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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

Farm stay in De Motte

4.96 out of 5 average rating, 199 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

4.96 out of 5 average rating, 132 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

An aerial view captures the inviting pool area surrounded by lush greenery. The sparkling blue pool is framed by several lounge chairs, with a shaded patio leading to a well-maintained RV parked near the entrance. Colorful landscaping adds to the serene outdoor setting.

Camper/RV in Porter

4.82 out of 5 average rating, 739 reviews

'Pool Barn Camper' w/Hot Tub near Indiana Dunes

Heated pool open until mid October! Hot tub open all year! Fully equipped RV sleeps 5, has bathroom w/shower, stove, microwave, TV, heat & A/C, & running water all year. Located on the bike trail & only minutes from the sand beaches of Indiana Dunes on Lake Michigan. Hike in the Indiana Dunes National Park along the Little Calumet River & the historic Bailley homestead, only 1 block from the RV. Enjoy our large pool, hot tub, grill, campfire, & playground too. Schedule your visit today!

A comfortable living room features a light-colored sofa and a cozy armchair, paired with a wooden coffee table. A large television is mounted on the wall, and plants are placed on the window sill. Geometric shelves add a decorative touch to the neutral-colored walls.

Home in Chicago

4.88 out of 5 average rating, 154 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.

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.

Top guest favorite

A cozy sleeping nook features a unique, artistic bed framed by flowing fabric. Decorative pillows add comfort, while storage drawers are tucked beneath. A television is mounted on the wall, and a soft area rug runs across the floor, enhancing the inviting layout of the open studio.

Guest suite in Gary

4.96 out of 5 average rating, 397 reviews

Miller Mermaid Suite-100 yds from the beach!

100 yds from the beach, the cozy MERMAID SWEET awaits you and is well suited for a young family or 2-3 adult friends. This artsy basement open studio space includes a private entrance, kitchenette, unique art & a cozy reading/sleeping nook! Enjoy beautiful sunsets from the upstairs deck. BBQ on the grill. Visit local restaurants, shops & galleries. Hike wooded trails & swim by sandy, dune-grass beaches. . House-trained dogs welcome! Sorry no cats (allergies)

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, 162 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, 251 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

Apartment in Blue Island

4.94 out of 5 average rating, 307 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, 121 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

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

Enjoy luxury and comfort in this cozy lakefront studio with a private entrance, attached to a home where the friendly hosts reside. The studio offers a plush queen bed, a kitchenette with a mini fridge, microwave, induction cooktop, and a full bathroom. Located in one of Naperville’s safest neighborhoods, it’s just moments from cafes, restaurants, markets, and a biking trail, with easy access to I-88.

Vacation rentals for every style

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Unique stays

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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, 327 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, 140 reviews

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

A living area features a light-colored sofa arranged around a round wooden coffee table. Large windows with divided panes allow natural light to fill the space, while a decorative rug adds a touch of color. Potted plants are positioned for a natural accent.

Guest suite in Riverwoods

4.95 out of 5 average rating, 426 reviews

Master qtr close to nature & easy urban facilities

Top guest favorite

Tiny home in Michigan City

4.99 out of 5 average rating, 200 reviews

The Studio at the Dunes

A brick building stands on a tree-lined street, featuring a gated entrance and a set of wooden stairs leading to the front door. Lush greenery surrounds the entryway, providing a welcoming touch to the exterior.

Condo in West Town

4.97 out of 5 average rating, 159 reviews

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

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

Large windows provide a scenic view of Flint Lake and a deck area featuring an umbrella and lounge chairs. Soft sunlight filters through the trees, illuminating a cozy seating area adorned with floral cushions.

Cottage in Valparaiso

4.93 out of 5 average rating, 429 reviews

The Lake Escape -Cozy Lakefront Cottage Valparaiso

A hot tub is positioned in a vibrant game room, surrounded by colorful murals depicting a beach and lively graphics. Water glistens in the tub, inviting relaxation and enjoyment after a day of activities.

Apartment in Dunning

4.97 out of 5 average rating, 138 reviews

Belmont Pleasures - hot tub / arcade gaming room

Family- and pet-friendly home rentals

Apartment in Oak Park

4.91 out of 5 average rating, 196 reviews

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

Top guest favorite

The exterior showcases a well-maintained carriage house with a white façade and wooden accents. A small covered porch features two black chairs and a side table, complemented by a gravel path and greenery along the side.

Guesthouse in Valparaiso

4.97 out of 5 average rating, 196 reviews

Cozy Luxe Downtown Valparaiso Stay

Top guest favorite

Apartment in Jefferson Park

4.95 out of 5 average rating, 239 reviews

Entire 1st Floor Apt near O'Hare/ORD & Blue Line

A spacious backyard is surrounded by a wooden fence, featuring a well-maintained lawn. A large tree offers shade, while a set of red outdoor chairs is positioned around a small firepit. A children's playset is visible in a corner, enhancing the family-friendly atmosphere.

Home in Naperville

4.86 out of 5 average rating, 138 reviews

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

A corner jacuzzi whirlpool tub is positioned against a wall, featuring multiple jets for relaxation. A white toilet and a small wooden stool are visible nearby. Light gray walls are complemented by a window covered with a light-colored curtain, allowing natural light to filter in.

Home in Chicago Ridge

4.92 out of 5 average rating, 161 reviews

Quiet cul-de-sac with huge fenced in backyard

Top guest favorite

Condo in Noble Square

4.97 out of 5 average rating, 834 reviews

Great location. Free parking.

A sandy pathway winds through tall grasses, leading to Lake Michigan. The tranquil water reflects the soft hues of the sky, with clouds adding texture to the serene scene. The beach's inviting atmosphere creates a perfect setting for relaxation and exploration.

4.92 out of 5 average rating, 111 reviews

Blue Birdhouse - Indiana Dunes

Apartment in Hegewisch

4.91 out of 5 average rating, 232 reviews

Handicap accessible apartment w/Level-2 EV Charger

Family-friendly home rentals with a pool

Top guest favorite

An outdoor pool is surrounded by wooden decking and a fence, offering a private swimming area. Lush trees provide shade, while a clear sky with soft clouds hangs above. The pool is filled with blue water, and a few inflatable toys float on the surface.

Home in Schererville

4.93 out of 5 average rating, 72 reviews

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

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, 217 reviews

Private Cottage in Gated Nudist Community

An outdoor pool area is shown, featuring a clear blue pool surrounded by lounge chairs. Trees provide a touch of greenery, while a modern glass structure offers shaded seating. Sunshine reflects off the water, creating a bright and inviting atmosphere.

Condo in Evanston

4.96 out of 5 average rating, 100 reviews

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

A modern living area features comfortable seating, including a vibrant yellow chair and a sectional sofa adorned with textured throw pillows. A stylish marble coffee table sits atop a patterned rug, with a large flat-screen TV mounted on the wall. A dining table with blue chairs is visible in the background.

Apartment in Warrenville

5 out of 5 average rating, 4 reviews

Naperville Family Fun! Pool, Pickleball, Kids Room

A spacious living room is featured with a cream-colored sectional couch facing a mounted flat-screen TV. Natural light pours in through large windows adorned with blinds. A stone accent wall adds texture, complemented by two decorative pieces and a ceiling fan.

Home in Munster

5 out of 5 average rating, 14 reviews

Munster hide away

Apartment in Chicago Loop

4.82 out of 5 average rating, 276 reviews

Spectacular 2BR Penthouse in the Loop | Roof Deck

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, 551 reviews

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

Apartment in South Loop

4.9 out of 5 average rating, 108 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
G$27,190 GYD before taxes and fees
Total number of reviews
970 reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi

Destinations to explore