
Family-friendly holiday rentals in Cook County
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Cook County
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.
Indoor spacesKitchenHeating

New sauna, steps from beach and National Park
Perfect for family or friends to relax and enjoy Indiana’s Dunes National Park! The Holliday House is a 2022 custom built home with lake views and a beach path just STEPS from the front door! This 2000 sq ft open concept design features 3 bedrooms and 3 bathrooms, 16’ ceilings, open great room with beautiful indoor/outdoor kitchen, custom dining seating for 8, and loft hammock. Hosts live next door and are easily available if needed! Everything is on the 1st floor except for the 3rd bedroom.
Indoor spacesKitchenAccess

Rockin' 2Bed steps to shops/food/train
This musically-inspired vintage 2 BR is perfectly placed in Oak Park and we know you'll have a rockin' vacation here. Steps to shops, cafes, train, and FL Wright home. With a cassette wall, reading nook, and many other cute touches. The apartment is a vintage brownstone with charming details, like original woodwork. Street parking available. Easy access to Chicago.The place is an older Chicago brownstone, with a lived-in feel. NO PARTIES!! Upstairs neighbors can be heard walking and moving
KitchenFamilyWalkability

The Ashlin House.
Stay at our family-friendly home on a quiet, cobblestone street on vacation or business. We've recently repainted the exterior and painted the master BR. Walking distance to quaint Downtown Whiting , Lake Michigan, Whihala Beach & Lakefront trails. The Horseshoe Casino, Wolf Lake & Pavilion, Hammond Sportsplex, Calumet College, PNW, IUN, U of Chicago, BP, & golf courses are a short drive. See Chicago's Skyline at Lakefront Park. Chicago's attractions & Hard Rock Casino are < 30 mins away.
Indoor spacesKitchenBathroom

Dog Friendly Cozy North Naperville 3 BED/2 BA Home
Welcome to the Naperville Nest! Rare North Naperville opportunity to find a home suited for the whole family! Pets are more than welcome to enjoy the 1/2 acre fully fenced in yard. This is a a fully updated home minutes from Downtown Naperville, I-88 and many more exciting destinations in the Western Suburbs. You will feel at home whether you're inside or outside...each bedroom has it's own TV and the outdoor living includes natural gas firepit & grill/dining table...this home has it all!
KitchenFamilyHeating

Chicago Home (1st floor) by Midway near Downtown
Hello, Welcome in 1st floor apt, where 3 rooms are available with newly remodelled kitchen, bathroom and livingroom. LOCATION, convenient location, walking distance to grocery store and few restaurants near by, also walking distance to public transportation bus 62 and 62 H. 5 min driving to Midway airport and 15 min driving to downtown Chicago. Easy access to public transportation to get to Chicago downtown. In addition to convenient location, apt offers access to yard and free parking
KitchenIndoor spacesGetting around

Charming, Sunny Apartment with Backyard Garden
House of the Blue Doors Enjoy staying with us in this spacious 1st floor flat. Furnished by the resident designer in tasteful neutrals, original curated artwork, one of a kind furniture and accent pieces. Sip morning coffee or a glass of wine in the sunlit kitchen or front porch, fire up the backyard grill for a barbecue. Soak in the award winning Chicago ceramic artist designed and made floor in the bathroom. Close to Northwestern, Chicago, Lake Michigan, everything Evanston offers.
Indoor spacesKitchenAir conditioning

Cozy Ranch w/ King Bed & 3 Baths – Great Location!
Feel at home at this cozy split-level ranch with separate spaces perfect for relaxing—whether you’re staying with family or traveling for work. Watch your favorite show in the basement while someone else is peacefully reading a book on the main level or taking a nap upstairs. Located on a quiet, dead-end street, but just 22 mins from O’Hare Airport, minutes from I-290 and 83rd, and 10 minutes from Oak Brook Mall. Our excellent guest-to-bathroom ratio ensures comfort for everyone!
FamilyKitchenAmenities

Comfortable and Cozy Apartment
Enjoy this simple and cozy apartment! Located just a few blocks from stores like Walgreens, Aldi, Target, Laundromat and various restaurants. Its conveniently located just a 10 minute walk from the orange line cta train station. Disfrutá de la sencillez de este alojamiento tranquilo y céntrico. Ubicada a dos minutos de tiendas como target, Walgreens, Aldi, Lavandería y restaurantes . Estamos a 10 minutos del aeropuerto midway y 15 minutos del centro de Chicago.
KitchenFamilyParking

Cozy Schaumburg 5 br/3.5ba w/ bonus rooms/office
Luxurious–Cozy Ranch Stunning 5-bedroom, 3.5-bath home offers spacious modern living on a quiet cul-de-sac. The home features a gourmet kitchen with a Viking 48” stove and Omega cabinets, a master suite with a coffee bar, his-and-hers bathrooms, and a jacuzzi tub. Enjoy two fireplaces, three wet bars, and a basement with a pool table, arcade games, an 85” TV, and a kids' playroom. Outside, the backyard has a patio, gazebo, and firepit.
KitchenFamilyTV

Modern Boho house in Lombard 7 min to Metra
Kick back and relax in this calm, stylish space. Visiting family in Chicagoland area? Traveling for work? Lombard is centrally located 30 min to everywhere! The house is only 6 min to Oakbrook Shopping and Business Center and upscale shopping and fabulous restaurants like RH with rooftop restaurant, 8 min to Yorktown Shopping Center. Whatever your travel purpose is, we will be happy to host you! Welcome home!
FamilyIndoor spacesDecor

3BD Home Mins from Airport | Free Wi-Fi + Parking
Cozy home near O'Hare airport with a huge park just behind the backyard, located in one of the safest neighborhoods in the City of Chicago. Quick access to the expressway and short walk to the CTA Blue Line train/bus station. Conveniently located within 5 miles of: - O'Hare Airport - Rosemont/Donald E. Stephens Convention Center - All-State Arena - Fashion Outlets of Chicago
KitchenFamilyNearby
Popular amenities for Cook County family-friendly rentals
Family-friendly home rentals with a hot tub

Modern Getaway w/ Hot Tub, Lrg Yard, Parking
FamilyIndoor spacesParking

Lake Home Retreat-HotTub• FirePit• Kayak• Fishing!
Indoor spacesFamilyBackyard

Enchanted Garden Treehouse (Amenity*)
Indoor spacesFamilyValue

Private hot tub - King bed suite - Free parking
FamilyKitchenSolo travel

H&H 1896 - Spacious, Fully Stocked, & Free Parking
Indoor spacesKitchenQuiet

Modern 2Bdrm Westchester/Chicago Home.With Hot tub
FamilyIndoor spacesLocation

Beachfront- Lake Michigan-Hot Tub-Heated Pool
Indoor spacesKitchenCondition

Game Room Suite with hot tub & Event Yurt
KitchenIndoor spacesLocation
Family- and pet-friendly home rentals

Cozy Home in Brookfield
FamilyIndoor spacesSleep quality

Picturesque Apartment in Berwyn
KitchenFamilyNearby

Cozy & comfy w/free parking & W/D
KitchenFamilyBiking

Like a Treehouse!
Indoor spacesFamilyHospitality

Vintage Suite Home Chicago by Sox/Park/Transit
KitchenFamilyBathroom

Beautiful Chicago Greystone
KitchenFamilyWi-Fi

Gorgeous 5 BR Gem Sleeps 18 with Tons of Games!
Indoor spacesFamilyComfort

Luxury SOHO Styled Two-Level Townhouse - Old Town
Indoor spacesFamilyAmenities
Family-friendly home rentals with a pool

Comfy 3BR 2BA, Liv+Fam Rm, Prime, 3-Car Parking
FamilyIndoor spacesDecor

Fun & cozy getaway w/POOL/game room/FREE parking
KitchenFamilyLayout

Bayless Dune Lodge at West Beach - Indiana Dunes!
Indoor spacesKitchenBackyard

Just remodeled apartment close to airport and mall
Indoor spacesFamilyLocation

Professional's Playground (Fitness Center • Sauna)
KitchenFamilyBathroom

Farm Themed Guesthouse!
Indoor spacesFamilyParking

Gold Coast Luxury: 2BR with Sweeping City Vistas
KitchenIndoor spacesCheckout

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
KitchenIndoor spacesAir conditioning
Destinations to explore
- Pet-friendly rentals Cook County
- RV rentals Cook County
- Waterfront rentals Cook County
- Rentals with an accessible height toilet Cook County
- Townhouse rentals Cook County
- Private suite rentals Cook County
- Rentals with a sauna Cook County
- Apartment rentals Cook County
- Loft rentals Cook County
- Rentals with pools Cook County
- Boutique hotels Cook County
- Serviced apartment rentals Cook County
- Rentals with beach access Cook County
- Hotel rooms Cook County
- House rentals Cook County
- Luxury rentals Cook County
- Condo rentals Cook County
- Rentals with an accessible height bed Cook County
- Rentals with breakfast Cook County
- Rentals with a kayak Cook County
- Rentals with lake access Cook County
- Bed and breakfasts Cook County
- Beachfront rentals Cook County
- Guesthouse rentals Cook County
- Rentals with a hot tub Cook County
- Family-friendly rentals Illinois
- Family-friendly rentals United States
- Wrigley Field
- Soldier Field
- Lincoln Park
- United Center
- Grant Park
- Navy Pier
- Millennium Park
- Indiana Dunes State Park
- Naval Station Great Lakes
- 875 North Michigan Avenue
- Six Flags Great America
- University of Chicago
- The Field Museum
- Shedd Aquarium
- Humboldt Park
- Loyola University Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Union Park
- Beachwalk Vacation Rentals
- Frank Lloyd Wright Home and Studio
- Donald E Stephens Convention Center
- Byline Bank Aragon Ballroom
- Washington Park Zoo
- Things to do Cook County
- Landmarks Cook County
- Museums Cook County
- Outdoors Cook County
- Cultural tours Cook County
- Architecture Cook County
- Food tours Cook County
- Art workshops Cook County
- Things to do Illinois
- Museums Illinois
- Food tours Illinois
- Art workshops Illinois
- Landmarks Illinois
- Cultural tours Illinois
- Outdoors Illinois
- Architecture Illinois
- Things to do United States
- Shopping and fashion United States
- Cultural tours United States
- Dining United States
- Museums United States
- Architecture United States
- Workouts United States
- Art workshops United States
- Flying United States
- Wellness United States
- Food tours United States
- Wildlife United States
- Landmarks United States
- Water sports United States
- Performances United States
- Tastings United States
- Galleries United States
- Cooking United States
- Beauty United States
- Outdoors United States





