Woodlawn Luxury Vacation Rentals

Searching for a luxury rental in or near Woodlawn? We have more than 102 luxury homes, villas, cottages, and condos that you can rent in Woodlawn.

Chicago\92s Best Vacation Rentals has a variety of luxury rentals, including vacation homes, apartments, chalets, luxury penthouses, lake homes, beachfront resorts, villas, and many luxury lifestyle options, many in Woodlawn. Whether you are traveling with families or groups, hosting a get-together, or a cocktail party, we have the perfect place for your travel plans. Our rental properties in Woodlawn are located in the top places and they come with luxury features throughout the living areas, kitchens, and bedrooms, including private pools, hot tubs, home theatres, amazing views, and plenty of space to relax.