The housekeeping lead
The senior member of the staff team, usually a long-tenured employee of the management company or the owner. The housekeeper sets the tone of the stay and resolves the small problems before the guest notices them. Pay the top of the regional band when the work has been visible (towels refreshed twice daily, beds remade after pool sessions, a missing item produced from nowhere). The housekeeping lead also distributes the pool of cash to the other staff. Hand them the envelope first.
The pool and garden staff
Often two people, often one. The pool service is twice-weekly in the Mediterranean and daily in the Caribbean. The gardener visits two to three times in a week. Both staff members see the property but rarely the guest. Tip into the pool, distributed by the housekeeper. Lower bound is fine unless the work was unusually visible (storm cleanup, late-night pool refresh after a party).
The houseman and the driver
Roles that vary by property. The houseman handles luggage, runs errands, and is on call for the guest. The driver shuttles the group between the villa, town, and the beach. On Caribbean properties the houseman and driver are frequently the same person, and the role merits the top of the band. On Mediterranean properties the driver is usually contracted per transfer, not staff; tip the transfer fee.
The chef
Two cases. First, the chef is independent and booked through the villa. Tip 10 to 15% of the invoice, in cash, handed directly to the chef on the final night. Second, the chef is bundled by the manager (the in-house package). Tip the chef separately from the housekeeping pool, $300 to $800 in cash, handed directly. The chef in the in-house arrangement is often the manager’s relative; the cleanest math is a direct envelope.
The villa manager
Do not tip the manager directly in the gratuity pool. The manager is paid by the property owner and the platform. If the manager has been outstanding (resolved a multi-issue arrival, recovered a missed transfer, found a chef substitute on 12 hours notice), a separate envelope of $200 to $500 with a written thank-you is the right gesture. The optics of tipping the manager from the staff pool are bad for the staff.
The platform agent
Do not tip the booking agent at Plum Guide, Onefinestay, Le Collectionist, or any other platform. Their compensation is paid by the platform on the booking commission. A written thank-you sent to the agent’s manager is the right reward for excellent platform-side work; it materially affects their year-end review and costs nothing.