3264: Does Owning a Vacation Home Make Sense? by Darrow Kirkpatrick of Can I Retire Yet on Real Estate Investing
Optimal Finance DailyAugust 29, 2025
3264
00:11:36

3264: Does Owning a Vacation Home Make Sense? by Darrow Kirkpatrick of Can I Retire Yet on Real Estate Investing

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Episode 3264:

Darrow Kirkpatrick examines the true costs and emotional implications of owning a vacation home, revealing how the dream of a getaway can quickly become a financial and lifestyle burden. By unpacking both personal experience and broader considerations, he offers a grounded perspective to help readers evaluate whether buying a second home aligns with their values and goals.

Read along with the original article(s) here: https://www.caniretireyet.com/does-owning-a-vacation-home-make-sense/

Quotes to ponder:

"Vacation homes offer convenience and familiarity, but those advantages can come with hidden costs."

"It’s easy to overlook opportunity costs when making emotional decisions, especially around real estate."

"You’ll need to honestly assess whether a vacation home supports your desired lifestyle or distracts from it."

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[00:00:51] So press play on good sleep tonight, because a good tomorrow starts with a good night's sleep. Just search for Good Sleep in your podcast app and be sure to pick the one from Optimal Living Daily. This is Optimal Finance Daily. Does Owning a Vacation Home Make Sense? By Darrow Kirkpatrick of CanIRetireYet.com

[00:01:15] It was a crisp, cloudless autumn day in 2004. My son and I set off on mountain bikes from a trailhead in rugged north Georgia. We climbed gradually on an abandoned logging road. It led up through beautiful old hardwood forests to near the summit of a stately mountain.

[00:01:35] We leveled out, then began the descent toward Lake Blue Ridge. We glided downhill on perfect trail, hugging the contours, coasting through the fall leaves. After a few minutes, we veered across the back of the mountain. Ahead, we spied an old notch in the slope, cut by heavy equipment. Arriving there shortly, we found ourselves at a cul-de-sac in a new vacation home community.

[00:02:01] A half-dozen, half-million-dollar homes were spread across the mountainside, rustic timbers, green lawns, and white driveways beckoning. The houses were furnished, but this was a ghost town. The driveways were empty. The homes were uninhabited.

[00:02:18] In my decades of mountain rambling, I ve become more and more accustomed to hiking, biking, or climbing to reach remote locations and discovering neighborhoods of sumptuous properties carved out of the wilderness. The vast majority of the time, the homes are unoccupied, empty monuments to the wealth being created in far-off cities.

[00:02:42] At first, I ll admit, I was a little jealous. There were certainly some lovely homes in some spectacular locations. At one point, stressed and bored at my regular job, I began to consider buying a vacation property of our own. I was earning enough. We could get a mortgage easily, maybe even pay cash. Perhaps a vacation home would cheer me up. A cute little place in the mountains where we could get away for weekends or longer.

[00:03:08] I spent a few days checking out properties near some of my favorite North Carolina mountain towns. Then the economic and psychological reality hit me. I was just trying to anesthetize myself to my job by throwing money and time into another project. I was looking at dropping a six-digit sum and substantial time and effort into buying and maintaining a remote property. And I would be doing that mostly so I could daydream about it while I was at work.

[00:03:38] If I was lucky, I'd spend a few weeks and a few weekends there each year. The novelty would probably wear off after a few visits. Then, the other 40 to 50 weeks of the year, I'd be paying for it. That didn't sound like the short path to true freedom and happiness. Recent statistics on vacation home ownership confirm my realization.

[00:04:01] If you buy a vacation property, there is some possibility that you can defray your expenses by renting it out occasionally. But there is little realistic hope that it'll pay for itself entirely while not burdening your finances or free time in some form. HomeAway reports that only about one half of vacation homeowners are able to cover even three quarters of their mortgage payments by renting their home. And that doesn't include management or maintenance costs.

[00:04:29] The reason that vacation homeowners struggle to cover their costs is simple. Occupancy rates are very low. Don't be fooled by statistics about occupancy rates during the season. You'll own your vacation home and pay its costs year-round. According to the footnote at HomeAway, the average owner is able to rent their home to other vacationers just 18 weeks out of the calendar year. Adding insult to injury, quote,

[00:04:58] vacation rental owners spend an average of nine hours per week marketing and managing their vacation rental properties, end quote. That's a full workday. And more than one third of those owners aren't even able to spend as much as two weeks at their own vacation home over the course of the year. A real estate expert writing at Zillow reports that the operating costs of a vacation property are like the hotel business, with expenses in the range of 60 to 75 percent of revenue.

[00:05:26] By contrast, a modest single home or apartment rental has expenses in the range of 35 to 45 percent. The detailed analysis of a vacation rental in San Diego shows a cash-on-cash return of negative 10 percent. High expenses, high workload, low fun. That's the vacation home ownership experience on average. You might do better. There are success stories.

[00:05:54] But you need to investigate very carefully because the odds are against you. For starters, to run the real numbers on a property of interest, you'll need full disclosure from the existing owner on occupancy rates and expenses. And that may be hard to get. Yet, I'll admit to the allure of owning a personal vacation property. As described, I was tempted at one low point in my career. Ultimately, we identified a more reasonable getaway solution for us.

[00:06:22] That came in the form of a small Class B RV. It has many of the positive attributes of a vacation home without some of the liabilities. The upfront and maintenance costs are decidedly lower. And importantly, an RV is mobile. We aren't stuck with taking all of our vacations in one place. In the winter or for short getaways, we'll still have our pick of beautiful vacation rental homes on the web. Yet an RV does have some vacation home liabilities.

[00:06:53] It appreciates quickly. We bought ours used. And you can't typically rent it out. There are real ongoing maintenance headaches. When I went to get ours out of winter storage this year, the tires had deteriorated, an air spring was leaking, and the windshield was cracked. Total cost? About $1,500. We own one of the smallest, cheapest RVs to operate. Even at that, due to maintenance costs and relatively low gas mileage,

[00:07:20] we have to use it carefully to ensure we actually break even on vacations. As for most real estate decisions, there's no simple rule of thumb for buying vacation properties. The odds are stacked against you financially. But ultimately, you've got to run your own numbers on renting versus owning and consult your heart. Many of the arguments for homeownership, vacation or otherwise, are more emotional than financial.

[00:07:46] There are reasons why you could choose to own a vacation home despite the costs. Pride of ownership, repeat vacations, the joy of sharing with family and friends, as a fixer-upper hobby, or to lock in an ideal retirement location for the future. Just be advised that liquidity and investment capital are more important than homeownership to a successful retirement. Many boomers are finding themselves with most of their wealth stuck in property,

[00:08:16] house furnishings, cars, and other stuff. Trying to prepare for retirement by buying still more property years in advance could be an exercise in futility. We didn't truly understand where we wanted to retire until we've been on the road exploring our options for six months after our retirement. Even now, though we love our ideal retirement location, we're happy to rent here because we don't know for sure what the future will bring.

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[00:10:34] When I read the title of this article, I immediately said no. My general philosophy is that the more you own, the more likely that stuff is to own you. However, a second home could be a lucrative investment if you see owning an income-producing asset as the primary goal and having a place to go for a vacation as a nice bonus.

[00:10:58] Short-term rentals like those found on Airbnb can be great investments, but in order to manage the risks that come with Airbnb and changing regulations, you need to find a property in a location that can also work as a long-term rental. When you're buying something that would make a great rental, whether short or long-term, you're evaluating that property financially and practically as a good fit for a rental, not necessarily your dream vacation home.

[00:11:27] So there are some trade-offs to this approach. For example, you may need to look outside typical vacation geographies. I have a few friends who own rentals in locations where traveling nurses and people on short-term assignments are prevalent, and they do very well. I actually just stayed in one of these rentals during a recent Colorado trip while my friend was in between tenants.

[00:11:52] While this small town wasn't known to be a tourist destination, we had great access to hiking and a fun community pool as well as the opportunity to explore a new area. Another bonus, we had a great vacation without paying inflated tourist prices either. And that will do it for today. Have a great day and start to your weekend. Thank you for listening. And I'll be back here reading to you tomorrow where optimal life awaits.