A cheerfully retro waterfront motel in Islamorada with direct bay access, a dock, kayaks, and hammocks. Unpretentious and booked by repeat guests.
Why We Chose It
Drop Anchor is everything a Keys motel should be — brightly painted rooms, a dock you can fish from, hammocks swaying between the palms, and a genuine laid-back vibe that no amount of renovation could improve. Kayaks, paddleboards, and a floating dock come with the room. Walking distance to Islamorada's best restaurants.
What Stands Out
- Direct bay access and dock
- Kayaks and paddleboards included
- Hammocks and tiki huts
- Retro Keys atmosphere
- Walking distance to top Islamorada restaurants
- One of the best-value stays in the Upper Keys