What makes a thing cool? Is it designed to be cool — like an iPhone or a viral TikTok video? Is it born that way, like we imagine David Bowie was? Is coolness bestowed by someone influential, maybe one named Kardashian? Whatever the origin, most people would say that the timeshare train left the “cool” station years ago. And that’s not really fair, is it? The resorts are stunning and well located, and most are offered by world-class brands like Marriott, Disney, and Hilton. They provide many owners with an enviable lifestyle. And when compared to Airbnb, timeshare vacations provide a sense of certainty and comfort when traveling. These days, it doesn’t get much cooler than that.

So why the bad rap? I want to talk about the industry’s perfidious reputation and bust a few myths. But mostly I want to explain why I feel timeshare resorts are actually really cool.

3 MYTHS About The Timeshare Industry

• MYTH: Timeshares are only located near beaches or Orlando.
  • FACT: Timeshares are increasingly being developed in urban areas like New York, Austin, and San Francisco, as well as international destinations like Thailand, Bali, and Spain.

• MYTH: Timeshares are boring.
  • FACT: Timeshares are a blast: multiple pools and lazy rivers, restaurants, and bars on-site, and enough space to entertain guests in your room, plus amenities like spas, fitness centers, kids programs, and more. Fun is built into the formula.

• MYTH: In terms of design, timeshares have a “cookie-cutter” look.
  • FACT: The new generation of timeshare resorts have designs that are unique, locally influenced, and stunningly beautiful. Just take a look at the new La Pacifica Los Cabos by Hilton Grand Vacations in Baja California — it’s a show-stopper.

• MYTH: Timeshares are rigid and lock you into predetermined selections.
  • FACT: Timeshares are becoming more and more flexible, thanks to points-based systems and third-party partners, and owners are taking full advantage. The savvier among them are using owner rentals as a way to add even more flexibility and optionality.

Timeshare Industry has Value

One of the biggest contributors to timeshare’s cool factor, in my opinion, is its value. Not the tangible value of property co-ownership, which is what timeshare technically is but, as we know, typically has very little value as a real estate investment. I’m talking about the intangible value created by the recurring time-annuity of ownership — the ability to travel every year at a higher quality or for less money than one would typically spend on similar accommodations over a period of time. Timeshare owners consistently say that they travel considerably more and at higher echelons than they would have without it. That commitment to travel — and the memories it creates — pays off in dividends.

Putting the warm and fuzzy stuff aside for a moment, it’s the resorts themselves I want to focus on. Why? When booking vacations, most travelers are forced to choose between two flawed options: a hotel room and a vacation rental. Hotels are cramped, expensive, and inconvenient for groups or families. Vacation rentals are rarely professionally cleaned or managed (like, whose house is this anyway?). They can be inconsistent at best, unsafe at worst. (And as more travelers come to that realization, Airbnb seems less and less like the cool new kid on the block.) Timeshare resorts combine the space and features of a home rental with resort-like services and amenities — a very cool way to vacation. On several occasions, I’ve had the pleasure of converting a skeptic into a timeshare lover by simply booking one and taking them. Their reactions are always the same: “This is a timeshare?” Yes, this is a timeshare.

Respect the Timeshare Industry

Despite that, timeshare resorts still don’t get the respect they deserve. Most people who don’t know the industry think two things when you say the word timeshare: 1. Do those still exist? 2. Scam. (Not necessarily in that order!) I don’t say this to be pejorative — I’ve done the research and it’s true. I still feel it’s somewhat unfair. The industry leaders are building better products than ever and have taken major steps to mitigate the bad behavior synonymous with the timeshare presentations of yesteryear. But the perception issues still curtail growth, particularly amongst younger generations.

The unscrupulous behavior of the past still resonates in memes and sitcom episodes about timeshare presentations. That reputation overshadows a lot of the progress today’s big brands have made in tightening the industry up — not to mention the magnitude of the incredible resorts being built today. This has a flywheel effect: The bad (and often erroneous) reputation damages the trust of a potential customer, which diminishes natural demand, which requires more aggressive (or at least intense) sales and marketing tactics to maintain sales. Until demand is created naturally (i.e. people want timeshare like they want a new Tesla — or anything a Kardashian touches) and not manufactured during a sales presentation, this cycle will likely persist. And to be clear, people should want it! Because life is short and vacations make people happy — and investing time and resources* in something that makes you happy will make you happy.

Timeshare Industry Moving Forward

While some forward-thinking timeshare companies are already moving in the right direction, there is no doubt they will need to address these issues head-on before the perception and the product can begin to fully align. Younger generations are more empowered and knowledgeable as consumers and thus, less likely to be susceptible to information asymmetry.

So it’s clear that timeshare resorts are cool (if you’re not convinced of this yet, then shame on me). But many of the contracts are still too rigid or difficult to divest from — especially for millennials who favor experiences over possessions. That’s why I’m excited and curious to see what the future holds for the industry. The good news is that younger people are also traveling more frequently and farther from home — especially after the pandemic. So, if timeshare companies are paying attention (they are), there is a massive wave to catch and some very cool resorts to show off.

Read Yes, Timeshares are Actually Cool on Resort Trades