Family-friendly holiday rentals in Schaumburg

The open living area features a modern dining table set for four, complemented by a spacious kitchen visible in the background. A comfortable seating area is arranged with plush couches and decorative pillows, illuminated by natural light from large windows.

4.98 out of 5 average rating, 187 reviews

Modern Spacious Quiet Home Near O'Hare -Deck&Yard

Experience a modern and quiet retreat in our big 4 Bedroom 2.5 Bathroom home. Perfect blend of comfort and convenience. Sleeps 9 people. Master Suite. Bedrooms: 3 King and Two Full Beds. 6 Smart TVs. Open floor plan with fully equipped kitchen where you can cook and create experiences with family. Big Fenced Back yard with a Big Deck. Parking 3 cars. Close to restaurants, shopping, trails, and parks. 6 miles to Schaumburg Convention Center, 17 miles to O'Hare Airport, 5 miles to Woodfield Mall

4.94 out of 5 average rating, 174 reviews

A bright living area features a comfortable sofa arranged around a modern coffee table. A work desk is positioned near the window, with natural light spilling in. Artwork adorns the walls, and greenery adds a touch of life to the space, enhancing the welcoming atmosphere.

Apartment in West Dundee

Charming Riverfront Stay | Heart of Downtown

Welcome to The Riverfronts! Three boutique hotel rooms perfectly situated along the river in downtown West Dundee, offering scenic views and modern comforts. ✔ Riverfront Location: Enjoy the scenic riverwalk just steps away. ✔ Prime Downtown Spot: In the heart of downtown Dundee, minutes from top attractions and dining. ✔ Exclusive Group Booking: Reserve just one or all three units for your entire party. ✔ Outdoor Firepit: Unwind by the firepit, perfect for evening gatherings. ✔ Sleeps 4: Each

4.99 out of 5 average rating, 111 reviews

A bright living area features a cozy sofa and an armchair, arranged around a small desk workspace. Sliding glass doors open to an outdoor patio area, allowing natural light to fill the room. Soft curtains frame the doors, enhancing the inviting atmosphere.

Apartment in Elgin

Peaceful Elgin APT King Bed

Located in a sleepy suburban neighborhood, this freshly renovated apartment offers everything for a weekend getaway, business trip, or extended stay with a full kitchen, open living space & bedroom. Enjoy peace & nature while still being minutes away from restaurants, shopping, outdoor activities & all the Chicago suburbs have to offer. The Tipi BNB is a walkout lower-level basement APT that provides guests with the privacy and accessibility of a separate entrance and self check in/check out

4.94 out of 5 average rating, 883 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*)

Summer's here, the treehouse air conditioned and cozy, and the hot/cool 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!

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.

4.95 out of 5 average rating, 492 reviews

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.

A spacious living area features a cozy gray sofa adorned with colorful cushions, complemented by two vibrant blue chairs. A wooden coffee table rests on a floral area rug, while a flat-screen TV is mounted on the wall above a modern fireplace. Natural light enters through large windows.

4.97 out of 5 average rating, 120 reviews

Modern & Clean 3 Bedroom Ranch House with Sunroom

Kick back and relax in this fully renovated and stylish space. House is stocked with new kitchenware, appliances, smart TVs. This rental has everything you need! 6 miles to Schaumburg Convention Center, 17 miles to O'Hare Airport, 5 miles to Woodfield Mall. Enjoy restaurants, parks, golf courses, Legoland, Medieval Times and much more. This is a 3 bedroom 1 bathroom house with a beautiful sunroom that sleeps up to 6 people (2 in each bedroom). Garage is not available for guests' use.

5.0 out of 5 average rating, 206 reviews

A serene living area features a large sliding glass door leading to a deck with unobstructed views of Round Lake. Natural wood accents adorn the wall, while a plush sofa and a small coffee table create a relaxing seating space.

Home in Round Lake Beach

Round Lake Getaway Retreat

Looking for a calming, peaceful lakeside getaway for you and your loved one? Come stay at our remodeled retreat with private waterfront access to Round Lake. Enjoy peace and reflection meditating on the spirited lake waters rolling into shore. Wake up to inspirational lake views with soul warming coffee, tea or cocoa. Savor deep or lazy conversation with your loved one, surrounded by dreamy décor and captivating nature. Come and relax, restore, and rejuvenate by the lake!

Townhouse in Hoffman Estates

A cozy living area features a black leather sofa paired with decorative pillows. A glass coffee table sits atop a patterned rug, complemented by a lamp and a small plant. The staircase leads to an upper level, with a wall map artwork enhancing the space.

4.89 out of 5 average rating, 388 reviews

a SIMPLE place

Booking the entire house with 100% privacy. It has 2 driveway parking spaces and street parking. Garage may be available. CHECK-IN and OUT are flexible. I set checkout at 11am (text me if you need late checkout). The space is perfect for a family of 4. It is located about 20 minutes from O'Hare airport and 40 minutes from Chicago downtown. Infants and pets are welcome (please text me for over size pets or more than 2 pets) Play pan is available upon request.

5.0 out of 5 average rating, 134 reviews

A charming cottage is framed by lush greenery and colorful flower planters. The white exterior features multiple windows, allowing ample natural light. A welcoming front porch leads to the entrance, adorned with patriotic bunting, inviting guests to enjoy the serene surroundings.

Cottage in Barrington

Cozy French Inspired Cottage in rural setting

Relax and escape to our charming, one of a kind cottage. Beautifully decorated with period furniture and tastefully updated with modern amenities. The cottage offers slate tile and hardwood floors. Original pine floors line the upstairs loft bedrooms. Cook in a French inspired country kitchen with butcher block counter tops. Rural setting, yet minutes away from everything! Downtown is a 20 min. walk and the Metra will take you to the city in 45 minutes!

A bright living area features large windows draped with yellow curtains, allowing natural light to fill the space. A tan leather sofa and two blue chairs are arranged around a round coffee table, with a light area rug underfoot and decorative wall art adding a modern touch.

4.88 out of 5 average rating, 112 reviews

Near Chicago&O’Hare|Fenced yard+Game room|king bed

Family-friendly vacation rental with modern amenities! ★ Can sleep 5 people ★ 3 Bedrooms, 4 beds ★ Rest peacefully in a king-size bed ★ Watch your favorite shows on a 65" 4K TV ★ Stay connected with fast Wi-Fi. ★ Convenient private driveway. Visit Waterworks Park (4 mins) Woodfield Mall (10 mins) Medieval Times (12 mins) Legoland (14 mins) Schaumburg Convention Center (15 mins) Numerous dining options nearby. Book today and create lasting memories!

4.97 out of 5 average rating, 526 reviews

Loft in West Dundee

124 Lofts #2 - Downtown Dundee - Walk to Dining

124 Lofts is a boutique collection of modern, design-forward lofts set within a beautifully restored historic building in downtown West Dundee. This listing is for Loft #2, a one-bedroom space featuring exposed brick, timber ceilings, and clean finishes that feel both character-driven and easy to enjoy. Each loft includes a king bed, private bath, kitchenette, fast Wi-Fi, and a 60" smart TV, just steps from restaurants, shops, and the Fox River.

A stylish living room features a comfortable gray sofa adorned with colorful cushions. A round coffee table sits in front, complemented by a unique wooden chair and playful orange poufs. Large windows allow natural light, while a decorative mural of angel wings graces the dark feature wall.

4.87 out of 5 average rating, 135 reviews

InstaWorthy! Modern Gem, Perfect Family Getaway-Pe

Have fun with the whole family at this stylish place! - Minutes away from Woodfield Mall, Legoland Waterworks Indoor Water Park, Golf, Outdoors, and more! - Private Driveway - Blazing Fast 1GB internet speed - 60 4K Smart TV w/ Roku Live TV - Pack n Play, High Chair, Stroller - Stocked Kitchen with Coffee and Waffle Bar! - Outdoor Patio Area w/ games - Working Desk Area. - Firepit, Corn Hole, Pool Table - King Size Bed in Main

Popular amenities for Schaumburg family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.92 out of 5 average rating, 128 reviews

Home in Carol Stream

Lake Home Retreat! HotTub• FirePit• Kayak• Fishing

4.87 out of 5 average rating, 133 reviews

A spacious outdoor deck is covered with a bright shade sail, providing relief from the sun. Comfortable wicker chairs with soft cushions create a cozy seating area, overlooking the peaceful river and surrounding greenery.

Home in Algonquin

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

4.91 out of 5 average rating, 130 reviews

Home in Montgomery

Skip the hotel! Relax here!

4.92 out of 5 average rating, 288 reviews

Home in McHenry

River House with Deck and Hot Tub

4.95 out of 5 average rating, 274 reviews

Home in Woodstock

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

4.84 out of 5 average rating, 401 reviews

A winding red mulch pathway leads towards a charming A-frame house nestled among tall trees. The surrounding lawn is lush and green, with a peaceful natural setting enhanced by the canopy of leaves above.

Chalet in Ingleside

"A" Frame Brandenburg Lake

4.88 out of 5 average rating, 388 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!

4.96 out of 5 average rating, 104 reviews

A large, inviting above-ground pool features clear blue water, with a pink flamingo float resting on the surface. Surrounding trees provide natural shade, while a gazebo with soft lighting is visible in the background, offering a cozy and relaxing ambiance.

Guest suite in Flossmoor

Fun game-room suite with hot tub & optional Yurt

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 127 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.

Home in Des Plains

NEW~2 Spa Baths~Game Room~Prime Area~Big Yard~

4.91 out of 5 average rating, 559 reviews

A modern kitchen showcases dark wood cabinetry and stainless steel appliances, including a refrigerator and gas stove. A granite countertop extends into a bar area with three metal stools. A microwave and kettle are placed on the counter, illuminated by overhead lighting.

Guest suite in Wood Dale

The Deer Suite

4.89 out of 5 average rating, 115 reviews

A living area is presented with a comfortable gray sofa adorned with decorative pillows. Two white chairs with blue accents are positioned nearby. Natural light enters through a large window, complemented by dark blue curtains. A patterned rug enhances the inviting ambiance.

Home in Wood Dale

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

4.89 out of 5 average rating, 156 reviews

The exterior of a charming historic home features dark blue siding and a welcoming front porch with three steps leading up to the entrance. Large windows on either side of the door allow for natural light, while lush greenery surrounds the property, enhancing its curb appeal.

Home in Elgin

Charming Elgin Home with a Great Location

4.89 out of 5 average rating, 215 reviews

A cozy living room features a brick fireplace as a focal point, surrounded by comfortable leather seating arranged for relaxation. Light-colored curtains frame large windows, while a plush area rug adds warmth to the wooden floor. A wooden door and wall decor complement the inviting space.

Home in Glen Ellyn

Home in Glen Ellyn

4.77 out of 5 average rating, 150 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!

4.85 out of 5 average rating, 179 reviews

The exterior of a single-story home is framed by lush green grass and dark mulch landscaping. A welcoming pathway leads to the front door, adorned with a seasonal wreath. A large tree provides shade, and a white fence marks the boundary of the yard.

Home in Naperville

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

4.84 out of 5 average rating, 104 reviews

Home in Des Plains

Cozy Home near O'Hare & fun Hubs

Family-friendly home rentals with a pool

Condo in Elk Grove Village

The living area features a comfortable gray sofa facing a modern TV stand. A light rug lies beneath a white coffee table adorned with a small plant. Natural light filters through a large window, complemented by soft curtains. A desk and chair are positioned in the corner.

4.92 out of 5 average rating, 118 reviews

Just remodeled apartment close to airport and mall

Guest suite in St. Charles

A spacious bedroom features a queen bed dressed in crisp white linens, accompanied by decorative pillows. Soft lighting is provided by a bedside lamp, while an accent rug adds warmth to the wood floor. A built-in shelf displays various decorative items.

5.0 out of 5 average rating, 321 reviews

Peaceful Private Coach-House in St. Charles

4.96 out of 5 average rating, 236 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

4.9 out of 5 average rating, 596 reviews

A cozy bedroom features a spacious bed dressed in bold black and white striped bedding. A decorative red pillow adds a pop of color. A framed artwork of a rabbit is displayed above the bed, complemented by bedside tables with a lamp and a small potted plant.

Apartment in Uptown

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

4.96 out of 5 average rating, 119 reviews

An open-concept living space is showcased, featuring modern kitchen appliances, a dining table with seating for six, and a comfortable sofa. Large windows allow natural light to fill the area, providing views of the outdoor landscape.

Condo in Evanston

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

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.

4.98 out of 5 average rating, 163 reviews

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

4.88 out of 5 average rating, 134 reviews

A spacious living area features floor-to-ceiling windows that showcase panoramic views of the Chicago skyline. Modern furnishings include a comfortable sectional sofa and an elegant coffee table. A dining area is visible in the background, complemented by sleek decor and ample natural light.

Apartment in West Town

Top of River West: Luxe Penthouse for Groups