A couple places were mentioned where some of it was filmed.
1) Cypress Gardens - what scene was that??
2) Winter Haven - What scene was that.
Winter Haven is close to Cypress Gardens but was not much in 1959 pre-Disney time.
I only saw this once so I may have missed it.
Probably the scene where Tony takes his beatnik girlfriend on a picnic - my guess for filming that scene would have been Key Biscayne, because at that time it was mostly undeveloped...
South Beach Florida
shareFilming locations for
A Hole in the Head (1959)
Cardozo Hotel - 1300 Ocean Drive, South Beach, Miami Beach, Florida, USA
(hotel)
Collins Avenue, South Beach, Miami Beach, Florida, USA
Cypress Gardens - 2600 S. Lake Summit Drive, Winter Haven, Florida, USA
Miami Beach, Florida, USA
Miami, Florida, USA
Samuel Goldwyn Studios - 7200 Santa Monica Boulevard, West Hollywood, California, USA
(studio)
South Beach, Miami Beach, Florida, USA
Winter Haven, Florida, USA
You can't go wrong drowning politicians Henry. The Black Swan (1942)