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Clock tower pavilion and brick plaza on Plant Street in downtown Winter Garden

Orlando & Kissimmee · 28 licensed rentals

Winter Garden & Windermere vacation rentals

Photo: Freeholdman12 · CC BY 4.0

Winter Garden grew up around citrus and the railroad, and its historic downtown on Plant Street is one of the most walkable small-town main streets in the Orlando area. The West Orange Trail runs right through the middle of it, with cyclists rolling past the cafes, the restored Garden Theatre and the Saturday farmers market. Just south, Windermere is a small lakeside town on the Butler Chain of Lakes, a string of clear, connected lakes known for boating and water-skiing.

Rentals here are pool homes in the newer neighborhoods around SR 429 and lakefront houses near Windermere, a calmer base for guests who want quiet evenings and a real town to come back to. SR 429 makes the drive to Walt Disney World quick, and Dr. Phillips and its Sand Lake Road restaurants are a short hop east.

Things to do near your rental

  • Plant Street shops, restaurants and the Garden Theatre
  • West Orange Trail for biking and walking
  • Boating on the Butler Chain of Lakes
  • Lake Apopka Wildlife Drive north of Winter Garden

Licensed by the state of Florida

28 Winter Garden vacation rentals

Every listing starts from an active state license. Owners who claim their listing add photos, rates and a direct booking link, and appear first.

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