Compare Vacation Rentals & Rent By Owner Homes in Kenwood, Chicago, Illinois, USA
About Kenwood Vacation Rentals
With more than 655 Kenwood 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 Kenwood.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Kenwood, 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 Kenwood. Places to stay near Kenwood are 660.17 ft² on average, with prices averaging US $362 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Kenwood 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 Kenwood, IL
Frequently Asked Questions About Kenwood?
What are the top vacation rentals in Kenwood?
- 1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier
- 4 #1S - 4 Bedroom/1.5 Bath Condo near McCormick Place, Wintrust Arena
- Penthouse, Lux stay near Downtown, McComick & Lake
- Gorgeous historic mansion on UChicago campus. Renovation with original detail.
- Large historic home minutes from downtown Chicago and the lakefront.
- Gather, relax, enjoy— in chic luxury home near Lake Michigan & McCormick Center
- 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
How many Rentbyowner vacation rentals are available in Kenwood?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 655 in the Kenwood 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 Kenwood.
Nearby Neighborhood (3)
| Neighborhood | Property Count |
|---|---|
| East Hyde Park Vacation Rentals in Chicago, Illinois | 31 |
| Indian Village Vacation Rentals in Chicago, Illinois | 550 |
| North Kenwood Vacation Rentals in Chicago, Illinois | 660 |
