Compare Vacation Rentals & Rent By Owner Homes in Woodlawn, Chicago, Illinois, USA
About Woodlawn Vacation Rentals
With more than 635 Woodlawn vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Woodlawn.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Woodlawn, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Woodlawn. Places to stay near Woodlawn are 702.51 ft² on average, with prices averaging US $371 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Woodlawn with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Other Places to Stay in Woodlawn, IL
Frequently Asked Questions About Woodlawn?
What are the top vacation rentals in Woodlawn?
- 1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier
- Penthouse, Lux stay near Downtown, McComick & Lake
- Gorgeous historic mansion on UChicago campus. Renovation with original detail.
- Luxury Stay on UChicago Campus 11 min walk to hospitals
- Modern Apt Near U of Chicago!
- 1 Mi to University of Chicago: Urban Escape!
- University of Chicago Condo-Upgraded and Spacious w/Parking
- Beautiful, modern 3 bed 2 bath condo near Hyde Park, Obama Center and Lakefront
- The Woodlawn Oasis is an absolutely beautiful newly rehabbed apartment!
- The Hyde Park Haven
How many Rentbyowner vacation rentals are available in Woodlawn?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 635 in the Woodlawn area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Woodlawn.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Hyde Park Vacation Rentals in Chicago, Illinois | 62 |
