Should your boss be paying for your vacation?

PTO is cool. But you know what’s even cooler than getting paid while on vacation?

Getting paid while on vacation and having your boss foot the bill for all those beachside drinkies and catamaran tours, too.

The perk — AKA “PPTO,” or “paid paid time off” — is being offered by a small but growing number of companies, who are going the extra mile to not only offer paid time off but also pay for or subsidize their employees’ actual trips, per FlexJobs.

Out of office, on the house

PPTO policies, offered by companies ranging from software and healthcare startups to marketing firms, come in many forms.

• BambooHR offers an annual reimbursement stipend of $2k. The one condition: sharing photos of your OOO adventures when you eventually RTO.
• At software company FullContact, vacation stipends go up to $7k a year depending on tenure.
• Employees of live-chat platform Olark are entitled to a $1k annual vacation bonus, but only if they take at least five consecutive days off. (Twist our arm.)
• Travel companies like Expedia, TripAdvisor, and Delta Air Lines, meanwhile, are using their positions within the industry to provide free or discounted hotels, transportation, and activities.

But why…

… at a time when many companies are cutting costs and adopting “hardcore” work cultures, are some incentivizing employees to unplug for days?

Because it’s good for business — studies show that employees often return from vacation happier, more rested, and more motivated, which can also make them more productive, while paid vacations can boost employee loyalty and reduce turnover, per Inc.

• FullContact claims an 85% retention rate, which Michelle Warren, the company’s VP of human resources, told CNBC is “amazing during the Great Resignation and particularly in the tech industry.”

The issue is that people aren’t taking time off: a 2025 FlexJobs study found that nearly one in four US workers hadn’t used a single vacation day in the past year, with many deterred by “heavy workloads, manager expectations, and unsupportive company cultures.”

Policies like “paid paid” vacations encourage employees to actually GTFOOO by signaling a pro-PTO culture while also removing some of the financial burden from traveling — because the only thing better than vacay has got to be doing it on your boss’s dime.