Financial Scams to Avoid - Timeshares

Growing up, my grandparents used to treat me, my dad, and my younger brother to a week-long vacation at a lake resort about two hours from home. We made the short trek every summer, creating countless family memories. We rode horses on trail rides, spent sun soaked days fishing the lakes, took in a round or two of mini-golf, gobbled up catfish and hushpuppies at the Wednesday night fish fry, and took advantage of the indoor swimming pool every single day. My grandfather, “Peepa” to me, was an avid photographer and would capture memories on film. Some of my favorite memories were made there with my people.

The resort is nestled in a beautiful part of the state that was both convenient and fit our lifestyle… for a time.

As we got older, our busy lives made it hard to make the trip. My brother had baseball tournaments every summer that often overlapped with our trips. My dad's music business grew in the summer, making late June getaways tough. After going to college a few hundred miles away and working in the summer, it became difficult to prioritize a whole week away. While my grandparents were alive, they rarely missed a trip, but my brother, dad, and I started to miss more.

Why couldn’t you just schedule vacation for a different time of year? Because we were locked into that one specific week every year. My grandparents had a timeshare.

Back in the ‘90s, timeshare seems like a dream for vacationers: guaranteed vacations, luxury resorts, a “smart” way to save money on travel. But peel back the glossy brochures and “exclusive offers,” and you’ll find that the timeshare industry thrives on empty promises, confusing contracts, and a business model designed to drain your wallet — not protect it.

In the last 20 years, timeshares have become synonymous with nightmares, and my family had a front row seat to that progression. After my grandparents passed on, my dad inherited the timeshare… and all of its fees.

The History of Timeshares

As most things go, it wasn’t always this way. The concept of timesharing first appeared in France in the 1960s, created by a ski resort developer named Paul Doumier. He began marketing his resort in the Alps with the unique and innovative slogan, “Don’t rent a room — buy the hotel.” Buyers could purchase a share of ownership, giving them a guaranteed spot to vacation each year. The concept quickly gained traction giving middle-income families access to regular vacations without having to buy an entire second home. The model spread and took hold in the US in the 70s, beginning in Hawaii and quickly spreading throughout Florida, California, Colorado, and other vacation hot spots. As air travel became more affordable, Americans started taking advantage of timeshares more and more.

By the 1990s, big hospitality brands like Mariott, Hilton, Disney, and Wyndham had arrived on the timeshare scene, further rooting the concept and spreading the timeshare resort model throughout the country. As often happens, the entry of bigger businesses added complexity to the model in the form of new fees, confusing contracts, and fewer consumer protections.

The resale market collapsed almost entirely, making timeshares worth less than nothing. This phenomenon paved the way for a fascinating market of entire businesses centered around helping consumers escape the timeshare traps.

Here’s the truth: Timeshares are not investments. They’re a financial scam that preys on emotions and impulse decisions. Let’s explore some reasons.

1. You Don’t Own Anything Valuable

Unlike real estate, where you actually own a property that can appreciate over time, a timeshare usually gives you a right to use — not actual ownership. You’re buying access to a specific week at a property you’ll share with dozens of other people, subject to endlessly changing rules and blackout dates. Consumers often wind up paying thousands for a piece of nothing.

2. The Costs Never End

Timeshare sales pitches focus on the upfront cost — but they conveniently gloss over the perpetual expenses that come later. Every year, you’ll owe annual maintenance fees (which can easily top $1,000 or more) — and these fees can (and almost always do) increase without limit.

If the property needs repairs? You’re responsible. If the resort wants to renovate? You’re billed. Even if you’re not using it, you’re still paying.

3. Good Luck Trying to Sell It

Timeshares are notoriously difficult to sell. There’s virtually no resale market. In fact, some owners are so desperate to get rid of their timeshares that they literally give them away or pay third parties thousands of dollars just to take the burden off their hands.

Ask yourself: if this were a smart financial move, why would so many people be willing to lose money just to escape it?

4. The Sales Tactics Are High-Pressure and Manipulative

Timeshare presentations are designed to wear you down. Free gifts, “one-time offers,” and hours of psychological pressure create an environment where saying “yes” feels easier than standing your ground. Many buyers walk away signed into decades-long contracts they barely understand — without ever getting the chance to review the fine print at their own pace.

A golden rule of finance: If you have to make a decision right now, it’s probably not a good one.

5. Travel Freedom Is an Illusion

Timeshares are sold as “flexible” vacation solutions — but the reality is restrictive and frustrating. Booking the week you want (especially during school breaks or holidays) can be a nightmare. Trading weeks or locations often requires additional fees or complicated point systems that only add to the confusion and costs.

In a world where short-term rentals and hotels offer endless flexibility, locking yourself into one resort, in one network, often for decades, makes zero financial sense.

Timeshares Make You Pay Forever, Get Little, and Lose Freedom

The timeshare model is fundamentally broken — and it’s designed that way on purpose. If you’re looking for smart ways to invest your money or plan memorable vacations, skip the timeshare pitch entirely. Save your cash, stay flexible, and protect your financial freedom.

Remember: The best investments give you more options, not fewer.

After a couple of unused years, my dad eventually surrendered the timeshare our family had maintained for twenty-five years. I’ll always cherish the memories we made there with my grandparents, I’m relieved that my dad is no longer burdened with the endless costs of the timeshare.