Family-friendly vacation 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.
Vacation 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
Condo in Chicago
4.98 out of 5 average rating, 235 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Apartment in Chicago
4.87 out of 5 average rating, 159 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Home in Chicago
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
Apartment in Chicago
4.81 out of 5 average rating, 26 reviewsThe Professional's Playground
Home in Miller Beach
4.54 out of 5 average rating, 150 reviewsSecluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
Apartment in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
Condo in Chicago
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
Family- and pet-friendly home rentals
Apartment in Chicago
4.83 out of 5 average rating, 481 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Apartment in Lincoln Park
4.89 out of 5 average rating, 145 reviewsChicago Lincoln Park North Pond 2 Bedroom Pied-à-Terre
Guest suite in Wood Dale
4.9 out of 5 average rating, 431 reviewsThe Deer Suite
Apartment in Chicago
4.76 out of 5 average rating, 299 reviewsITALIAN garden apt/kids friendly/great location!!
Condo in Evanston
4.76 out of 5 average rating, 568 reviewsSpacious Evanston Unit - Walk to Northwestern U
Condo in Chicago
4.83 out of 5 average rating, 179 reviewsCan't Beat This 2min Walk to Wrigley!
Apartment in Chicago
4.92 out of 5 average rating, 397 reviewsAndersonville Living
Guest suite in Portage Park
4.95 out of 5 average rating, 120 reviewsCozy Home Living, Dogs, Kids, Free Parking, 420 OK
Family-friendly home rentals with a pool
Apartment in Chicago
4.78 out of 5 average rating, 189 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)
Apartment in Chicago
5.0 out of 5 average rating, 9 reviewsSTUNNING VIEWS, 5★AMENITY BUILDING, FREE PARKING
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
Apartment in The Loop
4.77 out of 5 average rating, 205 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Apartment in Chicago
4.62 out of 5 average rating, 50 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Place to stay in Berwyn
Beat-Town Flex Stays
Destinations to explore
- Downtown Chicago Vacation rentals
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- Lake Michigan Beach Vacation rentals
- Saugatuck Vacation rentals
- Evanston Vacation rentals
- South Haven Vacation rentals
- Naperville Vacation rentals
- South Side Vacation rentals
- South Bend Vacation rentals
- New Buffalo Vacation rentals
- Chicago Vacation rentals
- Family-friendly rentals United States
- Family-friendly rentals Chicago
- Family-friendly rentals Downtown Chicago
- Family-friendly rentals Illinois
- Rentals with an EV charger North Side
- Rentals with a hot tub North Side
- Waterfront rentals North Side
- Rentals with outdoor seating North Side
- Loft rentals North Side
- Rentals with lake access North Side
- Fitness-friendly rentals North Side
- Monthly Rentals North Side
- Rentals with a patio North Side
- Smoking-friendly rentals North Side
- Apartment rentals North Side
- Kid-friendly rentals North Side
- Rentals with a balcony North Side
- House rentals North Side
- Guesthouse rentals North Side
- Pet-friendly rentals North Side
- Bed and breakfasts North Side
- Private suite rentals North Side
- Condo rentals North Side
- Rentals with beach access North Side
- Townhouse rentals North Side
- Rentals with breakfast North Side
- Beachfront rentals North Side
- Rentals with a fireplace North Side
- Hotel rentals North Side
- Rentals with pools North Side
- Rentals with a fire pit North Side
- Rentals with a washer and dryer North Side
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- 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
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes