The 114-room Cheeca Lodge was one of the original luxury properties on Islamorada, dating to 1946 and earning plenty of celebrity cachet over the years (high-profile guests have included George W. Bush). The property was rebuilt after a fire gutted its main building in 2009, and now has bright, spacious rooms with tropical-luxe decor and massive bathrooms. The lush grounds are especially pretty at night, with Tiki-torch-lit paths. But the hotel's beach is manmade -- there's even a rock ledge on the water's edge -- making it muddy at times and less than ideal for swimmers and waders. And the family pool can get crowded; those traveling without children will probably prefer the much calmer adult-only pool.