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

Newly remodeled O’hare oasis
Your family will be close to everything when you stay at this centrally-located place. This 3 bed 2 bath newly remodeled private home will have everything you need to feel comfortable during your stay! You are 3 miles from O’Hare airport ,2 miles from Rivers Casino, 1 mile from Allstate Arena, and 4 miles from Fashion outlet mall of Chicago. Enjoy spacious living room and Rec Room, large eat-in kitchen with all new appliances! King bed . 2 queen Beds and pullout sofa with queen bed for sleeping

Entire house, close to O'Hare airport
You and your family will be close to all amenities when you stay at this centrally-located place. 5 miles from O'hare Airport, 1.3 miles from Allstate Arena, 4 miles from Rosemont Convention Center and 5 miles from Fashion Outlet of Chicago. Few mins from Rivers Casino, Shopping Centers, Restaurants, Express way. Easy access to I-90 & I-294. 15 miles away from Chicago Downtown. A newly renovated space with extremely fast WIFI up to 800mbps, suitable for WFH. Walking distance to a close by lake.

Modern Garden apartment (WHOLE UNIT)
Freshly Remodeled , Lower Level garden apartment one bedroom one bath. Older building with wooden floors. If hearing people upstairs walking can bother you , do NOT book it please .Very Spacious with its open concept layout. Parking is right next to the main entrance of the building. 24/7 perimeter monitoring cameras. The Condo is very close to the Metra Train. It is !5 min away from O'Hare airport and 10min to outlets Absolutely NO parties, NO gathering Quiet hours 10 pm till 6.00 am

Master qtr close to nature & easy urban facilities
This amazing prairie style home sits on 2 acre land surrounded by lush lawn and majestic oak trees - a nature lover's dream with unparalleled serenity. Vacation-like setting blends country-like quiet with nearby conveniences including shopping, trains, restaurants, highways, Ravinia (18 MINs drive). 5 MINs to I 294. 20 MINS to O'HARE; 5 Mins to Discover, Baxter; 10 MINs to Walgreens Deerfield campus, TRINITY INT'L UNIVERSITY; 15 MINS to Lake Forest Academy. 25 MINs to Great Lakes Navy Base.

Enchanted Garden Treehouse (Amenity*)
Summer's here, the treehouse air conditioned and cozy, and the hot tub ready! Relax in our luxurious, 420 friendly, very private, 4' deep cedar hot tub nestled in the evergreens, while the moon and stars swirl overhead, the waterfall tumbles into the koi pond, and the fire table and torches blaze. The stream makes this a wildlife refuge, with many birds, squirrels, rabbit & fox. Come experience the magic and make a special memory! See why Chgo Magazine rates us top 3 staycations in Chgo!

NEW~2 Spa Baths~Game Room~Prime Area~Big Yard~
✅Updated Home- RARE 1/3+ Acre Fenced Yard 🏠 ✅Huge Vaulted Ceiling Family Room 🛋️ ✅2 Full Updated Bathrooms on Main Level🪥🛀 ✅Game Room w/Air Hockey & Basketball🏒🏀 ✅Dining Room Seats 10🪑 🍽️ ✅Quiet Neighborhood + Convenient Location🏘️ ✅Open Kitchen Floorplan 🍳👨🍳 ✅Outdoor Seating🌳 ✅EZ Driveway Parking for 4 Cars🚗🏎️ ✅Close to O’Hare Airport(8 Min)🛫 ✅Close to Stephens Convention Center(12 Min)👨👩👧👧 ✅Close to Allstate Arena(7 Min)🎤 ✅Close to River’s Casino(8 Min)♥️🎰

Upscale 3 bed 1.5 bath near Chicago O'Hare Airport
Free! coffee station with 12 types of Keurig pods such as Dunkin/Starbucks/McDonalds/Green tea/Decaf etc. Make your favorite coffee on our commercial brewer. Newly remodeled, luxurious, 3 bedrooms, 1.5 bathrooms duplex house located 10 minutes from O’Hare International Airport. 10-15 minutes from Allstate Arena, Rosemont Convention Center, Fashion Outlets of Chicago and Rivers Casino. Downtown Chicago is ~25 minutes away with an easy access to I-94 and I-294 Expressways.

3bedrooms& 2 bath (king bed) in newly updated Home
Located in the West suburbs of Chicago you'll be far away from the chaos of the city, yet close to the highway to visit downtown whenever you like. You'll have a great night sleep in either the king, queen, or full size beds. All with brand new mattress and linens. Get ready for a night out in 1 of our 2 full size bathrooms. Enjoy a large backyard for kids to play and if you decide to have a family BBQ. Whether you're coming here for work or play we have you covered.

Stunning, Sunny Flat with Beautiful Backyard
Home away from home in a wonderful and walkable Evanston neighborhood, convenient to downtown, Lake Michigan, Northwestern and more. Treat yourself and your family to this wonderful two-bedroom, masterfully remodeled flat, with all the conveniences and comfort. Off street private parking. Recent updates: New king size bed, 65-inch HD TV, washer & dryer, and more. We follow EPA/CDC protocol and prepare for your stay with intensive cleaning and disinfecting.

Designer's Dream in the North Shore!
Welcome to the newly designed cottage at Longmeadow. A tranquil escape from the city hustle of Downtown Chicago. Enjoy the serene setting while close proximity to town amenities, public transit and beautiful trails and parks. A cozy retreat in the wintertime to snuggle up with a great book and hot cocoa. It's also a perfect summer cottage for adventurers looking to take advantage of the beautiful landscape ! Check us out on: Instagram! longmeadowcottage

Cozy Home by O'Hare + EV Plug
Family-friendly 3BR/2BA home in Des Plaines! Enjoy arcade games, board games, and an EV charger. Nestled in a quiet neighborhood near parks, shopping, and entertainment. Just minutes from Des Plaines Theatre, Rivers Casino, Mystic Waters, and Fashion Outlets of Chicago. Ideal for families or groups seeking comfort, fun, and convenience with easy access to top attractions and O'Hare Airport. Your perfect home base for exploring the Chicago area!

Safe, Great Location 2 Bedroom Apt, Self Check-In
This gorgeous second-floor apartment is located only 10 minutes from O'Hare International Airport. Located near Des Plaines River Road and Toughy Ave., you will be close to not only the airport but 7 minutes to Rivers Casino, 10 minutes from the Rosemont Entertainment District, and 30 minutes from downtown Chicago. The apartment is minutes away from two major highway interstates, which makes this a commuters ideal location.
Popular amenities for Des Plains family-friendly rentals
Family-friendly home rentals with a hot tub

The River House Sauna/Kayaks/Hot Tub/Fire Pit

Private Coach house near Lincoln Square!

Ukrainian Village 3BR/3BA • Private Patio, Parking

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

The Tailor House: 2BR w/ Hot Tub near Woodstock Sq

The Spa of Downtown Whiting

Belmont Pleasures - hot tub / arcade gaming room

Skip the hotel! Relax here!
Family- and pet-friendly home rentals

Luxury New Home O’Hare WiFi Yard EV Charger

Cozy 2-Bedroom Cottage Near Downtown Highland Park

Peaceful Portage Park Apartment

Luxe Limewash Getaway w/Sun Deck

2-Car Garage Access | Cal King Bed | Fenced Yard

Victorian House in Heart of Rogers Park

Suburban Serenity~Grill, Fire pit, Big yard~

Cozy 2 bedroom house/w garage in Skokie
Family-friendly home rentals with a pool

The Metropolitan Retreat (Fitness Center • Sauna)

Spectacular 2BR Penthouse in the Loop | Roof Deck

5-Star Gold Coast Experience in a Luxe 2BR Retreat

Whole Flat in Private Club. Walk to L, Dining & Shows

Paradise with Pool & Games

Hot tub. Heated Pool. In town location.

Peaceful Private Coach-House in St. Charles

Harmony of Evanston 1 BDR Exec Suite w/pool & Gym
When is the best time to visit Des Plains?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £138 | £135 | £149 | £142 | £162 | £169 | £176 | £164 | £158 | £158 | £159 | £153 |
| Avg. temp | -4°C | -2°C | 4°C | 10°C | 16°C | 21°C | 24°C | 23°C | 19°C | 12°C | 5°C | -1°C |
Quick stats about holiday rentals that are family-friendly in Des Plains

Total holiday rentals
Explore 80 holiday rentals in Des Plains

Nightly prices starting at
Des Plains holiday rentals start at £37 per night before taxes and fees

Verified guest reviews
Over 3,350 verified reviews to help you choose

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
80 of Des Plains holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Des Plains rentals

4.6 Average rating
Des Plains stays receive an average rating of 4.6 out of 5 from guests
Destinations to explore
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- Family-friendly rentals Cook County
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- Family-friendly rentals United States
- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Grant Park
- Navy Pier
- Soldier Field
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- The Field Museum
- Guaranteed Rate Field
- Union Park
- Lincoln Park Zoo
- Wilmot Mountain Ski Resort
- Chicago River Walk
- Frank Lloyd Wright Home and Studio
- Garfield Park Conservatory
- Oak Street Beach
- Museum of Science and Industry
- Illinois Beach State Park
- Willis Tower
- Naval Station Great Lakes





