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Top20 Most Popular Vacation Rental Destinations. 1 Destin, Florida; 2 Panama City Beach, Florida; 3 Ocean City, Maryland; 4 Orlando, Florida; 5 Virginia Beach, Virginia; 6 Miami Beach, Florida; 7 Key West, Florida; 8 Cape Cod, Massachusetts; 9 Galveston, Texas; 10 Outer Banks, North Carolina; 11 Maine; 12 Poconos, Pennsylvania; 13 Naples, Florida