The minimum practical package is commercial general liability specifically endorsed for short-term rentals, a meaningful umbrella policy, business personal property and business-income coverage, and workers’ compensation if staff are employed. Add marine, golf-cart, auto, cyber, liquor, E&O, crime, and employment-practices coverage when the operator provides or controls those activities.
The policy must cover transient guest use and should name the HOA and its relevant management parties as additional insureds. Insurance supplements—rather than replaces—the operator’s contractual duty to defend, indemnify, and hold the HOA harmless for short-term-rental liabilities.