Family-friendly holiday rentals in Des Plains

A spacious kitchen area is shown with modern stainless steel appliances and ample cabinet storage. A large wooden dining table is centered, set with decorative placemats. Soft light illuminates the room, complementing the neutral color scheme of the walls and cabinetry.

4.97 out of 5 average rating, 126 reviews

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

An open living and dining area features a large table set for meals, surrounded by comfortable chairs. A cozy sectional sofa sits nearby, complemented by a ceiling fan and a wall-mounted TV. Natural light flows in from windowed areas towards the rear.

4.87 out of 5 average rating, 178 reviews

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.

Superhost

A modern kitchen area features a wooden accent bar with four metal stools. Stainless steel appliances, including a refrigerator and stove, are visible. A wall clock adds a functional element to the open concept design, with neutral tones enhancing the spacious ambiance.

Apartment in Park Ridge

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

4.76 out of 5 average rating, 651 reviews

Guest suite in Riverwoods

A well-defined stone pathway leads to the entrance of the prairie-style home, bordered by lush green grass and neatly trimmed hedges. Hanging flower baskets add vibrant touches above the cozy seating area, surrounded by the serene backdrop of towering oak trees.

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.

4.95 out of 5 average rating, 509 reviews

The spacious family room features a high vaulted ceiling with exposed wooden beams. A stone fireplace provides a central focal point, and a large TV is mounted above it. Comfortable seating is arranged for relaxation, complemented by a stylish area rug.

4.97 out of 5 average rating, 134 reviews

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)♥️🎰

5.0 out of 5 average rating, 125 reviews

An open floor plan living area features a spacious couch paired with a dark coffee table. A soft area rug complements the hardwood flooring. The dining area is visible, showcasing a table for six. Large windows provide natural light to the inviting space.

Townhouse in Evanston

The NICEST place in Evanston for Families 1500Main

Fully Furnished 2-story, 2 bedroom attached Duplex with a King bed in the Primary bedroom and a pair of Twin beds in the 2nd bedroom. Couch on main floor is also a sofa bed that sleeps two if needed. Main floor is wide open floor plan. This space has been set up specifically for short-term rentals of 1-2 weeks or months and has previously been used by Guests looking for homes in the Evanston area or having construction done. We cater to Families visiting Northwestern University.

4.95 out of 5 average rating, 140 reviews

A sleek wall-mounted television is set above a modern electric fireplace, framed by a stylish metallic trim. The stone feature wall provides a textured backdrop, while warm wood flooring complements the contemporary design.

Townhouse in Des Plains

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

Apartment in Mount Prospect

One bedroom apartment near to train station

This one bedroom apartment is in downtown Mount Prospect, closed to entertainment, restaurants, coffee shop and transportation. Do you want to explorer Chicago? Metra train station is around the corner and will take you straight to Chicago! Rivers Casino in Des Plaines is 15 min drive, and Grand Victoria Casino at 40 min from apartment. If you are coming to visit friends, business or pleasure trip, this unit has everything that you need for short or long term stay.

4.93 out of 5 average rating, 107 reviews

The exterior of a two-story home is depicted, featuring a combination of white and black siding. A prominent bay window enhances the facade, while landscaped flower beds with red mulch and small plants frame the entrance. Green grass and a sidewalk lead up to the house.

4.9 out of 5 average rating, 184 reviews

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!

4.93 out of 5 average rating, 102 reviews

The exterior of a modern ranch-style home is showcased, featuring a strategic arrangement of greenery and colorful landscaping. A paved driveway leads to a welcoming entrance, flanked by two garage doors. The home is complemented by a clear blue sky and mature trees in the background.

Home in Schaumburg

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.

Home in Elk Grove Village

A bright living area is presented with a light-colored sofa and a welcoming cushion. Colorful floral artwork decorates the wall above. A round, dark wood coffee table is centered, complemented by a small planter with decorative flowers and a potted plant in the corner.

Modern Aesthetic 3bd Family Haven w/ King Bd, Yard

Unwind in this spacious, family-friendly haven in Elk Grove Village. Featuring a king bed, modern amenities, and a private yard, it’s the perfect spot for a relaxing getaway or a convenient home base to explore the area. The home is centrally located near O'hare Airport and Woodfield Mall, plus it is conveniently located near the intersection of Chicago's two major highways: I-90 and I-290, ready to take you to your destination.

4.94 out of 5 average rating, 108 reviews

4.84 out of 5 average rating, 133 reviews

A bright sleeping area features a black metal bed dressed with a yellow quilt and accented by a green decorative pillow. A light blue sofa sits nearby, complementing the space. Natural light filters through the window, partially covered by blue curtains.

Apartment in Des Plains

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

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.92 out of 5 average rating, 128 reviews

An outdoor patio is illuminated by string lights, creating a cozy ambiance. The hot tub is set against a backdrop of snowy ground, with comfortable seating arrangements nearby. The lake is visible in the background, enhancing the tranquil atmosphere.

Home in Carol Stream

Lake House Escape •Hot Tub, Bar, Fishing, Firepit

4.94 out of 5 average rating, 897 reviews

A treehouse elevated above ground showcases a wooden exterior with a balcony. An inviting staircase leads to the entrance, surrounded by lush greenery and vibrant leaves creating a natural setting. The sturdy structure is supported by wooden beams, blending harmoniously with the surrounding trees.

Treehouse in Schaumburg

Enchanted Garden Treehouse (Amenity*)

4.87 out of 5 average rating, 103 reviews

A spacious living room features a rich blue accent wall and mid-century modern furniture. Two armchairs and a plush sofa are arranged around a low coffee table. A television is mounted on the wall, complemented by decorative wall art. Natural light fills the room.

Home in Westchester

Modern 2Bdrm Westchester/Chicago Home.With Hot tub

4.91 out of 5 average rating, 146 reviews

Home in Montgomery

Skip the hotel! Relax here!

4.88 out of 5 average rating, 113 reviews

The exterior of a two-story home is displayed, featuring a spacious deck above the entrance. A well-maintained lawn surrounds the property, accented by trees and shrubbery. The driveway leads to a two-car garage, and a pathway leads towards the entrance of the house.

Home in Algonquin

On the Fox River Front/Sauna/Hot Tub/Kayaks/Grills

4.88 out of 5 average rating, 396 reviews

The exterior of a charming coach house is presented, featuring wooden shingles and a well-maintained yard. A circular table with chairs is set on the lawn, accompanied by a green umbrella for shade. Lush bushes border the property, and a wooden fence encloses the yard.

Guesthouse in Chicago

Private Coach house near Lincoln Square!

4.95 out of 5 average rating, 120 reviews

The exterior of the home features a warm brick façade, large front windows allowing natural light to fill the interior, and inviting steps leading to a decorative front door. Lush greenery and potted plants enhance the welcoming atmosphere of the entrance.

Home in Humboldt Park

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

4.83 out of 5 average rating, 104 reviews

An outdoor deck overlooks the river, featuring a circular arrangement of comfortable chairs with decorative cushions. A fire pit is situated in the center, and a covered area with a hot tub is visible in the background, surrounded by lush greenery.

Home in St. Charles

THE RIVER HOUSE Water front! Hot Tub,Sauna!

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 129 reviews

An outdoor patio area features a spacious dining table surrounded by multiple chairs, with a grill positioned nearby. A large umbrella provides shade, while string lights add ambiance. A hammock is visible in the background, and a well-maintained lawn completes the inviting setting.

Home in Streamwood

Suburban Serenity~Grill, Fire pit, Big yard~

4.78 out of 5 average rating, 160 reviews

A spacious living area features an array of seating options, including a light gray sofa and colorful accent chairs. Natural light floods in through multiple windows, highlighting the wood flooring and inviting decor. A dining table is situated nearby, along with a small coffee station.

Home in Elmhurst

Cozy Ranch w/ King Bed & 3 Baths – Great Location!

Superhost

The modern kitchen features dark cabinetry and white countertops, complemented by stainless steel appliances. A central island with seating for four is visible. Natural light enters through a nearby window, and a wall clock adds a touch of functionality. The open design connects to a dining area.

Home in Wood Dale

King bed, dog friendly, right by O'hare airport!

4.89 out of 5 average rating, 122 reviews

4.93 out of 5 average rating, 215 reviews

A modern kitchen and dining area are presented, featuring a sleek island with bar stools and a dining table with six chairs. Natural light is provided by large windows, and contemporary fixtures enhance the space's functionality and design.

Apartment in Evanston

New 3bd/1.5 bth Apt w/private prkg

4.94 out of 5 average rating, 122 reviews

A spacious living area features a large L-shaped sofa adorned with decorative cushions. A coffee table sits at the center, complemented by a cozy area rug. A brick fireplace, currently not in use, adds character, while a wall-mounted Smart TV is positioned above the mantel.

Home in Schaumburg

Pet-Friendly Sunny 3BR Near Woodfield & Downtown

4.93 out of 5 average rating, 192 reviews

A cozy living room features a pair of light-colored sofas and an accent chair, positioned around a rustic coffee table. A patterned area rug lies underfoot, while a mirror with a wooden frame and wall art enhance the space. A partial view of the kitchenette is visible in the background.

Home in Highland Park

Cozy 2-Bedroom Cottage Near Downtown Highland Park

4.97 out of 5 average rating, 224 reviews

The spacious bathroom features a freestanding tub and a glass-enclosed shower. A large mirror with a decorative frame is mounted on one wall. The floor is covered with a patterned rug, complementing the warm wall color and wood flooring.

Apartment in Evanston

Stunning, Sunny Flat with Beautiful Backyard

5.0 out of 5 average rating, 103 reviews

Apartment in Oak Park

Oak Park Space+Style Duplex Parking+Walk to Train

Family-friendly home rentals with a pool

4.96 out of 5 average rating, 147 reviews

The living area features a sectional sofa adorned with vibrant cushions beside a coffee table. Natural light filters through large windows dressed with horizontal blinds, illuminating a console with a flat-screen TV and decorative accents.

Condo in Evanston

Harmony of Evanston 1 BDR Exec Suite w/pool & Gym

Apartment in Logan Square

An aerial view of a swimming pool surrounded by a spacious wooden deck. Six comfortable loungers are positioned around the pool, with additional seating areas visible. An umbrella-covered table is set for outdoor dining, harmonizing with the greenery in the yard.

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

4.98 out of 5 average rating, 172 reviews

Apartment in Downtown Chicago

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

4.94 out of 5 average rating, 142 reviews

4.96 out of 5 average rating, 239 reviews

A red sofa is positioned in front of a brick fireplace, creating a cozy seating area. A wooden coffee table is placed in front of the sofa. Soft lighting is cast from a lamp beside the sofa, and framed photographs adorn the walls.

Guest suite in Bartlett

Cozy & Spacious Suite in Quiet Neighborhood

4.93 out of 5 average rating, 131 reviews

The modern kitchen features white cabinetry and a spacious island with four bar stools. A stainless steel refrigerator stands next to a gas stove and microwave. Natural light filters through large windows, illuminating the elegant countertops and sleek finishes.

Apartment in West Town

Cozy Duplex Down in Wicker Park East w/ Parking

Superhost

A bright living area features large windows that offer city views, enhanced by natural light. Comfortable gray seating is arranged on a patterned rug, complemented by modern decor and greenery. A flat-screen TV is mounted on the wall, alongside a stylish coffee table.

Apartment in The Loop

Spectacular 2BR Penthouse in the Loop | Roof Deck

4.81 out of 5 average rating, 359 reviews

Apartment in Downtown Chicago

A large outdoor pool is surrounded by a modern deck featuring lounge chairs. High-rise buildings provide a city backdrop against a clear blue sky.

Highrise Hideout (Fitness Center • Sauna)

4.92 out of 5 average rating, 121 reviews