Family-friendly holiday rentals in West Side
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in West 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 West Side family-friendly rentals
Family-friendly home rentals with a hot tub
Apartment in Chicago
4.97 out of 5 average rating, 94 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
23 Feb – 2 Mar
Home in Chicago
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
28 Nov – 5 Dec
Flat in Chicago
4.81 out of 5 average rating, 26 reviewsThe Professional's Playground
11–18 Nov
Apartment in Irving Park
4.78 out of 5 average rating, 46 reviewsChicago Suite 1BR/1BA (3709-G2)
31 Oct – 7 Nov
Flat in Chicago
4.63 out of 5 average rating, 8 reviewsSpacious 2bdm unit 15min to Dwtn
5–12 Jul
Loft in West Town
4.81 out of 5 average rating, 278 reviewsArtist Loft Duplex in a 1904 Former Factory
8–15 Aug
Flat in The Loop
5.0 out of 5 average rating, 3 reviewsThe Playwright's Palace
28 Oct – 4 Nov
Apartment in Chicago
4.46 out of 5 average rating, 79 reviewsCozy 2bd unit,10mins 4m dwntwn,IDEAL FOR LONG STAY
27 Sept – 4 Oct
Family- and pet-friendly home rentals
Flat in Chicago
4.84 out of 5 average rating, 480 reviewsRelaxed Bucktown/Wicker Park 1B Apt
2–9 Oct
Flat in Forest Park
4.92 out of 5 average rating, 112 reviewsVillage Cottage - Forest Park Studio Pets 72142F
10–15 May
Flat in Irving Park
4.86 out of 5 average rating, 325 reviewsThe Avondale Garden Unit
23 Feb – 2 Mar
Flat in Roscoe Village
4.96 out of 5 average rating, 238 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
2–9 Dec
Guest suite in Logan Square
4.97 out of 5 average rating, 239 reviewsStylish Studio in Historic Logan Square
21–28 Sept
Flat in Chicago
4.76 out of 5 average rating, 299 reviewsITALIAN garden apt/kids friendly/great location!!
20–27 Feb
Apartment in West Town
4.88 out of 5 average rating, 235 reviews2 King Bed Condo Easy Downtown Free Street Parking
30 Oct – 6 Nov
Flat in Chicago
4.88 out of 5 average rating, 160 reviewsBright, Gorgeous Apt Private Parking available
13–20 Jan
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 |
30 Oct – 6 Nov
Flat in Chicago
5.0 out of 5 average rating, 9 reviewsSTUNNING VIEWS, 5★AMENITY BUILDING, FREE PARKING
8–15 Jan
Guest suite in Berwyn
4.75 out of 5 average rating, 32 reviewsMusic Hot Spot’s Main Level
20–27 Jul
Guest suite in Bridgeport
4.96 out of 5 average rating, 79 reviewsSweet Home Chicago-9min downtown/pool/free parking
31 Dec – 7 Jan
Flat in Chicago
4.75 out of 5 average rating, 71 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
17–24 Nov
Flat in The Loop
4.61 out of 5 average rating, 49 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
25 Mar – 1 Apr
Place to stay in Berwyn
Beat-Town Flex Stays
8–15 Mar
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 Chicago
- Family-friendly rentals Downtown Chicago
- Family-friendly rentals Illinois
- Rentals with beach access West Side
- Rentals with a fireplace West Side
- Waterfront rentals West Side
- Loft rentals West Side
- Monthly Rentals West Side
- Rentals with lake access West Side
- Rentals with a balcony West Side
- Rentals with a hot tub West Side
- Townhouse rentals West Side
- Guest house rentals West Side
- Rentals with breakfast West Side
- Rentals with an EV charger West Side
- Rentals with a sauna West Side
- Family-friendly rentals West Side
- Rentals with a cinema West Side
- Hotel rentals West Side
- Rentals with outdoor seating West Side
- Rentals with pools West Side
- Rentals with a washing machine and dryer West Side
- Apartment rentals West Side
- House rentals West Side
- Rentals with a patio West Side
- Pet-friendly rentals West Side
- Smoking-friendly rentals West Side
- Flat rentals West Side
- Rentals with a firepit West Side
- Private suite rentals West Side
- Fitness-friendly rentals West Side
- Family-friendly rentals Cook County
- 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