Personal Finance

Baby Boomers Used to Love Timeshares - Here's Why They're Usually a Terrible Idea

David Beren

Published: February 7, 2025 2:29 pm

In many ways, timeshares have been hugely popular because they allow you to plan a vacation properly. As they frequently cost less than staying at hotels multiple times a year, you can travel to a timeshare and know precisely what you are getting and where. There’s no worrying over whether a hotel will be good or bad or any of the usual vacation concerns. 

It’s for these reasons that baby boomers once jumped at the opportunity to pick up timeshares all over the world. However, the cost-effectiveness of timeshares has gone from very advantageous to feeling massively overpriced. The same can be said for flexibility, which now has timeshares feeling more like a scheduling headache than anything else. 

The Golden Age of Timeshares

For an extended period, especially around the 1970s, when the timeshare exchange was introduced, this was a golden period for this vacation experience. As a way to “own” a piece of vacation rental without purchasing the entire property outright, timeshares were a fantastic way to justify traveling frequently without breaking the piggy bank every single time. 

One big reason for the rise of timeshares was the era of rising incomes as suburbs exploded and a travel boom took place. Led by post-war economic growth that lasted for decades, there was far more disposable income available to baby boomers during the 1970s and 1980s than today’s generations. 

Additionally, there was something enjoyable about knowing that you had fixed weeks out of the year to plan for a vacation in a reliable vacation home or apartment. This took a lot of the guesswork out of traveling during an age when you didn’t have websites like Trip Advisor or Expedia to give you honest reviews of hotels. 

Last but not least, owning a timeshare was once a status symbol as you could brag to your friends about this property you had a piece of in Florida or some other warm climate. 

High Initial Costs Cause A Timeshare Pause

Even with all of the advantages timeshares once had, the golden age of this ownership for baby boomers is dwindling. Among the many reasons is that baby boomers are now seeing far more of a financial crunch than they saw decades before, which means the high initial buy-in cost of a timeshare is no longer as advantageous as it once was. 

On top of this, timeshares don’t appreciate, so buying a piece of real estate you hope will grow isn’t like buying an investment property. What’s worse is that because there is a huge resale market of timeshares, you may only get half of what you originally paid if you try to sell it. It’s not impossible to imagine a scenario where one day, this wonderful timeshare you once enjoyed will sell for pennies on the dollar, according to Finn Law Group. 

What’s more important is that you might find yourself in a situation like John and Mary, who, as a retired couple, thought it would be incredible to buy a timeshare in Florida for $25,000. Instead, they are now in a situation where their original investment requires an additional maintenance fee of $1,200 per year, and they can’t find anyone to sell their share to. 

Maintenance Fees, Oh My

For baby boomers on a fixed income, the idea that ongoing maintenance fees will be a forever thing can cause real panic. There is a reasonable chance maintenance fees won’t be outrageous, but still, for individuals on a fixed income, it’s an unnecessary expense that can cut into your lifestyle. What’s worse is that fees only increase every year as they don’t go down, and they often go up faster than inflation. 

Finance Buzz says the average maintenance fee is around $1,000, besides any additional contractual considerations. Plus, you have to consider this fee is on top of any property taxes you might be responsible for, as you are likely responsible for at least a portion or share of these taxes. 

The reality is that for the amount of money you spend on fees yearly, you could likely pay for a nice hotel for a week. Yes, you’d only be staying a week compared to lengthier stay options at a timeshare, but still, the opportunity cost of these fees is abundantly clear. 

Let’s say a baby boomer couple purchased a timeshare for $20,000 as their initial upfront cost, which affords them up to two weeks each year. Over time, let’s say 10 years, this is over 140 days available for vacation. However, if the fees are an average of $1,000 per year, they have incurred an additional $10,000 in expenses to stay at a timeshare for two weeks a year. 

Limited Flexibility 

Unfortunately, because you are entering into a timeshare agreement with others, there can be limited flexibility, and you are often locked into specific weeks that may not work. Let’s say the week you are locked in is the same as a granddaughter’s theater show, and you don’t want to miss it. Unfortunately, you’re a little out of  luck. 

What’s worse is that many timeshares have a points-based system in which baby boomer owners have to compete for peak travel times, like summer or winter, which means you have unpredictable travel opportunities. 

During the golden age of timeshares, having a set week (or two) at a property wasn’t unusual. Today, with these points systems, you may even need to pay extra points during a specific week that does not work for a baby boomer schedule. The bottom line is that what should be an easy process for boomers is now more challenging than ever. 

Depreciating Value Is Very Real

One of the biggest reasons any baby boomer should stay far away from timeshares these days is how much depreciating value takes place. It’s not unheard of to see desperate timeshare owners put them up on eBay to get out of the deal and fees altogether, even at a significant loss. 

In some cases, baby boomers have sold their shares for as little as $1 on eBay to eliminate the headache. Not only are you handling this concern that you only have a limited amount of time to use the property during the year, but you also have all of these extra fees associated with maintenance and upkeep. 

The big takeaway for all baby boomers is that timeshares never gain value, regardless of what salespeople want you to believe. This is not an investment, as it will never make you money. The only takeaway is the hope for leisure time, and that’s the only actual argument. 

Impossible Resale Process

With the understanding that timeshares have a very low resale price, the more significant concern is selling any portion of a timeshare as a baby boomer with what can only be described as a near-impossible process. 

It doesn’t matter if it’s because of buyer’s remorse, not using the timeshare, or just wanting to spend money elsewhere. Any baby boomer who gets into a timeshare will find it challenging to get out. Instead of spending $25,000 on a timeshare you can’t get out of, consider how this number might be compounded in the market if you earn an average of 5%. 

In 10 years, you would have $40,722 back on your initial investment if you received a 5% return. However, any boomer locked in a timeshare they can’t get out of is likely to spend $40,000 as part of the initial timeshare cost, travel costs, and annual maintenance fees.