House holiday rentals in Oak Lawn

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Top-rated house rentals in Oak Lawn

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Guest favourite
A modern living area features a dark leather sofa adorned with blue and cream cushions. A stylish coffee table with geometric design sits atop a decorative area rug. A large black and white photograph of a city skyline is displayed on the wall, complemented by a floor lamp and a side table.
Home in Lower West Side
4.95 out of 5 average rating, 426 reviews

Get Cozy at a Powder-Blue Residence in the Heart of Pilsen

House is perfectly located within walking distance of Pilsen's best attractions. Home is furnished and newly renovated with the idea of making your stay as comfortable as possible. Walking distance from Thalia Hall and many other great restaurants and coffee shops. For your convenience there is a "corner store" steps from the home where you can purchase food and beverage items. The whole apartment is professionally cleaned after every guest no matter how many days they have stayed. Fresh sheets and towels are provided for all guests as well. Walking distance from local favorites: Simone’s, Honky Tonk BBQ, Dusek's/Punch House/Thalia Hall, 5 Rabanitos, Furious Spoon, S.K.Y and HaiSous. Located 2 miles South West of Downtown Chicago. Extremely close to South Loop and West Loop. Amenities: - Washer and Dryer (located in unit) - Granite counter tops - All new appliances - Tiled bathroom - Central Heat/AC - Private back deck  - Closet space All access, full kitchen, washer and drier in apartment. Private entrance with Keyless entry. Available at any time, happy to answer any questions you may have. Interaction will be dictated by guests. This is a vibrant family neighborhood with character, art, great food, and culture. Walk to amazing restaurants, bars, and coffee shops, including local favorites Simone’s, Honky Tonk BBQ, 5 Rabanitos, Furious Spoon, S.K.Y, and HaiSous. Close to major Chicago highways: I-190: Kennedy Expressway I-290: Eisenhower Expressway I-55: Stevenson Expressway I-90/94: Chicago Skyway, Dan Ryan Expressway, Kennedy Expressway, Jane Addams Memorial Tollway Public transit easily accessible: CTA Bus #8, 18, 60 CTA Trains: Blue, Pink and Orange Lines Divvy Bike Rental Station one block away Permit Parking $6-10 dollar Uber to Downtown

Guest favourite
The master bedroom features a spacious bed dressed in soft linens, with a light blanket draped across the foot. A large mirror reflects natural light, and sliding glass doors lead to a private outdoor seating area. Warm hues accompany scenic artwork on the walls.
Home in Ranch Triangle
4.86 out of 5 average rating, 163 reviews

LAVISH LINCOLN PARK Home w/ Patio +attached garage

Escape into this Lincoln Park Hidden Gem! Guests love this home because: - Surrounded by top-notch restaurants/retail - Close to all popular attractions that make Chicago so great - Luxurious, newly-renovated interior filled with natural light - Open-floor plan for entertaining! - Gorgeous master en-suite with marble bath + walkout patio! - Fast WiFi (1000 mbps) - Very comfy beds! - Attached, private garage is huge bonus! - Red line (North/Clybourn) station 0.2 miles away (3-5 minute walk)

Guest favourite
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, 167 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.

Top Guest favourite
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
4.87 out of 5 average rating, 154 reviews

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

Welcome to the Naperville Nest! Rare North Naperville opportunity to find a home suited for the whole family! Pets are more than welcome to enjoy the 1/2 acre fully fenced in yard. This is a a fully updated home minutes from Downtown Naperville, I-88 and many more exciting destinations in the Western Suburbs. You will feel at home whether you're inside or outside...each bedroom has it's own TV and the outdoor living includes natural gas firepit & grill/dining table...this home has it all!

Top Guest favourite
A living room features a mid-century velvet sofa in a rich green hue, paired with a tan leather chair. Natural light streams through large windows, illuminating a glass coffee table and a decorative wall with layered wooden frames. The original brick fireplace adds character to the space.
Home in Berwyn
4.98 out of 5 average rating, 183 reviews

Retro Modern Bungalow | free parking | fire pit

Experience the city in style at Retro Modern Bungalow, the perfect pad for up to 4 friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

Top Guest favourite
A well-lit sleeping area is featuring two spacious beds with crisp white bedding. A dresser is positioned nearby, and a round mirror is mounted on the wall, reflecting natural light from a window. A bold blue accent wall adds a pop of color to the room.
Home in Oak Park
4.98 out of 5 average rating, 168 reviews

Cozy Studio by Train and Highway w/ Parking, for 4

Escape to an enchanting garden studio nestled in Oak Park's famous historic district. Discover our private urban farm with full gardens and 6 cheerful hens. Stroll to charming stores, cafes, and restaurants, or hop the nearby "L" for effortless Chicago adventures. Free parking, easy airport access. This serene, non-smoking studio with a kitchenette requires no check-out chores. No parties, 4 guests max. Booking age, 25 or at least one 5 ⭐️ review. Visit profile for more units.

Guest favourite
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, 104 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 favourite
A stylish living space is highlighted by a brown leather sofa and a large area rug, with natural light streaming through the window. The modern kitchen is equipped with sleek black cabinetry and stainless steel appliances. Potted plants add a touch of greenery to the setting.
Home in Wicker Park
4.97 out of 5 average rating, 272 reviews

Division St Designer Home In Heart of Wicker Park

Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).

Guest favourite
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, 217 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.

Guest favourite
A spacious bedroom features a large bed with a dark blue duvet and an orange-accented blanket. Two nightstands with lamps are positioned on either side, and colorful artwork decorates the walls. Natural light enters through a window, framed by soft, light pink curtains.
Home in Worth
4.85 out of 5 average rating, 161 reviews

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

This beautiful, newly remodeled, spacious, 3 bed 2 bath ranch style home is set back on a large lot. Located close to a major hwy, restaurants and a shopping. Just 15 minute to Midway Airport, 25 mins to O'Hare, and 25 mins to Downtown Chicago. Its a great spot to get to everything! Perfect for families, vacationers, and business travelers. You must be 21 or older to book. You must provide a valid photo of your D.L. or State ID upon request.

Top Guest favourite
A cozy living area features a modern gray sofa adorned with yellow pillows, situated on a patterned rug. A low wooden media console holds a flat-screen TV, while large windows allow natural light to brighten the space. Colorful artwork is displayed on the walls.
Home in Bridgeport
4.96 out of 5 average rating, 262 reviews

Peaceful Modern Full House in Trendy Bridgeport

Kick back & relax in your home away from home in our modern & peaceful space in the heart of the Bridgeport neighborhood. Featuring incredible natural light, modern amenities & beautiful artwork, the house is impeccably clean and designed to ensure you have the best travel experience possible. Located on popular Morgan Street, you're only blocks away from bakeries, farm-to-table restaurants, independent coffee shops and local breweries.

Top Guest favourite
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, 218 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

Popular amenities for Oak Lawn house rentals

Quick stats about house rentals in Oak Lawn

  • Total holiday rentals

    Explore 20 holiday rentals in Oak Lawn

  • Nightly prices starting at

    Oak Lawn holiday rentals start at $52 NZD per night before taxes and fees

  • Verified guest reviews

    Over 480 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Oak Lawn holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Oak Lawn rentals

  • 4.8 Average rating

    Oak Lawn stays are highly rated by guests—averaging 4.8 out of 5!

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