Houses for Rent in Oakland, FL

Founded in 1887, Oakland stands as one of Central Florida's most well-preserved historic towns, offering a peaceful retreat just minutes from Orlando. This charming Orange County community of just over 3,500 residents features beautiful tree-lined streets and historic buildings that tell the story of its railroad town origins. The town's historic district showcases original Victorian-era architecture, while newer developments thoughtfully complement these established neighborhoods with contemporary houses and townhomes. Oakland's convenient location puts downtown Orlando within a 30-minute drive, and the West Orange Trail runs through the heart of town, offering a scenic 22-mile paved path perfect for cycling, running, or walking to Winter Garden and Apopka. Local rental options include both restored historic homes and new construction, with nearby communities showing average rental rates from $2,400 to $2,800 for three-bedroom properties. The town is home to Oakland Avenue Charter School and provides easy access to area attractions while maintaining its distinct small-town atmosphere.