The Holiday Home Dilemma: Comfort, Memories and Money

 

A few days before Christmas, Jess and I baked Christmas cookies in the kitchen.

We had popped into Bredasdorp to do some shopping and the weather had turned. Grey skies, a cool breeze, the kind of day that invites you indoors rather than out. It felt like the perfect excuse to do what has quietly become our annual Christmas bake.

As we stood side by side, flour everywhere and Christmas Carols playing in the background, it struck me how familiar the moment felt.

This was something my sister, Monique, and I used to do at the same age, in this very house, with my late gran and late mom. Different generations, same kitchen, same rituals. The kind of moments that slip by unnoticed at the time, but later anchor themselves deeply in memory.

And just like that, I found myself thinking about holiday homes.

Not the spreadsheets and maintenance lists, although those matter, but the less tangible things. The memories layered into the walls. The laughter that echoes long after people leave. The quiet sense of belonging that some places give you without asking anything in return.

This home has seen my sister and I grow from 12- and 10-year-old girls into adults. It has watched our children reach and then surpass those same ages. It has held joy, chaos, grief and comfort in equal measure.

And then there is my dad.

He may no longer be out boogie boarding or fishing all day, but he loves being here. He insists on helping with the handyman jobs, even though, if we are honest, that was never his strong point ( and still isn’t!). He tries, it is appreciated, it keeps him busy and out of our hair, and somehow that feels like part of the rhythm of this place too.

Holiday homes are never just about rest.

They are also about blocked drains, temperamental appliances, the fridge that chooses the first day of your holiday to stop working, and the quiet realisation that maintenance does not take holidays. Something always needs fixing. Something always needs attention.

This is the reality. Holiday homes are lived in, worked on, loved deeply and occasionally cursed.

The Cold Financial Truth

The honest financial reality is that this house does not make sense on paper.

I rent it out from time to time, but it does not come close to washing its own face. When you factor in maintenance, insurance, rates, water, electricity and the inevitable unexpected expenses, it fails most traditional investment tests.

From a purely financial perspective, the capital tied up here could be working harder elsewhere. Generating income. Compounding. Creating flexibility.

And yet, in this season of my life, I am willing to sacrifice elsewhere to hold onto this sanctuary.

For my family.
For continuity.
For the place where I feel calm, safe and whole.

And that, too, is a conscious financial decision.

Sweating the Asset

For a holiday home to make financial sense, it needs to be rented out properly. The asset needs to be sweated.

And that is where theory and reality often collide.

In places like Arniston, demand peaks precisely when families want to be there themselves. School holidays. Long weekends. Summer. High season. We are already receiving enquiries for next Christmas.

If the goal were purely financial, the answer would be obvious. Rent it out. Often. Aggressively. Maximise yield. Let the numbers justify the capital tied up.

But doing so would fundamentally change the role this home plays in our lives.

Choosing to be here during those times means consciously forgoing income. It means accepting that the house will never fully wash its own face. It means understanding that, financially, this is not an optimised decision.

Wrongly or rightly, it is a trade off I make with my eyes wide open.

Legacy Is Not Always Logical

This house was my late mom’s pride and joy.

She poured herself into creating a space that welcomed everyone. A place that felt warm, familiar and grounding. If the walls could talk, I am sure they would quietly giggle continuously, having witnessed decades of stories unfold within them.

Legacy is often spoken about in financial terms. Assets passed down. Value preserved. Wealth transferred.

But legacy also lives in kitchens where generations bake together. In rooms where children grow up and then return as adults. In places that hold grief gently and joy loudly.

Not all legacy fits neatly into a spreadsheet.

When Letting Go Is the Right Choice

In a couple of days, my ‘other‘ parents are arriving to visit.

These are people who have been part of my life for as long as I can remember. We grew up together. Our families holidayed together. Our parents were friends long before we understood what that meant.

They had their own holiday home for many years, from when their children were small. It was filled with the same kinds of memories. Chaos, laughter, long meals and familiar rituals.

Two years ago, they made the incredibly tough decision to sell it. It was the right decision for their family. Life had shifted. Children were grown. In laws, other holiday homes and a daughter now living abroad meant the house no longer served them in the same way.

And yet, even now, they miss it with their whole beings.

Their decision was different to mine. And it was no less valid.

This is the quiet truth about holiday homes. There is no universally right answer. Only what serves a family in the season they are in.

The Question That Matters

The real question is not whether owning a holiday home is a good investment.

The real question is whether it still serves the life you are living now.

Sometimes holding on is the right choice.
Sometimes letting go is an act of wisdom.
And sometimes the financially correct decision still carries emotional cost.

That does not make it wrong.

Closing Reflection

For me, this house remains a place of refuge. A place where memories are still being made. A place where my family gathers, where time slows and where I feel anchored.

I know the cost. I understand the trade offs. And for now, I choose it anyway.

Wealth is not only about optimisation. It is about intention. About making decisions with clarity and honesty, allowing room for what makes us feel human.

Sometimes, the most valuable assets are the ones that never show up neatly on a balance sheet.

And that is ok.