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Family-friendly holiday rentals in Oak Park

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Oak Park

  • Total holiday rentals

    Explore 150 holiday rentals in Oak Park

  • Nightly prices starting at

    Oak Park holiday rentals start at $64 SGD per night before taxes and fees

  • Verified guest reviews

    Over 11,620 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

  • Wifi availability

    150 of Oak Park holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Oak Park rentals

  • 4.8 Average rating

    Oak Park stays are highly rated by guests – averaging 4.8 out of 5!

Top-rated family-friendly rentals in Oak Park

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

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Top guest favourite
Flat in Oak Park

Spacious & Modern Treetop Oasis King Bed + Parking

Take a deep breath and relax in this airy and bright top floor apartment. Treetops surround the newly renovated and spacious home in a premier Oak Park location. 20 min. to downtown Chicago. Only 1/2 block to the FLW Home & Studio. Walk to dining & train. 2 bedrooms & 1 bath w/tub & shower. Open living/dining/kitchen/sunroom. Cook’s kitchen w/huge island. Primary w/king bed + deep closet. 2nd bdrm w/built-in bunk beds + desk + balcony. Private entry & deck. Shared fenced yard. Driveway parking.

4.98 out of 5 average rating, 102 reviews
Top guest favourite
The living room is bright and spacious, featuring a comfortable seating area with a sofa and two armchairs. A coffee table is centered on a plush area rug, while natural light enters through multiple windows adorned with light curtains. Decorative artwork complements the warm color scheme.
Flat in Oak Park

SuperHost and Super Location Central OP

4.98 Star Superhost rating for this ideal Centrally-located, light, bright, spacious 2 bedroom 1 bath 2nd floor unit in a beautifully updated vintage building! Central air and forced air heat, hardwood floors throughout. Wonderful floor plan to enjoy your stay while you are "in", Near public transportation when you want to "be on the go"! Designated work space, high speed WIFI and 1 parking space on premises. Deck off the kitchen.. Keyless access. 1 King/ 1 Queen bed.Owner lives on the 1st floor

4.98 out of 5 average rating, 149 reviews
Superhost
A spacious living area is highlighted by a black sofa facing a light-colored coffee table. A vibrant area rug adds color underfoot. The walls are adorned with colorful vinyl records and framed artwork, while original woodwork details frame the open layout leading to the dining area.
Flat in Oak Park

Rockin' 2Bed steps to shops/food/train

This musically-inspired vintage 2 BR is perfectly placed in Oak Park and we know you'll have a rockin' vacation here. Steps to shops, cafes, train, and FL Wright home. With a cassette wall, reading nook, and many other cute touches. The apartment is a vintage brownstone with charming details, like original woodwork. Street parking available. Easy access to Chicago.The place is an older Chicago brownstone, with a lived-in feel. NO PARTIES!! Upstairs neighbors can be heard walking and moving

4.87 out of 5 average rating, 794 reviews
Superhost
A spacious bedroom is furnished with a large bed featuring a gray and white patterned blanket. Art pieces are displayed on the wall above the bed, and two bedside lamps with warm light sit on either side. A bold, geometric area rug adds texture to the space.
Guest house in Oak Park

Gallery Loft of Oak Park #1 Top Host in IL

Gallery Loft of Oak Park <a href="https://news.airbnb.com/the-number-one-new-host-in-each-us-state/">2021 #1 Top Host in Illinois</a> is a Chicagoland gem near the birthplace of Ernest Hemingway, Frank Lloyd Wright Home/Studio. 2nd story flat furnished in vintage mcm style, featuring local artists. Walking distance to live music (Fitzgerald's, Friendly Music Community), and restaurants. Firepit access, easy street parking and kitchen well stocked. Private porch. Perfect long/short term stays.

4.91 out of 5 average rating, 269 reviews
Top guest favourite
A bright living area with a sloped ceiling features a comfortable blue sofa and light-colored armchairs. A small marble-top table is set with two cups. A desk is positioned near a window, and a decorative rug adds warmth to the hardwood floor.
Guest house in Oak Park

Oak Park cozy carriage house-lovely, walkable area

Our comfortable, stylish retreat has everything you need to relax and recharge. Whether you are visiting to explore all that beautiful Oak Park and downtown Chicago offer or desire a peaceful space to work. -> Quiet, walkable street near popular cafes, restaurants, taverns, parks, historic homes -> Steps from the "L" Blue Line Oak Park station -> Stocked w/ snacks + gourmet coffee/tea set-up (grinder, AeroPress, and Keurig) -> Onsite off-street parking -> A/C + heat -> garden sitting area

4.97 out of 5 average rating, 141 reviews
Guest favourite
A bright living room features multiple windows allowing natural light to fill the space. A yellow armchair and a dark sofa are arranged around a central wooden table. A decorative rug adds warmth to the hardwood floor, complemented by a lamp and an entertainment unit.
Flat in Oak Park

Top floor of Historic Oak Park Home /2 Car Garage

Secluded but never isolated; 3 blocks from the L-line, next door to Hemingway's birthplace, surrounded by dozens of Frank Lloyd Wright homes, 30 min from the Loop, MDW and ORD, makes this location an ideal platform for the cultural explorer. Experience an ambiance that supports the work-from-home Urban Professional, combining it with a multibedroom layout designed to accommodate family and friends. Gig-speed internet supports sophisticated professional and gaming applications.

4.96 out of 5 average rating, 127 reviews
Top guest favourite
A lush garden surrounds a charming historic home, with greenery and flowers creating a vibrant landscape. A shaded seating area is provided under an umbrella, offering a space for relaxation amidst the natural beauty. The home is partially covered in climbing vines, enhancing its character.
Flat in Oak Park

Studio Apartment in Oak Park

Nestled in Oak Park's historic district, this charming studio apartment is within walking distance of cafes, shops, restaurants, a movie theater, and the CTA/Metra for city and suburban excursions. Featuring a comfortable queen-sized bed, a newly updated full bathroom, and a kitchenette, it sits mere steps from Ernest Hemingway's childhood home and a few blocks from Frank Lloyd Wright's residence and studio. Enjoy the serenity of this historic home and its hidden garden oasis.

4.96 out of 5 average rating, 137 reviews
Superhost
The living area features a comfortable white leather sofa and a reclined chair beside a light wood table. Natural light streams through triple windows adorned with blinds. A decorative fireplace and a wall-mounted TV enhance the space's functionality.
Flat in Oak Park

Chicago-Style, Vintage, Cable & NFL PASS 42-1

→ Introducing our newly renovated and furnished apartment unit nestled in the charming Oak Park Art District. Richly characteristic brick building, Chicago style, situated in a safe and quiet neighborhood. ★ Property Features: • One block away: Oak Park Art District • Vintage Chicago style brick building • Safe, quiet neighborhood • Newly renovated and furnished • Smart TV with Cable • Free Laundry Room • Free Parking for short stays, long stays limit spots please confirm.

4.87 out of 5 average rating, 467 reviews
Top guest favourite
A charming Victorian home is showcased, featuring a front porch with wide steps leading to a door framed by lush greenery. The exterior is painted in a crisp white, complemented by dark accents on the windows. A manicured lawn adds to the inviting landscape.
Home in Oak Park

Oak Park Victorian by FLW Studio

Discover historic charm in our updated 4-bedroom Victorian home in the iconic Frank Lloyd Wright district. Comfortably sleeps 8. Features a fully equipped kitchen, dedicated workspace, and modern amenities. Perfectly located for exploring local gems on foot or a quick 15-min drive to downtown Chicago. Enjoy private parking and easy access to public transit. Ideal for families and groups seeking a stylish, central retreat.

4.96 out of 5 average rating, 148 reviews
Guest favourite
Home in Oak Park

Steps to Shops, Restaurants, Trains; 5BR, 14 Guest

Experience a spacious, pet-friendly 5-bedroom, 3-bath home in vibrant downtown Forest Park, perfect for family gatherings or group vacations. Comfortably sleeps up to 14 guests. Enjoy stylish interiors, a fully equipped kitchen, private outdoor spaces, and easy walkability to Madison Avenue's dining and shops. Convenient access to Chicago trains and private parking for 4 vehicles make this an ideal retreat.

4.89 out of 5 average rating, 141 reviews
Top guest favourite
A historic Queen Anne home features a distinctive turret and a wraparound porch, surrounded by lush greenery. The exterior showcases a blend of siding and masonry with intricate architectural details reflective of its 1889 origins.
Flat in Oak Park

Victorian Charm in Historic Oak Park Free Parking

This historic Queen Anne home built in 1889 is in the heart of Oak Park. Centrally located and within walking distance to all tourist attractions, public transportation, great restaurants, boutiques and grocery stores. It’s the perfect base for exploring Oak Park and Chicago Perfect for long-term stays. We kindly ask that you read our full listing description and our house rules prior to booking.

4.98 out of 5 average rating, 278 reviews
Top guest favourite
A cozy living area features a light-colored sofa and a soft lounge chair, positioned around a low table. Natural light enters through large windows adorned with sheer curtains, illuminating the wood flooring and a colorful area rug.
Townhouse in Oak Park

Lovely Central Oak Park TH w/parking & on Green el

Great central Oak Park location, close to everything including dining, Green Line, Metra, and OPRF High School. Enjoy farm fresh produce, eggs, and cheese or pick up some famous Farmers Market Donuts from the Oak Park Farmers Market just steps out your front door every Saturday May-October. Free (driveway) parking for one car. Backyard & deck space off the kitchen.

4.98 out of 5 average rating, 247 reviews

Popular amenities for Oak Park family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favourite
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

4.87 out of 5 average rating, 103 reviews
Superhost
A spacious studio is showcased with a king-size bed positioned against a contrasting dark wall. Natural light filters through large windows, highlighting the exposed brick and the vintage stone fireplace. A mirrored wall accents the room, while a desk complements the seating area.
Apartment in Little Italy

Private hot tub - King bed suite - Free parking

4.92 out of 5 average rating, 283 reviews
Guest favourite
The exterior of the home features a warm brick façade, large front windows allowing natural light to fill the interior, and inviting steps leading to a decorative front door. Lush greenery and potted plants enhance the welcoming atmosphere of the entrance.
Home in Humboldt Park

H&H 1896 - Spacious, Fully Stocked, & Free Parking

4.95 out of 5 average rating, 120 reviews
Guest favourite
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.
Guest house in Chicago

Private Coach house near Lincoln Square!

4.88 out of 5 average rating, 398 reviews
Top guest favourite
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*)

4.94 out of 5 average rating, 898 reviews
Guest favourite
A spacious living area features floor-to-ceiling windows that showcase panoramic views of the Chicago skyline. Modern furnishings include a comfortable sectional sofa and an elegant coffee table. A dining area is visible in the background, complemented by sleek decor and ample natural light.
Flat in West Town

Top of River West: Luxe Penthouse for Groups

4.89 out of 5 average rating, 141 reviews
Guest favourite
A spacious living room features comfortable seating on soft gray furniture, including a large chaise and armchairs. Natural light brightens the area, while a gas fireplace is set within a stylish stone surround. A large flat-screen TV is mounted above the fireplace.
Home in Lake View

Entire house in Lakeview with yard and garage

4.86 out of 5 average rating, 111 reviews
Top guest favourite
The living area features a spacious couch accompanied by two armchairs, all positioned around a circular dining table. A large window allows natural light to illuminate the space, adorned with potted plants and modern artwork that adds a touch of style.
Apartment in Ukrainian Village

Ukrainian Village 3BR/3BA • Private Patio, Parking

4.98 out of 5 average rating, 128 reviews

Family- and pet-friendly home rentals

Guest favourite
Flat in Oak Park

Bright & Gorgeous- 5* Location- Queen Beds - Pkg

4.87 out of 5 average rating, 155 reviews
Top guest favourite
A comfortable living area features a light gray sofa adorned with colorful pillows. A small wooden coffee table with intricate designs sits in front of the sofa, accompanied by a floral arrangement. Art pieces hang on the walls, and natural light enters through the large window.
Flat in Oak Park

Cheerful Remodel Prime Location

4.92 out of 5 average rating, 155 reviews
Guest favourite
A spacious living area features a modern sectional sofa in neutral tones. A sleek television is mounted on the wall opposite a minimalist coffee table. The adjoining dining area, visible through an archway, includes a round table with four chairs.
Flat in Forest Park

Burkhardt Ct. Upstairs.

4.87 out of 5 average rating, 407 reviews
Top guest favourite
A spacious bedroom features a large bed with dark bedding and decorative pillows. A wooden bookshelf filled with books stands against one wall, while sunlight filters through a window adorned with light curtains. A vintage dresser and bedside table complete the welcoming space.
Flat in Forest Park

Like a Treehouse!

5.0 out of 5 average rating, 394 reviews
Guest favourite
A cozy living room features four plush purple chairs arranged around a circular table. A modern television is mounted above a white brick fireplace, complemented by bookshelves filled with various items. A large potted plant adds a touch of greenery, enhancing the warm atmosphere.
Home in Oak Park

A Comfortable Stay While You are Away in Oak Park

4.88 out of 5 average rating, 106 reviews
Guest favourite
A charming three-story building is shown with a covered front porch and steps leading to the entrance. The façade features light beige stucco and dark accents, with large windows that allow natural light to flow in. Lush greenery surrounds the entrance, contributing to a welcoming setting.
Flat in Oak Park

Cozy modern unit w/ easy access to downtown Chi

4.8 out of 5 average rating, 208 reviews
Guest favourite
A comfortable living area features a blue couch adorned with decorative pillows, complemented by a lighted lamp on a small side table. Two chairs are positioned nearby, and a patterned area rug covers the hardwood floor, while natural light filters through the windows.
Home in Forest Park

Adorable house Madison Street w/ 2 car garage!

4.88 out of 5 average rating, 147 reviews
Guest favourite
A spacious living area showcases a comfortable gray sectional sofa and a reclining chair. A contemporary coffee table rests on an area rug with floral patterns. A mounted TV is visible alongside a wooden credenza featuring a coffee maker and supplies, enhancing the functionality of the space.
Home in Forest Park

Gather in Spacious 3 Bedroom 2 Bath Retreat

4.97 out of 5 average rating, 188 reviews

Family-friendly home rentals with a pool

Top guest favourite
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

4.98 out of 5 average rating, 172 reviews
Guest favourite
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.
Apartment in Elk Grove Village

Just remodeled apartment close to airport and mall

4.91 out of 5 average rating, 128 reviews
Guest favourite
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

4.93 out of 5 average rating, 131 reviews
Guest favourite
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

4.96 out of 5 average rating, 147 reviews
Superhost
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 The Loop

Spectacular 2BR Penthouse in the Loop | Roof Deck

4.81 out of 5 average rating, 360 reviews
Top guest favourite
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.
Flat in Downtown Chicago

The Executive's Escape (Fitness Center • Sauna)

4.9 out of 5 average rating, 146 reviews
Guest favourite
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.
Flat in Uptown

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

4.9 out of 5 average rating, 600 reviews
Guest favourite
A spacious bedroom features large floor-to-ceiling windows, allowing natural light to fill the room. A large bed with neutral bedding is complemented by a contemporary desk and chair setup, which is arranged near a wood-framed lamp. A subtle area rug lies beneath the bed.
Flat in Downtown Chicago

50th Floor Mag Mile Views, Balcony, Pool, Gym

4.9 out of 5 average rating, 143 reviews

When is the best time to visit Oak Park?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$191 SGD$193 SGD$208 SGD$218 SGD$246 SGD$266 SGD$245 SGD$238 SGD$223 SGD$227 SGD$213 SGD$213 SGD
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