Orland Park holiday lettings

We found 171 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Orland Park to find one that's perfect for your trip. Holiday homes offer the amenities that you expect for your stay with friends, family or just your pet, such as Wi-Fi and a fireplace. No matter what you're looking for, you're sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Orland Park

Showing deals for:20 Mar - 27 Mar

Image gallery for Suburban Haven: Cozy Escape with a Touch of Luxury

Living area
10 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)

Suburban Haven: Cozy Escape with a Touch of Luxury

Homewood

5% off
Price is £3,320
for 7 nights, 1 home
£474 per night
includes taxes & fees
Suburban Haven: Cozy Escape with a Touch of Luxury

Find spaces that suit your style

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  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why people love visiting adventurous Orland Park

Learn about the unique charm of Orland Park with a stay in a holiday home rental. This city's hockey games, shopping and restaurants draw many visitors. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Orland Park

Are you looking for attractions to see during your stay? Venture out of your holiday home and check out everything that makes Orland Park a one-of-a-kind holiday spot. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Orland Park Sportsplex (3 mi / 4.8 km)
  • Cog Hill Golf & Country Club (5.8 mi / 9.4 km)
  • Ravisloe Country Club (10.7 mi / 17.1 km)
  • Galloping Ghost (12.9 mi / 20.8 km)
  • Oak Brook Golf Course (15 mi / 24.2 km)
  • Mistwood Golf Club (15.2 mi / 24.4 km)

Exploring the natural landscape of Orland Park

Whether you're looking for fun outdoor activities or just want to take in the scenery, Orland Park is a great place to spend some time outside. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Centennial Park (1.8 mi / 2.9 km)
  • Lake Katherine Nature Center (4.1 mi / 6.6 km)
  • Abbott Park (13.5 mi / 21.7 km)
  • Ty Warner Park (14.1 mi / 22.7 km)
  • Morton Arboretum (16.4 mi / 26.4 km)
  • Washington Park (17 mi / 27.3 km)

Transport to and around Orland Park

Fly into Chicago Midway Airport (MDW), the closest airport, located 12.4 mi (19.9 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into Chicago O'Hare International Airport (ORD), which is 24.1 mi (38.8 km) away.

If you're travelling by train, Orland Park 143rd Street Station, Orland Park 153rd Street Station and Orland Park 179th Street Station are the main stations in the city.

Frequently asked questions

What is the best area to stay in Orland Park when booking a holiday rental?
When considering a holiday rental in Orland Park, Illinois, a popular area to stay in is the downtown district. This vibrant neighbourhood boasts a variety of amenities and is particularly known for its charming atmosphere. It offers a selection of restaurants, shops, and cafés, making it a convenient base for exploring the local culture. A popular attraction nearby is the Orland Park Cultural Centre, which frequently hosts art exhibits and community events, providing visitors with a taste of the local arts scene.

Another excellent option is the area surrounding the Orland Square Mall. This lively part of Orland Park is great for those who enjoy shopping and dining experiences, as the mall features a wide array of stores and eateries. In addition to retail therapy, the nearby Centennial Park offers beautiful walking trails and a picturesque setting for outdoor activities, making it a lovely space to unwind.
How much does it cost to rent a holiday home in Orland Park?
Prices for holiday rentals in Orland Park vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Orland Park to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Orland Park holiday house rentals?
You can find great discounts on house rentals in Orland Park on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Orland Park?
In Orland Park, holiday houses and condos are the most popular types of rental accommodations, with several options available throughout the area. These properties are typically located in family-friendly neighbourhoods, providing easy access to local parks and shopping centres. Holiday houses often feature multiple bedrooms, spacious living areas, fully equipped kitchens, and private outdoor spaces, making them ideal for families or larger groups. Condos, on the other hand, usually offer a more compact living arrangement with modern amenities, including communal facilities such as pools or fitness centres.
Are there any family house rentals in Orland Park?
In Orland Park, Illinois, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. The area features spacious homes in neighbourhoods such as Southgate and the Old Orland district, where visitors can enjoy a blend of suburban charm and nearby attractions.

Many of these properties boast amenities like fully equipped kitchens for meal preparation, ample living spaces for relaxation, and often outdoor areas where children can play. Additionally, visitors can expect conveniences such as Wi-Fi and air conditioning, ensuring a comfortable stay for families.
Can I rent a holiday home with a pool or hot tub in Orland Park?
In Orland Park, there are several holiday homes available for rent that feature pools and hot tubs, making it a great choice for travellers seeking relaxation and leisure. This suburban area, located southwest of Chicago, boasts a mix of residential neighbourhoods where these properties can be found. Many rentals come equipped with private pools, hot tubs, and outdoor spaces, ideal for family gatherings or socialising with friends.
Can I find long-stay holiday rentals in Orland Park?
A long-stay holiday rental in Orland Park is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Orland Park?
In Orland Park, there are several pet-friendly house rentals available, offering a range of amenities that cater to both comfort and convenience for travellers with pets. Many of these holiday homes feature spacious backyards, allowing pets to roam freely, as well as modern kitchens and comfortable living spaces ideal for relaxation after a day of exploring the area.

The neighbourhood is well-served by nearby parks such as the Orland Park Sportsplex and Centennial Park, which provide ample opportunities for walks and outdoor activities with pets. Centennial Park, in particular, boasts walking trails, picnic areas, and scenic ponds, making it a delightful spot for both visitors and their four-legged companions.
Are there any remote work holiday rentals in Orland Park?
In Orland Park, Illinois, there are several holiday rentals that cater to remote workers, providing a suitable environment for those needing to balance work and leisure. Many of these properties come equipped with high-speed Wi-Fi, dedicated workspaces, and comfortable furnishings that make it easy to concentrate during work hours. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Orland Park holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Orland Park with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Orland Park?
In Orland Park, popular holiday rental amenities include fully equipped kitchens, which are essential for travellers who prefer to prepare their own meals. Many rentals also feature coffee makers, cookware, dishware, and utensils, allowing guests to enjoy a home-cooked experience. Additionally, dishwashers are commonly found in these properties, making post-meal clean-up straightforward.
When is the best time to visit Orland Park for a holiday rental?
July is the most popular time to visit Orland Park, Illinois, making it ideal for those seeking a vibrant atmosphere filled with summer activities. During the peak season from May to July, visitors can enjoy a variety of outdoor events and local festivals, immersing themselves in the community spirit. The warm temperatures, typically reaching the mid-20s Celsius, provide a comfortable backdrop for exploring parks, engaging in outdoor sports, or simply relaxing in one of the many local green spaces.

For families and adventure seekers, the summer months are great for picnics in the park or leisurely strolls along the scenic trails. The town's convenient proximity to Chicago also offers opportunities for day trips, allowing you to soak up the city's attractions while returning to the quieter charm of Orland Park.

If you're looking for a more budget-friendly option, October presents a wonderful alternative. During this shoulder season, the crowds thin out, and the crisp autumn air creates a picturesque setting for exploring the area's natural beauty. The vibrant fall foliage enhances the scenery, making it a great time for scenic walks and enjoying local pumpkin patches.
How early should I book a Orland Park holiday rental?
Book your Orland Park holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Orland Park home rental booking on Vrbo?
To find Orland Park holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Orland Park holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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