rating, 79 reviewsSweet Home Chicago-9min downtown/pool/free parking
Dec. 15 – 22
Guest suite in Berwyn
4.74 out of 5 average rating, 31 reviewsMusic Hot Spot’s Main Level
Dec. 9 – 16
Quick stats about vacation rentals that are family-friendly in Highland Park
Total rentals
20 properties
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Total number of reviews
670 reviews
Nightly prices starting at
$123 CAD before taxes and fees
Destinations to explore
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