Compare Villas, Resorts, & Rentals in Woodlawn, Chicago, Illinois, USA
About Casai's Private Villas and Holiday Rentals in Woodlawn
Discover more than 101 vacation rentals available in Woodlawn. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Woodlawn.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Woodlawn, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Woodlawn. On average, places to stay near Woodlawn offer 559.73 ft², with nightly prices averaging US $210.
With Casai, finding and comparing holiday rentals in Woodlawn is easy and secure, often at a 30-40% discount compared to hotel prices. Simply 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 holiday rentals in Woodlawn?
- Modern Apt Near U of Chicago!
- Luxury Stay on UChicago Campus 11 min walk to hospitals
- University of Chicago Condo-Upgraded and Spacious w/Parking
- The Woodlawn Oasis is an absolutely beautiful newly rehabbed apartment!
- The Hyde Park Haven
- The Brown House - A luxurious UChicago Campus stay
- High-end 2Bdrm Garden Apt. Where Comfort Meets Style
- Luxe Loft vibe –4BR/3BA Apt– King Suite-11 minutes from downtown-Families-Groups
- Luxe Loft vibe with King Suite - 4BR 3Ba
- Cozy 3-bedroom condo near University of Chicago
How many Casai.com holiday rentals are available in Woodlawn?
As of 2025, Casai boasts over 101 properties listed in the Woodlawn area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Woodlawn.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Hyde Park Vacation Rentals in Chicago, Illinois | 110 |
