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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

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, 193 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.

A collage of the Mini Golf House showcases the vibrant mini golf area, a cozy lounge with arcade games, a comfortable sleeping space, and a living area featuring a large TV. The layout highlights inviting spaces designed for entertainment and relaxation.

Home in Whiting

4.96 out of 5 average rating, 124 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

The exterior of the barn apartment is shown, featuring a rustic wooden façade with large glass windows. The surrounding lawn is lush and green, with a covered porch and outdoor seating area visible. A vintage Airstream is parked nearby, adding charm to the landscape.

Barn in Valparaiso

5 out of 5 average rating, 195 reviews

The Good Farm: Barn BnB on 44 acres near Lake Mich

Enjoy 44 acres just 15 minutes from the beaches of Lake Michigan! With room to sleep 6, guests will enjoy this fully stocked barn apartment with gorgeous views! You'll be near Indiana Dunes National Park, tree-lined hiking/biking trails, wineries, cafes, outlet malls, & antique shops. Roast s'mores in the fire pit, watch chickens free range through the yard or grab a bite to eat downtown Valpo/Chesterton/MC—the perfect getaway for families or friends who want to relax or adventure in nature.

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

4.97 out of 5 average rating, 118 reviews

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

GLAMPING FUN! April - Nov Guest=14 Nov-Mar Guest=10 Safari Yurt not included mid-Fall/Winter RV w/bathroom - 2 beds no water in RV in Winter 20' Safari Yurt - 4 beds Gaming Room w/bathroom queen & sofa sleeper Xbox Series X & PS5 Gazebo w/2 twin beds Outdoor wooden Barrel-Sauna 27' above ground Pool 6-7 Person outdoor hot-tub Fresh Eggs seasonally; Mini Golf 3-n-1 Court; 1 dozen fresh eggs; Event Yurt add on $180 up to 15 additional non/overnight Contact me for Fall/Winter Glamping

A well-maintained exterior view of the cottage is displayed, featuring a neatly manicured lawn and bordered by trees. A private driveway leads to the entrance. The structure showcases a front porch area, and a fire pit is visible in the yard, inviting outdoor enjoyment.

Cottage in Merrillville

4.88 out of 5 average rating, 258 reviews

The Hideaway

This Christian friendly cozy cottage, located 30 minutes from Chicago is located on a private 3 acre property. It’s a private detached cottage from main house that sleeps four. One king size bedroom (2 air mattresses) (sheets supplied), large full bathroom with deep tub w/ handle (towels supplied), full kitchen (dishes, pots and pans ect supplied) private covered parking and yard (directly in front of cottage) w/ its own fire pit for enjoyment. No plug for electric cars (station 2 m away).

Top guest favorite

An open-concept living and dining area showcases modern furnishings. A cozy sectional sofa with decorative pillows is positioned beside a minimalist white coffee table. The dining table, with white chairs, complements the well-equipped kitchen featuring stainless steel appliances and granite countertops.

Home in Cedar Lake

4.99 out of 5 average rating, 103 reviews

The Gray Warbler single family lake view home

Stunning 3 bedroom 2 bathroom home! Breathtaking lake views from all living spaces! Nestled in a serene location this fully remodeled retreat with all brand new furnishings offers a perfect getaway. Comfortable, brand new adjustable base mattresses, clean, modern bathrooms with new tile showers and a tub, well equipped kitchen with new granite counters and stainless appliances open to our living room with 65" HD smart TV and Verizon 5G. Enjoy our arcade with Golden Tee and Mrs. Pac-Man!

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, 208 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, 159 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!

Top guest favorite

A charming single-story home is surrounded by lush greenery and colorful landscaping. The house features a light exterior with dark shutters and a welcoming front porch. A small tree adds a splash of color to the neatly manicured lawn.

Home in Munster

4.95 out of 5 average rating, 115 reviews

Cozy three bedroom home in Munster , Indiana.

Plan your next escape to Indiana or Illinois and stay in this beautifully renovated and thoughtfully appointed 3 bedroom and 1 bath home. Located in the quiet and safe suburb of Munster, Indiana, the property is just a 3 minute, easy access to the I-94 Highway. Exciting Downtown Chicago is just 30 minutes away! Walk to Riverside Park and take in the scenic view while enjoying a morning croissant and coffee from one of the quaint neighbourhood cafés.

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, 248 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, 305 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

Double doors open to a bright living area featuring a leather sofa and a light-colored armchair. A coffee table is placed on a soft area rug, while lamps provide soft illumination. A ceiling fan hangs above, and large windows allow natural light to fill the space.

Home in Manteno

4.98 out of 5 average rating, 198 reviews

Updated, bright, and modern, 3 bedroom home.

You will be comfortable in this newly remodeled three bedroom, two bathroom home. ✶ 6.7Miles to Olivet Nazarene University ✶ 8.4Miles to Riverside Medical ✶ 11Miles to Kankakee River State Park ✶ 43Miles to Midway Airport The home FEATURES: *Safe, quiet, walkable neighborhood *3 Bedroom; 1 King, 1 Queen, 2 twin beds *Spacious fully equipped kitchen with coffee station *Washing Machine, Dryer & Dishwasher * Fast Wi-Fi

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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

An inviting above-ground pool is surrounded by a wooden deck and protective railing. A ladder leads into the water, and a large white inflatable float is positioned nearby. The area is complemented by green grass and trees in the background, creating a tranquil outdoor setting.

Guesthouse in Merrillville

4.91 out of 5 average rating, 128 reviews

Romantic Getaway Guesthouse/ Jacuzzi/Sauna/Pool

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, 135 reviews

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

Top guest favorite

The exterior of a red tiny house is framed by greenery, showcasing a wooden deck with railing. A hot tub is positioned on the deck, while a door and windows illuminate the structure, providing a welcoming atmosphere in a private yard.

Tiny home in Michigan City

4.98 out of 5 average rating, 192 reviews

The Studio at the Dunes

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, 228 reviews

Secluded Modern Retreat Near Beach - "Sandlot"

A spacious dining area is highlighted by a large wooden table with a central plant. Four chairs, upholstered in a muted tone, surround the table. A geometric pendant light hangs above, while a patterned wallpaper adds decorative interest to the room. Natural light enters through a sizable window.

Home in Michigan City

4.91 out of 5 average rating, 175 reviews

Pet Friendly Perfect Summer Getaway with Hot Tub

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

4.86 out of 5 average rating, 169 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, 424 reviews

The Lake Escape -Cozy Lakefront Cottage Valparaiso

Top guest favorite

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 Belmont Cragin

4.98 out of 5 average rating, 135 reviews

Belmont Pleasures - hot tub / arcade gaming room

Family- and pet-friendly home rentals

Home in Chesterton

4.81 out of 5 average rating, 324 reviews

South Shore Studio Apartment {National Park}

A cozy seating area features a comfortable cushion adorned with decorative pillows, including one with the word 'LOVE' and a paw print. Wooden shelves above showcase neatly arranged storage baskets and framed items, while natural light filters in through a nearby window.

Tiny home in Burr Ridge

4.9 out of 5 average rating, 394 reviews

Less is more! Pet friendly Tiny Home near Chicago!

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

4.92 out of 5 average rating, 138 reviews

The Sunshine Spot

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

4.85 out of 5 average rating, 132 reviews

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

Top guest favorite

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

4.99 out of 5 average rating, 365 reviews

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

A cozy living area is furnished with a dark daybed adorned with decorative blue cushions. A bookshelf displays a collection of books, complemented by a woven basket. Two wooden chairs face a circular coffee table, creating a comfortable space bathed in natural light from large windows.

Apartment in Oak Park

4.89 out of 5 average rating, 410 reviews

Restful Retreat Perfectly Located by Train+Shops

A modern kitchen showcases sleek white cabinetry and a large island with seating for three on black stools. Open shelving displays various glassware. A stainless steel range hood is positioned above the gas cooktop, while natural light fills the space through windows.

Apartment in Edgewater

4.99 out of 5 average rating, 145 reviews

Newly Renovated, Spacious 2BR in Andersonville

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 Miller

4.96 out of 5 average rating, 389 reviews

Miller Mermaid Suite-100 yds from the beach!

Family-friendly home rentals with a pool

A living room is displayed featuring a stone fireplace as a focal point. A ceiling fan hangs above a light-colored sofa and a clear coffee table. Dark curtains frame two windows, and a dining table is positioned near the staircase, creating a functional and inviting space.

Home in Schererville

4.92 out of 5 average rating, 65 reviews

Comfortable 3BR Home-Prime Video, WiFi, 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, 212 reviews

Private Cottage in Gated Nudist Community

Condo in Evanston

4.96 out of 5 average rating, 113 reviews

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

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, 13 reviews

Munster hide away

A large outdoor pool features clear blue water surrounded by a spacious deck equipped with numerous lounge chairs. Sunlight reflects off the surface, highlighting the inviting atmosphere, with nearby buildings visible in the background.

Home in Michigan City

4.96 out of 5 average rating, 182 reviews

5 Bedroom Luxury Home In Heart of Beachwalk Resort

Top guest favorite

Home in Crown Point

5 out of 5 average rating, 54 reviews

Little Pink House Downtown

An indoor mosaic-tiled pool is surrounded by a spacious, elegantly arched ceiling. Soft lighting reflects off the water, enhancing the serene atmosphere. Wooden lounge chairs are placed along the poolside, providing a comfortable area to relax.

Apartment in Uptown

4.9 out of 5 average rating, 542 reviews

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

An outdoor pool is featured with a modern design, surrounded by grey tile and lounge chairs. Clear blue water reflects the sky above. Urban buildings rise in the background, providing a cityscape view from the pool area.

Apartment in Near Southside

4.89 out of 5 average rating, 103 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
R2,294 ZAR 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