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Orland Park, IL vacation rentals
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Best Vacation rentals and Airbnb offers in Orland Park, IL

Compare Vacation Rentals for Families in Orland Park, IL

Make family travel to Orland Park, IL seamless with spacious vacation rentals located just minutes from top city attractions.

Best View And Luxury Style, Located In Downtown - Orland Park, IL
Orland Park, IL
06/27 – 07/04
$577/nighttotal: $4039 (7 )

Best View And Luxury Style, Located In Downtown

1 2
apartment , Oak Lawn
This Oak Lawn apartment rental boasts stunning panoramic views of Wacker Drive, Lake Michigan, Navy Pier, the Chicago River, and Trump Tower, offering convenient access to downtown Chicago attractions.
The one-bedroom, one-bathroom unit sleeps two guests and features a king-sized bed, fully equipped kitchen, high-speed Wi-Fi, large TV, and access to a swimming pool, jacuzzi, fitness center, and sauna.
3br/2ba + Pull Out Sofa Bed + No Stairs + Backyard - Orland Park, IL
10 43 reviews
Orland Park, IL
06/27 – 07/04
$406/nighttotal: $2842 (7 )

3br/2ba + Pull Out Sofa Bed + No Stairs + Backyard

1 2
apartment , Worth
This stylish 3-bedroom vacation rental is located in Worth, just a short distance from the city's main attractions, such as the Worth Museum and the Worth Riverwalk. The home features a fully equipped kitchen, a spacious living area, two bathrooms, a private garden, and parking for up to two vehicles, perfect for a family vacation or a group getaway.
Grade A Working Class Safe Neighborhood 3br Up To 6 Guests. Updated & Best Price - Orland Park, IL
10 3 reviews
Orland Park, IL
08/10 – 09/09
$216/nighttotal: $6480 (30 )

Grade A Working Class Safe Neighborhood 3br Up To 6 Guests. Updated & Best Price

3 2
apartment , Burbank
This Burbank vacation rental is conveniently located near Chicago Midway International Airport, a 25-minute drive from downtown Chicago, offering easy access to parks like Cook County Forest Preserves and attractions such as the Museum of Science and Industry and Art Institute.
This three-bedroom, one-bathroom home sleeps six guests comfortably, featuring a full kitchen with dishwasher, washer/dryer, smart TV, free Wi-Fi, ample parking, and enhanced security with three Ring cameras.
Matteson Fhs Rental - Orland Park, IL
Orland Park, IL
06/27 – 07/04
$687/nighttotal: $4809 (7 )

Matteson Fhs Rental

1 2
apartment , Matteson
**Matteson Apartment**
This apartment is perfect for families or groups visiting Matteson. It is located in a quiet neighborhood, just a short walk from the city center. The apartment has two bedrooms, two bathrooms, and can accommodate up to 12 guests. It is fully equipped with a kitchen, air conditioning, and a garden. Guests can also enjoy free Wi-Fi and parking.
The apartment is also pet-friendly, so you can bring your furry friends along on your vacation. The garden is perfect for relaxing or playing with the kids. And the free parking is a great convenience, especially if you are renting a car.

Best Orland Park, IL vacation rentals with parking

71 M² House ∙ 4 Bedrooms ∙ 10 Guests - Orland Park, IL
Orland Park, IL
08/10 – 09/09
$424/nighttotal: $12720 (30 )

71 M² House ∙ 4 Bedrooms ∙ 10 Guests

4 2
house , Richton Park
Vacation house to rent for up to 10 people. Your accommodation will be located in Richton Park.
Facilities and services: a freeze, a kitchen and a dish washer.
Serenity 3bd Home Free Parking&wine Oversized Yard - Orland Park, IL
Orland Park, IL
07/02 – 07/05
$418/nighttotal: $1254 (3 )

Serenity 3bd Home Free Parking&wine Oversized Yard

2 6
house , Burbank
This house in Burbank offers 2 bedrooms and 1 bathroom, with complimentary WiFi and on-site parking, situated approximately 3.1 miles from Midway International Airport and 10-13 miles from Chicago attractions including Guaranteed Rate Field and the United Center.
This accommodation accommodates up to 13 guests and features a fully equipped kitchen, an oversized yard, and is a non-smoking property managed by a private host.
Beautiful Suburban Home 30 Minutes From Downtown Chicago! - Orland Park, IL
9.2 5 reviews
Orland Park, IL
07/02 – 07/05
$468/nighttotal: $1404 (3 )

Beautiful Suburban Home 30 Minutes From Downtown Chicago!

3 6
apartment , Richton Park
This Richton Park home, near Winnebago Dog Park (1.5 miles) and Hanger Clinic (2.7 miles), offers convenient access to Richton Park Station (a 12-minute walk).
The three-bedroom, two-bathroom house sleeps up to 10 guests and features a fully equipped kitchen with appliances including a dishwasher, a Smart TV, and on-site parking; nearby attractions include Franciscan St. James Health - Olympia Fields and WellGroup HealthPartners (within 6 miles).
150 M² House ∙ 4 Bedrooms ∙ 8 Guests - Orland Park, IL
Orland Park, IL
08/10 – 09/09
$606/nighttotal: $18180 (30 )

150 M² House ∙ 4 Bedrooms ∙ 8 Guests

4 2
house , Tinley Park
House listing for 8 guests. You will be based in Tinley Park.
Services and facilities include a washing machine, a fridge and air conditioning. Enjoy free parking with this accommodation in Tinley Park!

Frequently Asked Questions about vacation rentals in Orland Park, IL

  • What are the top family-friendly attractions in Orland Park, IL?

    The Orland Park Recreation Center offers a wide range of activities for kids, including swimming, sports, and arts and crafts. The Centennial Park is a great place for a picnic or a family walk, and it also has a playground and a splash pad. The Orland Park Public Library also hosts many family-friendly events throughout the year.
  • What are the best Airbnb and vacation rentals in Orland Park, IL?

    Luxurious Townhome, Orland -Huntington Rental and Orland Park -Huntington Ct are the most popular Airbnb and vacation rentals in Orland Park, IL among travelers.

  • When is the best time to book a vacation rental in Orland Park, IL?

    The best time to book a vacation rental in Orland Park is during the shoulder seasons, in the spring or fall. You'll avoid the crowds and the higher prices of the summer months, but you'll still enjoy pleasant weather. The summer months are popular for families with kids, and the fall is a great time to see the changing leaves.
  • What are the most popular Airbnbs in Orland Park, IL?

    Among the Airbnbs in Orland Park, IL, Luxurious Townhome, Orland Park- Huntington Rental and Lovely 3 Bedroom Town House Fully Furnished/wi-fi are the most popular ones.

  • What events or festivals should visitors check out in and around Orland Park, IL?

    The Orland Park Village Center hosts a variety of events throughout the year, including the Orland Park Summerfest and the Orland Park Holiday Festival. The nearby city of Tinley Park has the popular Route 66 Ribfest in June, and the Chicagoland Speedway hosts NASCAR events throughout the year.
  • What are the best vacation rentals with a pool in Orland Park, IL?

    Luxury 1 Bedroom Near Orlandsquare Mall, Lovely - Spacious 2 Bedroom Unit and Orland Park Oasis are the best vacation rentals with a pool in Orland Park, IL.

  • What are the best budget-friendly activities in Orland Park, IL?

    The Orland Park Public Library offers free programs and events for all ages, including book clubs, movie nights, and craft classes. The Centennial Park is a great place for a free picnic or walk, and it also has a playground and a splash pad. The Orland Park Village Center has a variety of free events throughout the year, like concerts and farmers markets.
  • What are the best rentals for families and kids in Orland Park, IL?

    The best rentals for families and kids in Orland Park, IL are Orland -Huntington Rental, Orland Park -Huntington Ct and Orland Park- Huntington Rental.

  • What are the best restaurants with local dishes in Orland Park, IL?

    Orland Park has a variety of restaurants serving local dishes, but you'll find a great selection of Chicago-style pizza. Some local favorites include Lou Malnati's Pizzeria, Gino's East, and Pizzeria Bebu. For a more casual experience, try the Orland Square Mall food court, with its variety of options.
  • What are the best rentals or Airbnbs with a jacuzzi in Orland Park, IL?

    The best vacation rental or Airbnb with a jacuzzi in Orland Park, IL is Luxury 1 Bedroom Near Orlandsquare Mall.

  • What are the best walking or cycling routes in Orland Park, IL?

    The Centennial Park has a paved walking and biking path that circles the park. You can also enjoy a scenic walk or bike ride along the Des Plaines River Trail, which runs through Orland Park. The Orland Park Village Center is a great place to start a walk or bike ride, with its many shops and restaurants.
  • Are there pet-friendly attractions in Orland Park, IL?

    Centennial Park is a great option for pet owners, with its large open space, paved walking paths, and dog park. Many restaurants in the Orland Park Village Center have outdoor patios that are pet-friendly.
  • What are the benefits of choosing a vacation rental in Orland Park, IL?

    Vacation rentals offer more space and privacy than hotels, making them a great option for families or groups. They often come with kitchens, allowing you to save money on dining out. You can also find rentals with amenities like pools, hot tubs, and fireplaces, which can enhance your stay.

Destinations nearby

Choose the Right Vacation Rentals with a Terrace in Orland Park, IL

Enjoy a Orland Park, IL vacation rental with a balcony and stunning city skyline views for a truly memorable stay.

Comfortable And Cozy 4br 2ba Home In Worth - Orland Park, IL
Orland Park, IL
07/02 – 07/05
$408/nighttotal: $1224 (3 )

Comfortable And Cozy 4br 2ba Home In Worth

1 6
apartment , Worth
This 4-bedroom, 2-bathroom house in Worth, IL offers a spacious retreat with newly installed flooring and central air conditioning, perfect for families and groups seeking a comfortable stay. Located in a tranquil suburban community, it provides easy access to local amenities and is a short drive from Chicago's attractions.
This single-family home accommodates up to 8 guests and features generously sized bedrooms with ample closet space, making it ideal for long-term stays. Pets are welcome, and the property includes internet and a kitchen for your convenience.

Best Orland Park, IL vacation rentals with air conditioning

120 M² House ∙ 3 Bedrooms ∙ 6 Guests - Orland Park, IL
Orland Park, IL
08/10 – 09/09
$602/nighttotal: $18060 (30 )

120 M² House ∙ 3 Bedrooms ∙ 6 Guests

3 2
house , Tinley Park
Accommodation for 6 guests. You will be in Tinley Park.
Services and facilities: a washing machine, a kitchen and air conditioning.
Soothing 3-bedroom House With Ac In Richton Park - Orland Park, IL
8.0 2 reviews
Orland Park, IL
07/02 – 07/05
$346/nighttotal: $1038 (3 )

Soothing 3-bedroom House With Ac In Richton Park

3 6
apartment , Richton Park
This 3-bedroom, 1-bathroom vacation home in Richton Park is conveniently located near Odyssey Fun World and Orland Square, with Space Golf and Centennial Park Aquatic Center also a short drive away. This residence accommodates up to 6 guests and features a jetted bathtub, air conditioning, and heating for year-round comfort.
* Extended Stay* Matteson Fhs Rental - Orland Park, IL
Orland Park, IL
07/02 – 07/05
$749/nighttotal: $2247 (3 )

* Extended Stay* Matteson Fhs Rental

1 6
apartment , Matteson
This pet-friendly apartment in Matteson is the perfect choice for families and groups of up to 12 guests. The apartment features 2 bathrooms, a garden, air conditioning, and free parking.
The apartment is fully equipped with a kitchen with a fridge, microwave oven, and dishwasher, as well as internet access. Guests can also enjoy the garden and air conditioning.
Large Mcm Hideaway In The Forest - Orland Park, IL
Orland Park, IL
08/10 – 09/09
$270/nighttotal: $8100 (30 )

Large Mcm Hideaway In The Forest

1 2
apartment , Palos Park
This Palos Park mid-century modern home, situated on 1.25 acres near Swallow Cliff Forest Preserve and its trails, offers easy access to both nature and downtown Chicago (20 miles away).
This four-bedroom, three-bathroom house features a chef's kitchen, fireplaces, a finished basement, and accommodates up to 10 guests, perfect for families or groups enjoying biking, horseback riding, or exploring nearby attractions.
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