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Family-friendly vacation rentals in Homewood

Find and book unique family-friendly homes on Airbnb

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Homewood family-friendly rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Family-friendly home rentals with a hot tub

Guest favorite
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

Guest favorite
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

Guest favorite
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
4.96 out of 5 average rating, 263 reviews

Tea Studio in Wicker Park Spring Factory

Guest favorite
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"

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, 191 reviews

The Studio at the Dunes

Guest favorite
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, 167 reviews

The Spa of Downtown Whiting

Guest favorite
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, 422 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, 134 reviews

Belmont Pleasures - hot tub / arcade gaming room

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Family- and pet-friendly home rentals

Superhost
Home in Chesterton
4.81 out of 5 average rating, 324 reviews

South Shore Studio Apartment {National Park}

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
4.95 out of 5 average rating, 455 reviews

Cozy Lakeview Studio with Private Access

Guest favorite
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, 190 reviews

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

Superhost
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

Superhost
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, 363 reviews

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

Guest favorite
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, 388 reviews

Miller Mermaid Suite-100 yds from the beach!

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Family-friendly home rentals with a pool

Guest favorite
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, 64 reviews

Cozy house in Schererville

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, 212 reviews

Private Cottage in Gated Nudist Community

Guest favorite
Condo in Evanston
4.96 out of 5 average rating, 112 reviews

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

Guest favorite
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

Top guest favorite
Home in Crown Point
5 out of 5 average rating, 54 reviews

Little Pink House Downtown

Guest favorite
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, 541 reviews

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

Guest favorite
A modern kitchen is showcased with sleek white cabinetry and stainless steel appliances. An island with bar seating is positioned in the foreground, while a spacious archway leads to an elegantly designed hallway featuring artwork and natural light.
Home in Plainfield
4.94 out of 5 average rating, 84 reviews

Relaxing Spanish style Home (w/inground pool)

Guest favorite
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)

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

  • Total rentals

    30 properties

  • Nightly prices starting at

    ﺩ.ﺇ477 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