Family-friendly holiday rentals in North Side
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in North Side
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 North Side 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 Chicago
4.85 out of 5 average rating, 293 reviewsLux Urban 3BR/3BA Duplex + Parking!
Home in Miller Beach
4.67 out of 5 average rating, 89 reviewsDunes Nat’l Park, HotTub, Sauna, Firepit, Foosball
Flat in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
Apartment in Chicago
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
Loft in Chicago
4.81 out of 5 average rating, 278 reviewsArtist Loft Duplex in a 1904 Former Factory
Home in Miller Beach
4.52 out of 5 average rating, 151 reviewsSecluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
Home in Miller Beach
4.58 out of 5 average rating, 60 reviewsRestful Refuge, Hot Tub, Firepit, Dunes Nat’l Park
Family- and pet-friendly home rentals
Flat in Chicago
4.76 out of 5 average rating, 302 reviewsITALIAN garden apt/kids friendly/great location!!
Flat in Chicago
4.83 out of 5 average rating, 483 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Apartment in Evanston
4.77 out of 5 average rating, 570 reviewsSpacious Evanston Unit - Walk to Northwestern U
Home in Chicago
4.9 out of 5 average rating, 338 reviewsPrivate 3rd Floor Apartment
Flat in Chicago
4.92 out of 5 average rating, 399 reviewsAndersonville Living
Townhouse in Hoffman Estates
4.91 out of 5 average rating, 297 reviewsa SIMPLE place
Flat in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Home in Forest Park
4.91 out of 5 average rating, 225 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
Family-friendly home rentals with a pool
Flat in Chicago
4.87 out of 5 average rating, 160 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Flat in Chicago
4.77 out of 5 average rating, 190 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
Home in Lake Forest
4.91 out of 5 average rating, 58 reviewsBeautiful 137 Year Old Farm Home (3night min)
Flat in Chicago
4.81 out of 5 average rating, 27 reviewsThe Professional's Playground
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, 205 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Flat in Chicago
4.62 out of 5 average rating, 50 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Chicago Holiday rentals
- Family-friendly rentals United States
- Family-friendly rentals Chicago
- Family-friendly rentals Downtown Chicago
- Family-friendly rentals Illinois
- Rentals with outdoor seating North Side
- Rentals with a firepit North Side
- Townhouse rentals North Side
- Rentals with an EV charger North Side
- Rentals with beach access North Side
- Loft rentals North Side
- Smoking-friendly rentals North Side
- House rentals North Side
- Flat rentals North Side
- Rentals with a hot tub North Side
- Monthly Rentals North Side
- Fitness-friendly rentals North Side
- Waterfront rentals North Side
- Rentals with lake access North Side
- Guest house rentals North Side
- Beachfront rentals North Side
- Rentals with a fireplace North Side
- Rentals with breakfast North Side
- Rentals with a balcony North Side
- Rentals with a patio North Side
- Apartment rentals North Side
- Hotel rentals North Side
- Rentals with pools North Side
- Rentals with a washing machine and dryer North Side
- Family-friendly rentals North Side
- Private suite rentals North Side
- Pet-friendly rentals North Side
- Bed and breakfasts North Side
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom