Introduction: Why the Bills Keep Growing
Timeshares are sold as a way to “lock in your vacation costs.” The idea is simple: pay once, and enjoy guaranteed trips for life. But thousands of owners quickly realize that instead of locking in costs, their bills keep rising. Fees climb every year, surprise charges show up, and availability doesn’t match what was promised.
These issues aren’t accidental—they’re baked into the contract. Let’s look at three ways resorts use the fine print to drain your wallet.
1. Maintenance Fee Escalators
What it is: Every timeshare contract includes annual maintenance fees, but many also allow those fees to rise each year, often tied to inflation indexes or vague “reasonable increases.”
Why it matters: Because there’s usually no cap, the increases add up quickly. A $900 annual fee today can become $1,600 or more within a decade. You’re paying more each year for the same product—without any choice in the matter.
2. Special Assessments
What it is: Beyond maintenance fees, associations can levy “special assessments” for major repairs, natural disasters, or upgrades.
Why it matters: These assessments often cost thousands of dollars and must be paid on top of your regular fees. Resorts frame them as necessary upkeep, but owners rarely have any vote or control over how much is charged or how the money is used.
3. Points Availability Restrictions
What it is: Points systems were marketed as “flexible,” giving you access to multiple resorts. In reality, priority booking rules, blackout dates, and tiered status systems can make it extremely difficult to book the vacations you want.
Why it matters: Owners often find themselves paying escalating fees but unable to book the trips they were promised. To “fix” the issue, they’re pressured to buy more points or upgrade their membership—digging themselves deeper into the trap.
The Illusion of Value
What you’re really paying for isn’t guaranteed vacations—it’s a system engineered to squeeze more money out of owners year after year. And because the contract locks you in, walking away isn’t as simple as canceling a subscription.
