Holiday rentals in Orland Park

The Adorable "Blue Breeze"!

Enjoy time at our centrally-located, family-friendly home. Close by, you'll find a public fishing dock and the popular Phil's Beach. A peaceful space with an outside patio and grill, perfect for relaxing at end of day. We also have a large driveway that can accommodate your boat making it easy to enjoy a day on Bangs Lake or a short 15 min trip to Fox Lake. Nearby attractions include the Volo Museum, Jurassic Gardens, and Lake County Discovery Museum. Please note the backyard is not fenced in.

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

Riverfront Oasis: Parks+ Kayaks+Relaxation Await!

Escape to this beautifully renovated 3-bedroom home with stunning Kankakee River views! Relax on the spacious deck or riverside patio while enjoying wildlife and peaceful scenery. Steps from Conrad Park and Island Park, you can stroll to local restaurants and shops. With all the comforts of home and just 50 miles from Chicago, it’s perfect for a getaway. Need more room? Book the cozy cabin next door tha hosts 4 more people! Your riverside retreat awaits—reserve your stay today!

Alluring Avondale Abode

Welcome to Alluring Avondale Abode, the perfect vacation rental for your next family trip or group getaway. A pet-friendly paradise, centrally located for easy travel to all the top attractions. A spacious kitchen, beautiful backyard deck, and patio create a wonderful backdrop for entertaining and relaxing. Find an array of fun games to keep all ages occupied. Book now and experience the laid-back vibe and unbeatable amenities that will make your vacation truly unforgettable.

Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home

Welcome to our historically pet-friendly home, featuring chic and updated interior furnishings. 3 bedrooms | 2 bathrooms | 2 living rooms with Smart TVs and a porch Prime Location: Just a few minutes' walk to historic Chesterton downtown Proximity: 4 miles to Indiana Dunes National Park and the beach Fully Equipped Kitchen Family-Friendly: High chair and crib available Get ready for endless adventures at the sandy shores and tree-lined trails of Indiana Dunes National Park!

2-level PH w/ 2 Luxe Suites Combined; Spa Access

The top floor sprawling ranch with duplex down offers sky & outdoors views, privacy, & cathedral ceilings, it is connected to your rear 2nd floor suite with 10ft ceilings. A burgeoning neighborhood next to the 606 Trail Amenities: - Uber-fast Wifi streaming, - Hot tub house - 80" + 75" hi-def tv's - 3 sectional couches - European decor - 2 kitchens - The popular 606 Trail access is 100 ft away, - YMCA across the street with indoor Olympic size & kiddie-pools!

Miller Beach Family Getaway!

Escape to the tranquil shores of Miller Beach with our charming Airbnb getaway. Nestled along the picturesque Indiana Dunes National Parks, our cozy retreat offers quiet views, modern amenities, and easy access to the beach with only a 4 block walk from the house. Whether you're seeking a romantic weekend for two or a fun-filled family vacation, our meticulously curated space provides the perfect home base for your family adventure!

On Walden Lake

Bring the whole family to this great place with lots of room to enjoy time with loved ones! Comforts abound from the double waterfall shower in the master bath to the beautifully updated kitchen. Windows let natural light pour into this space, and the lake views are breathtaking. A finished basement with a second kitchen and full bathroom provides plenty of room for family gatherings or co-working retreat.

Vacation home on south end of Cedar Lake

Private two story fully furnished older vacation home on the south side of cedar lake. Both bedrooms and half bath are upstairs. Main level has living room/dining room combo, kitchen and full bath. Short drive to marinas with kayak/boat rentals, public beach and boat launches. Within walking distance is a bar/restaurant with kayak rental.