Family-friendly holiday rentals in Wheaton

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.

4.93 out of 5 average rating, 216 reviews

✽ 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

FamilyKitchenLaundry

4.92 out of 5 average rating, 128 reviews

Home in Carol Stream

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

Come enjoy our beautiful home it's the perfect place to relax, unwind & enjoy peaceful lake views. Whether you’re fishing, soaking in the hot tub or sipping coffee on the deck, it’s a quiet home away from home on a serene cul-de-sac. Enjoy stunning views of the lake while grilling or relaxing by the firepit on the beautifully landscaped patio & in the hot tub 🥂 🐶 Up to 2 furry babies are welcome & they’ll love the almost 1-acre fenced yard! 🌅 See weekly & monthly discounts for longer stays

Indoor spacesFamilyTV

4.82 out of 5 average rating, 119 reviews

An open living room features hardwood floors and a comfortable seating area with grey armchairs. A dining area is visible in the background, adorned with a table set for dining. Natural light streams in through large windows dressed with curtains.

Home in Glen Ellyn

Book Now & Build Great Memories in Cozy Cape Cod!

Fall in love w/ this beautiful 3 level Cape Cod home! This amazing 4 bedrooms, 2 bath home offers a modern kitchen w/ stainless steel appliances& granite countertops w/ pantry stocked w/ amenities. Open living room/dining room combo offers natural sunlight and beautiful french doors that lead into a cozy 3 season porch room with lots of windows. The main level has 2 bedrooms, full bath, & hardwood floors. The 2nd level has 2 bedrooms, full bath & lower level has rec room w/ games for family fun!

FamilyKitchenHeating

5.0 out of 5 average rating, 117 reviews

A bright and open kitchen and dining area features a large island with seating and a dining table set for multiple guests. Modern appliances are visible in the background, along with stylish cabinetry. Natural light fills the space through large windows with sheer curtains.

Home in Geneva

Outdoor Oasis • Fire Pit • EV Charger • Near Town

Private office, high speed internet. EV Charger. Spacious,King Bed.Great outdoor space, fire pit, Indoor fireplace. Close to towns. Great weekend getaway. Great rate. Close to two beautiful parks, huge soccer field, water splash park, slide and swing and etc. Mins away from to the fox river trail. Less than 2 miles away from beautiful downtown Geneva, historic shopping district with over 160 specialty shops and restaurants. Less than 3 miles away from another beautiful downtown of St. Charles.

Indoor spacesKitchenGetting around

4.89 out of 5 average rating, 220 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

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!

FamilyKitchenComfort

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!

Indoor spacesKitchenNearby

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

Beautifully renovated house with and open floor plan, gourmet fully stocked kitchen, 4 bedrooms, 2.5 bathrooms and smart tv's in all the bedrooms and quick reliable wifi for all to enjoy. Home has large lot with amazing deck and 4 season room that also doubles as a separate work space as well as a smaller second workspace as . House also has a fully finished basement with 2 of the bedrooms, a full bathroom and a large theater room with a sectional sleeper sofa if more space is needed.

Indoor spacesFamilyCleanliness

4.91 out of 5 average rating, 185 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!”

FamilyKitchenBack garden

4.92 out of 5 average rating, 106 reviews

Home in Carol Stream

Family Haven Retreat, Sleep 16 Plus guests

"Welcome to our 6-bedroom retreat for 16 guests, a haven featuring an expansive deck with outdoor furniture and a fire pit. Inside, a vast living room with a pool table and fireplace awaits. Enjoy numerous TVs, a chef's dream kitchen, and a luxurious master bathroom with a walk-in shower. With laundry, study space, two living and dining rooms, and a garage, this safe, spacious home is nestled near a children's playground for added family fun."

KitchenFamilyParking

4.94 out of 5 average rating, 137 reviews

The living area features a comfortable seating arrangement with a sofa and two armchairs. A round coffee table sits in the center on a patterned area rug. Soft lighting enhances the neutral wall tones, while a decorative plant adds a touch of greenery.

Flat in Warrenville

“The remote retreat”

We have a cozy one bedroom apartment that is available on the top floor of the home and has its own independent and separate entrance! Comes with free parking on premises; recently renovated; neighborhood is safe and quiet. Shopping center with grocery store, laundry mat and restaurant is available within walking distance! We are only 5 minutes from the expressway I-88 and 10 minutes from Naperville and the outlet mall in Aurora!

KitchenFamilyLong stay

4.99 out of 5 average rating, 156 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!

FamilyIndoor spacesGetting around

4.87 out of 5 average rating, 138 reviews

A spacious living area features two comfortable leather sofas and a wooden coffee table. A dining area with a small table and four chairs is visible, along with a bookshelf displaying various items. Soft lighting and neutral walls contribute to an inviting ambiance.

Guest suite in Wheaton

Guest Suite by Wheaton College

Come and enjoy visiting your Wheaton College student while staying a short walk from campus. Our apartment has two bedrooms, a well-equipped kitchenette, laundry, bathroom, and living room. The apartment is in the basement our family home with a private entrance and both bedrooms have large windows with lots of natural light. This apartment is not equipped or suitable for children.

Indoor spacesKitchenAccuracy

Popular amenities for Wheaton family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.91 out of 5 average rating, 138 reviews

Home in Montgomery

Skip the hotel! Relax here!

KitchenFamilyTV

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!

FamilyKitchenView

4.94 out of 5 average rating, 891 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*)

KitchenIndoor spacesAir conditioning

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

KitchenFamilyAccuracy

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 spacesFamilyHospitality

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, 506 reviews

Master qtr close to nature & easy urban facilities

KitchenIndoor spacesLocation

4.96 out of 5 average rating, 182 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 Getaway w/ Hot Tub, Lrg Yard, Parking

KitchenIndoor spacesParks

4.89 out of 5 average rating, 104 reviews

A spacious kitchen featuring a large island with seating for several guests. Dark cabinetry contrasts with the light granite countertops. Exposed wooden beams and rustic brick walls add character to the open layout. Modern appliances are present, enhancing the functional design.

Home in West Side

United Center Compound w/Rooftop, Hot Tub, Sauna

Indoor spacesFamilyLocation

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 106 reviews

A spacious living area features a large sectional sofa adorned with throw pillows and a soft blanket. A flat-screen TV is mounted on the wall opposite, and natural light streams in through multiple windows, creating a bright, comfortable space.

Home in Geneva

Spacious 4BR Modern Home—Walk to Downtown Geneva!

FamilyKitchenSleep quality

4.87 out of 5 average rating, 182 reviews

A living area features a brown leather sofa accompanied by two accent chairs, all arranged around a glass-top coffee table. Natural light enters through a large window adorned with flowing curtains, complemented by a decorative mirror and wall-mounted storage.

Home in Lisle

Cozy House, Main Road Access, Close to Colleges

FamilyKitchenWifi

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

KitchenFamilySleep quality

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!

KitchenFamilyBack garden

Guest suite in St. Charles

4.84 out of 5 average rating, 190 reviews

Cozy, Comfy, Close to Downtown

KitchenIndoor spacesHospitality

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~

KitchenFamilyGetting around

4.9 out of 5 average rating, 194 reviews

Home in Aurora

Large Luxury Home: King Beds, Theater & BBQ

KitchenIndoor spacesQuiet

4.96 out of 5 average rating, 178 reviews

Home in Huntley

The Main Event Game House on the Huntley Square!

FamilyKitchenValue

Family-friendly home rentals with a pool

Apartment 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, 123 reviews

Just remodeled apartment close to airport and mall

FamilyKitchenAccuracy

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 spacesKitchenBack garden

4.98 out of 5 average rating, 169 reviews

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.

Flat in Logan Square

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

KitchenIndoor spacesCondition

4.94 out of 5 average rating, 125 reviews

Flat in Downtown Chicago

Gold Coast Luxury: 2BR with Sweeping City Vistas

KitchenIndoor spacesCheck-in

4.96 out of 5 average rating, 146 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.

Apartment in Evanston

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

KitchenIndoor spacesComfort

4.81 out of 5 average rating, 354 reviews

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.

Flat in Chicago Loop

Spectacular 2BR Penthouse in the Loop | Roof Deck

FamilyIndoor spacesTV

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.

Flat in West Town

Cozy Duplex Down in Wicker Park East w/ Parking

FamilyIndoor spacesLayout