Family-friendly holiday rentals in Lombard

Guest suite in Glen Ellyn

A cozy living area is highlighted by a plush navy sofa adorned with a yellow accent pillow. A light-colored area rug with stripes lies beneath. The room features a decorative painting of trees and a stained glass window, adding character to the inviting space.

✽ Charming Cottage ✽ close to College/Town/Station

Charming and cozy single family home fully renovated in a superb location! This house is walking distance to the Chicago metra rail system and Wheaton College, as well as a 6 minute drive to both downtown Wheaton and downtown Glen Ellyn! Relax and unwind in this darling home that we fell in love with! The health and safety of our guests is important to us. Due to COVID-19 we are taking extra care to professionally disinfect frequently and completely between every reservation UP TO CDC STANDARDS

FamilyIndoor spacesDecor

4.93 out of 5 average rating, 216 reviews

4.89 out of 5 average rating, 222 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

Beautiful 5 bedroom, 2.5 bath home in Glen Ellyn, fully furnished with everything you may need for a wonderful stay! Located in the peaceful suburbs of Glen Ellyn, the area is perfect for families or friends who would like a comfortable getaway. Located 40 minutes from downtown Chicago and Midway airport and 30 minutes from O'Hare airport. Located nearby major highways and shopping centers. Large, private and completely enclosed backyard perfect for kids to play in or a relaxed evening of BBQ!

Indoor spacesFamilyDecor

4.85 out of 5 average rating, 184 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

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!

KitchenIndoor spacesValue

5.0 out of 5 average rating, 136 reviews

A living area showcases a wooden entertainment center with a TV, flanked by a decorative console table and two lamps. The space features hardwood floors and a neutral color palette, complemented by a circular wall mirror. A staircase in the background leads to the upper level.

Condo in Clarendon Hills

Apartment in Clarendon Hills.

Newly renovated Suite in multi family home in Clarendon Hills. Main level: fully equipped kitchen/island, dining area, living room & family room with fireplace. Upper level: Bedroom 1 - king size bed, walk in closet, private bathroom/shower. Bedroom 2 - queen bed, closet. Bedroom 3 - size bed, closet. Living room has a pull-out sofa bed. Family room with gas fireplace, access to deck/outdoor area. Easy access to restaurants, shopping (Oak Brook Mall minutes away), Metra, O’Hare.

Indoor spacesFamilyCheck-in

4.92 out of 5 average rating, 128 reviews

An upgraded patio features a hot tub illuminated in blue, with a scenic view of the lake and a vibrant sunset reflecting on the water. The outdoor dining area is nestled under string lights, adding a cozy touch to the serene atmosphere.

Home in Carol Stream

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

Visiting Chicago this holiday season? Stay somewhere that truly feels like home. We’re opening our personal lake home to guests & would love to welcome u! Tucked away in a peaceful neighborhood, it’s the perfect place to gather w/ family, relax & enjoy beautiful lake views. Spend mornings w/ coffee on the deck, afternoons fishing, grilling & evenings soaking in the hot tub or sitting by the firepit. 1-acre fenced yard to enjoy. Come settle in, make memories & enjoy our home as your own. ♡

Indoor spacesKitchenHot tub

4.78 out of 5 average rating, 157 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!

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!

FamilyKitchenBathroom

4.86 out of 5 average rating, 157 reviews

The living area features a large sectional sofa with decorative pillows, positioned opposite a television mounted on a dark wood unit. Artwork depicting colorful pixel characters adorns the wall. An archway leads to a game room with a pool table and ambient lighting.

Home in Downers Grove

Games, Grounds, Goodness in DG

Our family loves games and when travelling it is great to have entertainment for the whole family. Our game room includes a video arcade game with over 400 options, boardgames and more! Maybe simple cards or puzzles are your preference--we have them all in this fully furnished home with large backyard to play in. Bedroom 1--bunk bed with full on bottom, twin on top Bedroom 2--queen bed with room for a play pen Stay for a weekend or longer and know fun will be had!

Indoor spacesKitchenCheckout

4.93 out of 5 average rating, 164 reviews

The exterior of the vintage garage apartment is shown, featuring a bright yellow facade with two white garage doors. A large window is positioned above the doors, with greenery surrounding the property, contributing to the charming appearance.

Guesthouse in Villa Park

Eclectic Coach House Apartment

Vintage Charmer! 1935 Sears Craftsman Coach House garage apartment. Beautiful safe neighborhood surrounded by historic homes and just steps from the Illinois prairie path, parks, brewery's/bars, restaurants and more! With an eclectic boho chic vibe, featuring full kitchen and on site private washer/dryer. Overlooking an accessible lovely backyard! Close to airports and easy access to public transportation/major highways. Just 30 min from the Chicago Loop!

KitchenIndoor spacesCondition

4.82 out of 5 average rating, 186 reviews

A single-story house features a welcoming entrance with a front step and decorative wreath. Inside, cozy sleeping areas include both a queen bed and twin bunk beds. A smart TV displays a cityscape, while a dining table with six chairs is ready for meals.

Home in Lombard

Comfy Home w Access to Major Roads/Hwys, Huge Yard

Our house is perfect for a small group of friends or family looking for a clean, accessible place. It contains 3 bedrooms (2 queen beds & twin bunk beds) & 1 full bathroom, as well as a sleeper sofa with a pullout queen bed. Enjoy our smart TVs, grill or warm up by the fire pit, & even get some work or studying done! Located just minutes from major highways, parks, museums, & Yorktown Center, the journey is just getting started once you arrive!

Indoor spacesFamilyHospitality

4.92 out of 5 average rating, 123 reviews

Home in Elmhurst

Big 5BR 3.5BA Game Rm Prime Location minutes to DT

Experience ultimate luxury at our exclusive property. Nestled in a prime location, this meticulously designed retreat offers opulent furnishings, panoramic views, and bespoke amenities. Ideal for discerning travelers and work travelers seeking sophistication and comfort, indulge in a private sanctuary where every detail exceeds expectations. Discover the epitome of elegance with us and create unforgettable memories in this exquisite haven.

Indoor spacesFamilyCondition

4.93 out of 5 average rating, 100 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.

Indoor spacesKitchenBathroom

4.99 out of 5 average rating, 157 reviews

A welcoming living room is highlighted by a comfortable sectional sofa with decorative pillows. A patterned area rug covers the hardwood floor, and a reading nook features a unique egg chair. Artwork adorns the walls, complemented by greenery from potted plants.

Home in Lombard

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!

Indoor spacesKitchenCondition

Popular amenities for Lombard family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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

Indoor spacesFamilyBathroom

4.94 out of 5 average rating, 892 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*)

Indoor spacesFamilyBackyard

4.91 out of 5 average rating, 140 reviews

Home in Montgomery

Skip the hotel! Relax here!

FamilyIndoor spacesHospitality

4.83 out of 5 average rating, 102 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!

Indoor spacesKitchenNearby

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

Indoor spacesFamilyComfort

4.95 out of 5 average rating, 119 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

KitchenFamilyAccuracy

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

Game Room Suite with hot tub & Event Yurt

Indoor spacesKitchenQuiet

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

KitchenFamilyLong stay

4.95 out of 5 average rating, 506 reviews

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 120 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

KitchenFamilyCheck-in

4.99 out of 5 average rating, 107 reviews

A single-story brick home with a well-maintained front yard features green shrubs and a neat pathway leading to the entrance. Large windows allow natural light to illuminate the interior, while a tree provides shade near the entrance.

Home in Brookfield

Cozy Home in Brookfield

Indoor spacesFamilyParking

4.84 out of 5 average rating, 147 reviews

Home in Westmont

“Aunt Betty’s Cottage” sleeps up to 6 Large yard

FamilyKitchenDecor

4.92 out of 5 average rating, 566 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

FamilyIndoor spacesSleep quality

4.91 out of 5 average rating, 226 reviews

A cozy living room features a dark sectional sofa adorned with yellow accent pillows, set against a reclaimed wood wall. Large windows allow natural light to fill the space, complementing a neutral area rug that anchors the seating arrangement.

Home in Oak Park

Cozy & comfy w/free parking & W/D

FamilyKitchenPets

4.98 out of 5 average rating, 418 reviews

The living area features a comfortable sofa, paired with two woven armchairs. A rustic wooden coffee table sits at the center, adorned with a vase of fresh flowers. Natural light illuminates the space through two large windows, framed by soft curtains.

Apartment in Forest Park

Walk to Oak Park from Our Sunny Turn of the Century Apt

KitchenIndoor spacesBathroom

4.97 out of 5 average rating, 106 reviews

The kitchen features modern white cabinetry and stainless steel appliances, complemented by a spacious island with a decorative tray. Natural light floods the area through the nearby window, and a stylish backsplash adds an elegant touch to the space.

Home in Batavia

Bliss in Batavia near the Fox River

FamilyKitchenLayout

4.96 out of 5 average rating, 126 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~

KitchenIndoor spacesBackyard

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.

Just remodeled apartment close to airport and mall

FamilyIndoor spacesQuiet

4.92 out of 5 average rating, 124 reviews

4.96 out of 5 average rating, 238 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

Indoor spacesFamilyLong stay

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

Indoor spacesKitchenBarbecue

4.98 out of 5 average rating, 170 reviews

4.96 out of 5 average rating, 122 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

KitchenFamilySleep quality

Apartment in Downtown Chicago

Gold Coast Luxury: 2BR with Sweeping City Vistas

Indoor spacesFamilyPool

4.94 out of 5 average rating, 125 reviews

4.9 out of 5 average rating, 600 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

FamilyIndoor spacesCheckout

4.93 out of 5 average rating, 128 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

Indoor spacesKitchenCondition