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Family-friendly vacation rentals in Homewood

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Homewood

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

An outdoor seating area features a cushioned sectional sofa and a wooden coffee table, overlooking a heated in-ground pool. Lounge chairs are positioned nearby, surrounded by trees, with a view of Lake Michigan in the background.

Guest suite in Gary

4.98 out of 5 average rating, 107 reviews

Beachfront- Lake Michigan-Hot Tub-Heated Pool

Lake Michigan - Beachfront w/Heated In-Ground Pool- Hot Tub - Indiana Dunes National Park - Private Basement Guest Suite - 2 Bedroom/2 Bathrooms - Beautifully Decorated This guest suite has everything you need for a comfy and relaxing stay. Enjoy the 3-person hot tub, perfect for unwinding after a day of adventure. In the summer months, enjoy the heated, in-ground pool. Hiking, beaches and so much more await—and less than an hour’s drive to Chicago. Heated Pool Open from Mid-May to Mid-Oct.

Top guest favorite

A cozy bedroom space features a queen-sized bed adorned with a colorful patterned blanket. Two bedside lamps provide soft lighting. A large window offers views of the outdoors, while wooden walls enhance the rustic charm of the loft.

Farm stay in De Motte

4.96 out of 5 average rating, 202 reviews

Cozy barn loft on organic vegetable farm

Find peace and restoration in this beautiful barn loft at Perkins' Good Earth Farm. The loft has a bedroom, separate shower and toilet spaces, work area, sitting room, kitchen space, and heating/cooling fresh air system. Located above our farm store, the loft provides privacy for you while giving you access to fresh fruits & veggies, locally sourced meats, homemade soups & salads from our farm kitchen, and so much more. You can also walk our farm trails, visit the veggies, or enjoy a campfire.

Home in Whiting

4.95 out of 5 average rating, 133 reviews

MiniGolfHouse-Chicago Close Beach & Indoor Fun!

🌆 30min drive to downtown Chicago ⭐️ Near Horseshoe Casino, Lake Michigan, Whihala Beach, Whoa Zone ⛳️ Heated basement with mini golf, arcade games and big TV 🐶 Pet fee: $150 (Must let us know BEFORE BOOKING if bringing a pet) ⭐️ Close To: Wolf Lake, Indiana Dunes, HardRock 🏠 cots, air mattress, futon sofa in basement 🍼 pack & play, high chair avail ❤️ Guests love: -short drive into Chicago -comfortable beds -indoor mini golf -nearby shops & food -heated bidet toilet seats

Top guest favorite

A spacious living area features a light-colored sectional sofa adorned with soft pillows, positioned beside a wooden coffee table. A decorative area rug adds warmth to the hardwood floor. Natural light enters through a window, complemented by dark curtains. A potted plant and lamps provide additional light.

Home in Munster

4.95 out of 5 average rating, 101 reviews

Entire home: Private, Cozy Oasis in a Quiet Locale

30 minute drive from Chicago's Grant Park. Near Little Calumet and Monon trails. Appeals to nature enthusiasts, cyclists, remote workers and brewery aficionados. This 2 bedroom, 1 bathroom retreat offers comfort and convenience. Full kitchen, private backyard and comfortable living space. 3 casinos, 6 breweries: 3 Floyds, 18th Street, Fuzzyline, Byway, New Oberpfalz & Wildrose within 7 to 20 min drive. Early check-ins offered/subject to availability. Feel free to inquire on availability.

A modern kitchen features sleek white cabinetry and stainless steel appliances. A central island serves as a dining space, complemented by two navy blue stools with gold accents. Pendant lights provide illumination, enhancing the contemporary feel of the room.

Home in Chicago

4.88 out of 5 average rating, 156 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

Whether your looking to stay near family or be close to Downtown. This place has it ALL! This coach house is located in Mt greenwood which is one of the safest neighborhoods in the City of Chicago. It is home to many police, firefighters and teachers. Downtown is a quick 30 minute drive and there are also many bars and restaurants in walking distance. The home has been totally renovated and stocked with all the essentials. All you need to do now is pack your bags and enjoy your vacation.

A spacious living area features a comfortable sofa and a grand piano, complemented by a decorative area rug on polished wooden floors. A window allows natural light to illuminate the room, and a small bookshelf adds a touch of warmth. A small dog with a scarf rests nearby.

Home in Homewood

4.93 out of 5 average rating, 101 reviews

Boulderstrewn: Historic Homewood home

Charming and historic Sears Catalog House on 2/3 acre wooded lot. Less than 10 minute walk to shops and restaurants in downtown Homewood to Metra rail (and Amtrak) station with express service to Hyde Park and University of Chicago (less than a half hour) and Chicago's 3 magnificent downtown waterfront stations (~40 minutes). Fire pit in yard can be used to enjoy summer nights. No cable, but several digital antenna channels available as well as Netflix, XBox and DVDs.

A cozy living area is displayed with a pair of beige sofas, accented by decorative pillows. Framed wall art complements the decor. A soft rug is positioned on the wooden floor, while a lampshade on a side table adds subtle illumination.

Home in Blue Island

4.82 out of 5 average rating, 214 reviews

Warm and comfortable inviting Suburban home !

160 year old land mark community, Framed cedar bevel siding 2 story home, front porch , 10 ft high ceilings, kitchen canned lighting home. 6 feet fence In closed yard, whole house water filtration system , Quite neighborhood with sidewalks . 19 miles to downtown Chicago , Metra train station and bus route, in walking distance . driving to the city of Chicago 5 minutes to major expressways . Host is willing to be available for any and all information 24/7.

A well-appointed bedroom features a spacious bed adorned with a soft blush and white blanket. A bedside lamp and decorative elements are present. Natural light filters through a window dressed with sheer curtains, creating a cozy ambiance. A small chair complements the interior design.

Apartment in Hammond

4.85 out of 5 average rating, 163 reviews

Plant MOOD FREE Wi-fi, parking, washer & dryer!

LATE CHECK-IN guest are welcome!!!! PLEASE READ MY FULL AIRBNB LISTING PRIOR TO BOOKINGS!!!! This special place is close to everything, making it easy to plan your visit. • I80, 294, 94 highways/tolls, etc. • Chicago • Shopping galore • A fun array of restaurants AND A LOT OF FREE PARKING!!! I’m extremely close to MUNSTER, HIGHLAND, SCHERERVILLE, DYER and many more Indiana locations! I’m extremely close to LYNWOOD, LANSING, CALUMET CITY, and many more!

The exterior of a private guest house is shown, featuring a detached two-story structure. A driveway leads to a garage with a white door, while a wooden staircase ascends to the entryway. The surrounding area includes greenery and paved walkways.

Guest suite in Crown Point

4.94 out of 5 average rating, 252 reviews

IT'S THE WRIGHT PLACE

Private guest house newly remodeled. One bedroom queen bed, bath w/shower, full kitchen stocked, including microwave and Keurig coffee maker pods included, family room TV, and WIFI. No matter if you are in town for work, sport competition, family or just vacationing we offer all the comforts of home. Air Mattress available upon request. Please treat as your own home, follow all house rules. No party or gatherings. This is a no smoking home.

Top guest favorite

A cozy living area is featured with two large windows allowing natural light to fill the space. A hanging chair adds a unique touch, while a dark sofa and a coffee table sit on a patterned rug. A television is positioned on a stand nearby.

Apartment in Blue Island

4.94 out of 5 average rating, 308 reviews

Charming Unique 2 Bdrm Apartment in Victorian Home

My place is close to the excitement and culture of the beautiful city of Chicago. It is a short walk to Metra trains with a 25 minute ride downtown. You’ll love my place because of the diverse, comfortable, quiet, tree lined neighborhood where you can relax and feel secure. It is close to expressways, golf courses and a local park with walking path. The apartment is not available to guests without previous positive reviews.

Top guest favorite

A natural pathway leads to a charming safari yurt, adorned with greenery and decorative elements. A wooden archway introduces the entrance, while a nearby barrel sauna complements the serene outdoor setting, surrounded by trees and mulch landscaping.

Yurt in Homewood

4.98 out of 5 average rating, 122 reviews

Glamping Yurt&RV Gaming Room Pool/Hotub/Court more

GLAMPING FUN! April - mid Nov RV w/bathroom - 2 beds 20' Safari Yurt - 4 beds Gaming Room w/bathroom queen & sofa sleeper Xbox Series X & PS5 Gazebo w/2 twin beds (seasonal) Outdoor wooden Barrel-Sauna 27' above ground Pool 6-7 Person outdoor hot-tub Fresh Eggs (seasonal) mini golf 3-n-1 Court; Event Yurt add on $180 up to 15 additional non/overnight guest Contact me for Fall/Winter Glamping no more than 10

A cozy living area features a gray sofa adorned with decorative pillows, flanked by two lamps on white side tables. A set of colorful chairs is positioned around a small coffee table. Natural light enters through large windows, creating a bright and inviting space.

Apartment in Chicago

4.82 out of 5 average rating, 109 reviews

Ultra Modern Beverly Suite

This stylish place to stay is perfect for any event. 420 friendly. Come and let us pamper you. Come and enjoy are tree lined community in the historical Beverly area. This Suite has all the latest amentities and beautifully furnished. The whole group will be comfortable in this spacious and unique space.

Vacation rentals for every style

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Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Homewood family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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 Lincoln Square

4.88 out of 5 average rating, 329 reviews

Private Coach house near Lincoln Square!

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

4.95 out of 5 average rating, 142 reviews

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

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.

Guest suite in Riverwoods

4.95 out of 5 average rating, 427 reviews

Master qtr close to nature & easy urban facilities

The open living area features large floor-to-ceiling windows framing views of the surrounding woods. A sleek two-tone sofa and modern armchairs are arranged near a minimal table. Warm wooden flooring complements the contemporary design, and a staircase leads to the upper level.

Home in Beverly Shores

4.96 out of 5 average rating, 229 reviews

Secluded Modern Retreat Near Beach - "Sandlot"

Top guest favorite

A clear, geodesic dome is set on a paved patio surrounded by a grassy area and decorative plants. The backdrop features a tranquil lake and lush trees, illuminated by a colorful sunset sky.

Guesthouse in Valparaiso

4.98 out of 5 average rating, 108 reviews

Unique Dome Retreat by Indiana Dunes w/ Lake View

A spacious spa room features a modern two-person jacuzzi, surrounded by elegant marble walls. The jacuzzi is designed with a clear accent panel, and amenities such as towels are neatly arranged nearby, promoting a calming and relaxing environment.

Home in Whiting

4.85 out of 5 average rating, 171 reviews

The Spa of Downtown Whiting

The tranquil surface of Flint Lake reflects a colorful sunset, with soft hues of pink and orange blending into the serene blue sky. The surrounding tree line is silhouetted against the fading light, creating a peaceful and calming atmosphere.

Cottage in Valparaiso

4.93 out of 5 average rating, 430 reviews

The Lake Escape -Cozy Lakefront Cottage Valparaiso

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

4.97 out of 5 average rating, 139 reviews

Belmont Pleasures - hot tub / arcade gaming room

Family- and pet-friendly home rentals

Top guest favorite

A tranquil lake scene is depicted, featuring autumnal trees reflecting vibrant hues of yellow, orange, and red in still water. The grassy shoreline enhances the serene environment, while neighboring greenery contributes to the picturesque landscape.

Guest suite in Naperville

4.96 out of 5 average rating, 467 reviews

Cozy Lakeview Studio with Private Access

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

4.91 out of 5 average rating, 196 reviews

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

Top guest favorite

A welcoming open concept living space is portrayed, featuring a comfortable sofa with decorative pillows. A dining area with a table for six sits adjacent to a kitchen with modern appliances. A functioning fireplace adds charm, while a large TV is mounted on the wall.

Home in Manteno

4.95 out of 5 average rating, 249 reviews

Manteno Luxury Comfy Cozy home with- 2 king beds!

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

4.91 out of 5 average rating, 131 reviews

1920s fully updated unique open artist loft space

A walkway lined with pavers is framed by greenery, leading toward a fenced yard. Soft string lights illuminate the area beside the tiny house, creating a serene evening atmosphere. A cozy seating area is visible, inviting relaxation outdoors near the lush foliage.

Tiny home in Burr Ridge

4.9 out of 5 average rating, 402 reviews

Less is more! Pet friendly Tiny Home near Chicago!

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

4.86 out of 5 average rating, 139 reviews

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

A welcoming living area is highlighted by a navy blue sofa positioned beside a decorative plant. A round coffee table rests atop a patterned area rug featuring shades of blue and yellow. Light-colored walls and large windows enhance the brightness of the space.

Home in Homewood

4.92 out of 5 average rating, 66 reviews

Charming Homewood Away from Home

Top guest favorite

A spacious living room features three large windows allowing natural light to fill the space. Comfortable seating includes a leather couch and an armchair. A television is mounted on the wall, and a decorative area rug lies beneath a wooden table set for dining.

Condo in Noble Square

4.97 out of 5 average rating, 840 reviews

Great location. Free parking.

Family-friendly home rentals with a pool

Home in Highland Park

4.91 out of 5 average rating, 148 reviews

2-Acre Highland Park Retreat with Heated Pool ~ 5*

Top guest favorite

Home in Schererville

4.93 out of 5 average rating, 73 reviews

Comfy 3BR 2BA, Liv+Fam Rm, Prime, 3-Car Parking

Top guest favorite

A private cottage is surrounded by lush greenery and features a wooden deck adorned with several blue planters. Steps lead up to the entrance, which is framed by large windows allowing natural light to fill the interior.

Guesthouse in Valparaiso

4.95 out of 5 average rating, 218 reviews

Private Cottage in Gated Nudist Community

The living area features a comfortable sofa adorned with patterned cushions, accompanied by a stylish coffee table. A modern dining setup is visible in the background, along with sleek kitchen cabinetry. Light from overhead fixtures illuminates the open layout with dark hardwood flooring.

Condo in Evanston

4.96 out of 5 average rating, 102 reviews

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

A bright living area features a comfortable gray sofa and two modern chairs set around a round coffee table. Large windows provide expansive views of the city, while greenery adds a touch of nature to the space. The warm lighting creates a welcoming ambiance.

Apartment in Chicago Loop

4.75 out of 5 average rating, 271 reviews

Stunning 3BR Penthouse in the Loop | Roof Deck

Top guest favorite

Apartment in Near North Side

4.95 out of 5 average rating, 101 reviews

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

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

4.9 out of 5 average rating, 553 reviews

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

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

4.9 out of 5 average rating, 109 reviews

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

Quick stats about vacation rentals that are family-friendly in Homewood

Total rentals
30 properties
Nightly prices starting at
€ 112 before taxes and fees
Total number of reviews
1K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi

Destinations to explore