Family-friendly vacation rentals in Naperville

4.87 out of 5 average rating, 710 reviews

A spacious living area is highlighted by a black sofa facing a light-colored coffee table. A vibrant area rug adds color underfoot. The walls are adorned with colorful vinyl records and framed artwork, while original woodwork details frame the open layout leading to the dining area.

Apartment in Oak Park

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

Guest suite in Saint 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 out of 5 average rating, 303 reviews

Peaceful Private Coach-House in St. Charles

Enjoy our cozy and peaceful Coach-house , private entrance with everything you need for a wonderful stay. Newly renovated and updated throughout. Queen bed with mattress topper, studio area includes Smart TV, water station, Keurig coffee machine and quick-set lock. Even though you are less than a mile from downtown St. Charles and 4 miles to the Geneva train station you have a private area. You may see deer out your window overlooking the pool and tennis. Not suitable for children or pets.

4.87 out of 5 average rating, 150 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!

4.87 out of 5 average rating, 157 reviews

A single-story ranch home is presented with a dark blue exterior and white shutters. A neatly trimmed lawn and concrete pathway lead to the front door. Flanking the entrance, small shrubs add greenery, while a tall evergreen tree stands nearby.

Home in Montgomery

Nice, Private Ranch Home

Nice private ranch home in a quiet neighborhood. Fox River and the river bike trail are only 3 minutes away, Rush Copley Medical Center, lots of shopping and dining options within minutes, Phillips park zoo, and water park very close, major roadways to Chicago. 10 min, from downtown Aurora where you can find the Hollywood Casino, Paramount theatre, many shopping stores and you can enjoy a walk along the Fox river, Fox valley mall and the Chicago premium outlets mall are only 20min away.

4.95 out of 5 average rating, 131 reviews

A bedroom features hand-painted floral murals on the walls, complemented by light-colored curtains framing a window. A spacious bed with white linens is centered on a patterned floor. A cozy sitting area with a dark wicker chair adds to the comfort of the space.

Home in Geneva

The Secret Garden

Summer is COOLER in Geneva! Located just 3 blocks from shops and restaurants in beautiful, downtown Geneva. Our space can sleep up to 4 comfortably. We offer amazing amenities like plush bed & linens, array of coffee and teas and goodies, 50" flat screen smart tv for watching movies after a day of fun in Geneva. Beautiful bath equipped with everything, including homemade salt scrub. A secure, separate entrance to come & go. It is a basement soace so ceilings are lower than average home.

4.98 out of 5 average rating, 183 reviews

A living room features a mid-century velvet sofa in a rich green hue, paired with a tan leather chair. Natural light streams through large windows, illuminating a glass coffee table and a decorative wall with layered wooden frames. The original brick fireplace adds character to the space.

Home in Berwyn

Retro Modern Bungalow | free parking | fire pit

Experience the city in style at Retro Modern Bungalow, the perfect pad for up to 4 friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

4.99 out of 5 average rating, 209 reviews

A spacious living area features a corner sectional sofa with soft cushioning and a cozy throw. Large windows provide natural light and city views. A simple coffee table sits in front, with light-colored carpet underfoot, enhancing the comfortable atmosphere.

Apartment in Aurora

Penthouse In The Historic Hobbs

Experience luxury and historic charm at the Penthouse in the Historic Hobbs. Built in 1892, and restored in 2023, this new one bedroom corner unit offers a panoramic view of the Aurora skyline. Cook a delicious meal in the fully stocked kitchen. Dine at the bespoke table in the window bay under the iconic onion dome. Relax on the cozy sofa and enjoy a movie on the big screen TV. Rest in the plush king-sized bed. This urban retreat is near coffee, shopping, art and entertainment.

4.89 out of 5 average rating, 152 reviews

A cozy living space features a vibrant red sofa and wooden dining chairs surrounding a circular table. Natural light fills the room through large windows adorned with white curtains, highlighting a woven area rug and potted plants near the window.

Home in West Chicago

The Train Conductor's Cottage

Enjoy your stay at the Train Conductor’s Cottage! Welcome to our charming home in a family neighborhood, just a couple of blocks away from the Metra train to Chicago & from West Chicago's authentic Mexican restaurants. We are close to Wheaton College, North Central College, Dupage Airport, and Central Dupage Hospital. Rest and relax in a queen bed, full bed, two twin beds, two full bathrooms, spacious children's play area. Amazon Fire stick, WiFi, TV. “All aboard!”

4.91 out of 5 average rating, 122 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!

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, 360 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.

4.92 out of 5 average rating, 309 reviews

The exterior of the Coach House features white siding and a covered entry, framed by greenery. Two doors are visible, leading into the house, while a decorative wall piece is positioned above the entrance. A pathway lined with plants guides the way to the front steps.

Guesthouse in Batavia

Quaint Batavia Coach House

The Coach House is located behind our house. It is a private and separate little house. It is located close to the river path and lots of restaurants. The upstairs is one big room that has 1 queen and 2 twin beds. The upstairs also has a full bath. The TV in main living area on first floor is not hooked up to cable, but you can log into all of your apps and have access to news via YouTube TV, Netflix, Prime etc.

4.99 out of 5 average rating, 127 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!

Popular amenities for Naperville family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guesthouse in Lincoln Square

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.

4.89 out of 5 average rating, 341 reviews

Private Coach house near Lincoln Square!

4.95 out of 5 average rating, 157 reviews

An outdoor space is showcased featuring a hot tub under a pergola with string lights, providing a relaxed ambiance. Comfortable seating is arranged around a firepit table, complemented by a gas grill visible in the background.

Home in Bridgeport

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

4.96 out of 5 average rating, 280 reviews

A modern kitchen features a large stainless steel island with seating for three. Black cabinetry offers ample storage space, complemented by open shelves displaying various kitchen items. Pendant lights hang above, illuminating a stylish workspace adorned with greenery, while industrial elements add character.

Loft in Wicker Park

Tea Studio in Wicker Park Spring Factory

Apartment in East Rogers Park

An open-concept living and dining area is showcased with a gray sectional sofa and a wooden coffee table. A modern ceiling fan hangs above, and natural light fills the space. A dining table with six chairs is positioned nearby, adjacent to a sleek kitchen.

4.85 out of 5 average rating, 101 reviews

Spacious Beautiful Condo

4.96 out of 5 average rating, 165 reviews

An outdoor patio is showcased, featuring a rectangular fire table surrounded by four cushioned chairs. The wooden decking contrasts with the subdued colors of the furniture. A partial cover is draped over one corner, providing shade from the sun.

Condo in West Town

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

4.81 out of 5 average rating, 168 reviews

A spacious living area features large windows that allow natural light to brighten the room. Comfortable seating arrangements, including a sectional sofa and armchairs, surround a central coffee table. A stone fireplace serves as a focal point, with a television mounted above it.

Home in Saint Charles

California Ranch on Acre Lot - Hot Tub & Sauna

4.97 out of 5 average rating, 149 reviews

The game room features a red-themed layout filled with arcade machines, a pool table, and foosball. A variety of classic games are showcased, providing a fun atmosphere for guests. Bright lighting illuminates the room, inviting enjoyable gaming experiences.

Apartment in Dunning

Belmont Pleasures - hot tub / arcade gaming room

Apartment in Humboldt Park

An open and spacious living area features a white sectional sofa and unique cow print coffee table. The dining space is equipped with round chairs, and a modern kitchen is visible in the background. Light streams through frosted glass block windows, enhancing the airy atmosphere.

4.86 out of 5 average rating, 492 reviews

Checkerboard Studio, Private Outdoor Hot Tub, Yard

Family- and pet-friendly home rentals

4.79 out of 5 average rating, 156 reviews

A light-filled living area is presented with a soft blue couch and a glass coffee table atop a textured rug. A comfortable armchair complements the seating arrangement. French doors lead to an outdoor deck, enhancing the connection with nature.

Townhouse in Yorkville

Riverfront Townhome in Downtown Yorkville

4.91 out of 5 average rating, 200 reviews

A cozy seating area is highlighted by a modern electric fireplace beneath a mounted television displaying streaming options. Soft cushions and a pastel throw blanket add comfort to the light-colored chair. A touch of decor is presented with wall art and a small side table.

Apartment in Oak Park

Lovely, spacious 2bd, 1bath home w/free parking

Guest suite in Portage Park

The living area features a comfortable sofa adorned with colorful cushions, positioned beside a unique wooden coffee table. A striking piece of wall art adds visual interest, while a dining area with modern chairs is visible in the background, complemented by potted plants.

4.94 out of 5 average rating, 456 reviews

Peaceful Portage Park Apartment

Apartment in Little Village

A modern kitchen is equipped with sleek white cabinetry and a stainless steel stove and microwave. Natural light illuminates the space through a window, while a stylish backsplash adds visual interest. A coffee maker, kettle, and other essentials are arranged on the countertop, showcasing functionality.

4.86 out of 5 average rating, 186 reviews

Cozy Beauty Sleeps 5 - 10 Min to Downtown PacMan

4.92 out of 5 average rating, 185 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

Guest suite in Portage Park

A brick bungalow features a welcoming front porch adorned with a US flag. The porch includes a railing and seating area, while flower pots add greenery. Stairs lead up to the front door, which is detailed with a decorative screen.

4.95 out of 5 average rating, 179 reviews

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK

4.92 out of 5 average rating, 143 reviews

A spacious artist loft features a living area with hardwood floors and large windows allowing natural light. A leather sofa is positioned in the center, with stylish chairs nearby. The open kitchen is visible in the background, along with a modern dining space under soft lighting.

Loft in Brookfield

1920s fully updated unique open artist loft space

4.91 out of 5 average rating, 146 reviews

A single-story ranch-style home is depicted, featuring a brick and siding facade. A two-car garage is positioned on the right side, with a well-maintained lawn and neat landscaping in the front yard. Clear skies and scattered clouds provide an inviting backdrop.

Home in Bolingbrook

The Sunshine Spot

Family-friendly home rentals with a pool

4.95 out of 5 average rating, 122 reviews

A bright living area features large windows that offer city views. Comfortable seating arrangements include a pair of teal sofas and a wooden armchair. A coffee table sits at the center on a soft area rug, accompanied by a flat-screen TV mounted on a nearby wall.

Condo in Evanston

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

4.89 out of 5 average rating, 112 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 River West

Top of River West: Luxe Penthouse for Groups

5 out of 5 average rating, 11 reviews

The living area features a modern couch adorned with yellow and white pillows, accompanied by two accent chairs. A dining table with blue chairs is set on a cozy area rug. Natural light enters through sliding glass doors, leading to a small balcony.

Apartment in Warrenville

Luxury 2BR - Pool, Pickleball, Gym, Sauna & More!

4.9 out of 5 average rating, 563 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

4.9 out of 5 average rating, 115 reviews

An outdoor pool is surrounded by lounge chairs in various colors, creating a bright and inviting atmosphere. Tall buildings are visible in the background, and the pool reflects the clear blue sky overhead.

Apartment in South Loop

The Executive's Escape (2BD / 2BA)

5 out of 5 average rating, 10 reviews

Home in Elmhurst

Elmhurst 4BR Home with Pool | Mid-Term Ready

4.9 out of 5 average rating, 122 reviews

A spacious bedroom features large floor-to-ceiling windows, allowing natural light to fill the room. A large bed with neutral bedding is complemented by a contemporary desk and chair setup, which is arranged near a wood-framed lamp. A subtle area rug lies beneath the bed.

Apartment in River North

50th Floor Mag Mile Studio