Holiday rentals in Oak Lawn

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Oak Lawn

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Flat in Oak Lawn
4.98 out of 5 average rating, 282 reviews

New by Midway Airport

Located 4 miles away from Midway Airport in Chicago, Seat Geek Stadium 4 miles away, 20min to Down Town, 15min to Amphitheatre in Tinley Park 2-Bathrooms 3-Bedrooms one with queen size bed and 2 bedrooms with 4 single beds can accommodate up to 6 people. Two TV's 4K Incl. NETFLIX & PEACOCK. Whether you're in town on business or for personal reasons our space has been meticulously designed to provide you with the best stay in the area!Digital check-in.This Airbnb operates with Village Ord. 8-875

Guest favourite
A spacious living room is highlighted by a sectional sofa adorned with orange and white cushions. A round wooden coffee table complements an accent chair, while a tall plant adds a touch of greenery. Natural light filters through the sheer curtains, enhancing the neutral decor.
Home in Burbank
4.94 out of 5 average rating, 88 reviews

4BR/2BA + Fenced Backyard + Garage + Near MDW

Unwind in style at our stunning Burbank home! With its modern, ultra-cool vibe and sensational light fixtures this house is the perfect retreat after a day of adventures. Conveniently located near Midway Airport✈️ and public transportation 🚍 and just a short Uber ride to downtown Chicago 🌆 you'll enjoy the perfect blend of convenience, comfort, and cool + enjoy free garage and driveway parking for added convenience. 🚗 Come experience the best of Burbank – book now for an unforgettable stay!

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
4.87 out of 5 average rating, 175 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
A spacious living area features a corner sectional sofa with soft cushioning and a cozy throw. Large windows provide natural light and city views. A simple coffee table sits in front, with light-colored carpet underfoot, enhancing the comfortable atmosphere.
Flat in Aurora
4.98 out of 5 average rating, 263 reviews

Penthouse In The Historic Hobbs

Experience luxury and historic charm at the Penthouse in the Historic Hobbs. Built in 1892, and restored in 2023, this new one bedroom corner unit offers a panoramic view of the Aurora skyline. Cook a delicious meal in the fully stocked kitchen. Dine at the bespoke table in the window bay under the iconic onion dome. Relax on the cozy sofa and enjoy a movie on the big screen TV. Rest in the plush king-sized bed. This urban retreat is near coffee, shopping, art and entertainment.

Top guest favourite
A spacious dining area features a large wooden table with comfortable upholstered chairs, accommodating multiple guests. An elegant light fixture hangs above, providing soft illumination. The room connects seamlessly to the living area and kitchen, enhancing the open-concept design.
Bungalow in Beverly
4.95 out of 5 average rating, 40 reviews

Beverly Hills of Chicago Luxury Guest Favorite

Escape to luxury in this beautifully designed 5 bedroom, 3.5-bath home in Chicago's prestigious Beverly Hills neighborhood. Spacious living and high-end finishes, full finished basement have fun with air hockey, pool table, and video gaming, this entertainment space is for guests of all ages. Unwind on the private deck or enclosed front porch. explore retail shops and upscale dining. Metra train station provides a quick 15 minute downtown Chicago area. Close to downtown Chicago!

Guest favourite
A bright living area features a blue sofa, two armchairs, and a stylish coffee table in the center. Large windows allow natural light to fill the space, revealing a view of the outside. A decorative rug adds warmth to the wooden floor.
Home in Homewood
4.94 out of 5 average rating, 47 reviews

Homewood Oasis

Welcome to our Homewood Oasis, where relaxation meets family fun! As former residents of this charming town, we know the importance of a comfortable and enjoyable stay when coming back to visit. Our Airbnb is more than just a place to sleep; it's a carefully curated space designed for families like yours. As hosts who've experienced the need for a home away from home, we've put our heart into making this space welcoming and enjoyable for you. We look forward to hosting you!

Guest favourite
A round dining table is set with blue dishware and a floral centerpiece. Four light-colored chairs surround the table, placed on a patterned area rug. Natural light is visible through two softly shaded windows, and a tall green plant adds a touch of greenery to the room.
Flat in Beverly
4.93 out of 5 average rating, 121 reviews

Beverly Cottage Loft

Whether you're looking to stay near family or be close to downtown, our place has it all. This tranquil cottage is located in Beverly which is one of the safest neighborhoods in the city of Chicago. Downtown is a quick 20 minute drive and there are also many restaurants and bars in this area. This cottage has been renovated and have all the essentials you need. All you need to do is unpack your bags and enjoy your vacation. The space is modern, clean, and cozy.

Superhost
Home in Worth
4.85 out of 5 average rating, 178 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.

Superhost
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
4.89 out of 5 average rating, 199 reviews

Quiet cul-de-sac with huge fenced in backyard

3 bedroom, 2 bath ranch home on a quiet cul-de-sac. Big fenced in backyard for the kids, dog, & adults to play during the day, then relax by the fire at night. Walking distance (50 ft.) to the bar/restaurant with private entrance. 15 miles (25 mins) from downtown Chicago. And for you couples, come back home from your busy day, sit back and relax in the 8 jet jacuzzi whirlpool tub that will comfortably fit both of you.

Guest favourite
A modern living area is furnished with a gray sofa and two light-colored armchairs. A round coffee table sits in the center, accompanied by a small plant. Natural light filters through a large window, enhancing the room's clean, welcoming atmosphere.
Flat in Evergreen Park
4.96 out of 5 average rating, 46 reviews

Newly Renovated 2 Bed Apartment

Welcome to our recently remodeled 2-bedroom apartment in Evergreen Park. Conveniently located near Advocate Christ Medical Center, restaurants and retail galore, this modern gem is a perfect retreat for travelers seeking style and accessibility. New bathroom features a rainfall shower head and Kohler finishes. Two cozy bedrooms each furnished with a queen bed. And a modern kitchen design with all new appliances.

Top guest favourite
A ranch-style home is showcased with a welcoming facade of brick and siding. Large windows provide ample natural light, while a well-maintained garden features a variety of colorful flowers. A manicured lawn and sidewalk lead to the entryway, enhancing the inviting exterior.
Home in Worth
4.94 out of 5 average rating, 113 reviews

Worth It! 3 bedroom ranch home

Relax with the whole family at this peaceful place to stay. Just minutes from walking parks, outdoor concert venue, golfing, and down town! Comfy and inviting Ranch style home offers 3 bedrooms, a fully equipped kitchen, flat screen TVs, and large windows. The private backyard has a patio, and bbq grill. A real home away from home, we look forward to your new booking.

Guest favourite
A modern living area is highlighted by a large, light-colored sectional sofa adorned with a dark throw blanket. A uniquely shaped wooden coffee table rests at the center, complemented by a textured, dark area rug. A decorative wall art piece enhances the backdrop.
Apartment in South Side
4.96 out of 5 average rating, 79 reviews

The Modern Woodlawn 2 Bed 2 Bath

Enjoy a stylish experience at this centrally-located place. Minutes from University of Chicago, the upcoming Obama Presidential Library, Golfing at the South Shore Country Club, Lake Michigan, Public Transportation and Downtown Chicago. There is an ALDI grocery store around the corner. Jewels Grocery Store is a few minutes drive by car. Free Street Parking.

Popular amenities for Oak Lawn holiday rentals

When is the best time to visit Oak Lawn?

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Frequently Asked Questions

  • How much does it cost to stay in house rentals in Oak Lawn?

    Experience the best of Oak Lawn with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Oak Lawn?

    Yes! Work meets play with ease at over 20 vacation rentals in Oak Lawn featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Where should I stay in Oak Lawn?

    Make yourself at home in Oak Lawn by choosing from our most frequently booked neighborhoods. We have over 100 vacation rentals in Worth, over 40 vacation rentals in Hometown, and over 100 vacation rentals in Chicago Ridge.

  • Are there family-friendly vacation rentals in Oak Lawn?

    Oak Lawn has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there pet-friendly vacation rentals in Oak Lawn?

    Four-legged friends are welcome in Oak Lawn. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Do house rentals in Oak Lawn have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Oak Lawn. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Oak Lawn have wifi?

    Absolutely! We offer over 10 apartment rentals with wifi in Oak Lawn. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Oak Lawn?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Oak Lawn

  • Total holiday rentals

    Explore 30 holiday rentals in Oak Lawn

  • Nightly prices starting at

    Oak Lawn holiday rentals start at €26 per night before taxes and fees

  • Verified guest reviews

    Over 1,100 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of Oak Lawn holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Oak Lawn rentals

  • 4.6 Average rating

    Oak Lawn stays receive an average rating of 4.6 out of 5 from guests

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