Every time I post a luxury hotel, someone inevitably asks the same question:

“Can I book this on points?”

Sometimes for IHG, Hyatt, Marriott, and Hilton, the answer is yes.

The better question, though, is whether you should.

One thing I’ve noticed after years of collecting points is that many people become so focused on avoiding cash that they stop thinking about value altogether. If a hotel stay costs 700,000 points instead of $7,000, it feels like a win because no money is leaving your bank account.

But points aren’t free. They have value well beyond a 1:100 ratio when used right.

And sometimes spending points is actually more painful than spending cash. Let me explain:

The Kona Village Example

Let’s say you’re looking at a five-night stay at Kona Village, A Rosewood Resort.

Depending on the season, that stay could easily cost $6,000-$8,000.

Since Rosewood doesn’t have a loyalty program and there’s no way to get status, the only realistic way to use points is through a credit card travel portal, where points essentially act as cash.

Many people see that and think they’ve found a loophole.

I see something different.

I see 700,000 points disappearing.

Why That Number Matters, and What We Save Our Points For

Whenever I look at a redemption, I ask myself what I had to do to earn those points. Seven hundred thousand transferable points is not a small amount.

For many families, that’s years of credit card spending. Once I started thinking about points that way, I became much more selective about how I used them. Because while I can always earn more money, rebuilding a massive points balance takes time.

Personally, I don’t get excited about redeeming hundreds of thousands of points for a hotel room. I get excited about experiences I would almost never pay cash for.

For our family, that usually means long-haul business class flights – here’s how I find and book them.

A few years ago, we used transferred points to fly to Flying Blue in business class as a family of three from San Francisco to Athens and back for a Greece island hopping trip. The flight was more than 12 hours long, and everyone had a lie-flat seat with a closing door, food whenever we wanted it, lounge access, and a MUCH easier time adjusting to sleep schedules.

Had we paid cash, the flights would have cost roughly $15,000-$21,000 total.

That’s the kind of redemption that gets my attention, because wouldn’t you rather get $21k of value vs. just $7000?

Plus, there’s another caveat you’re not considering when booking through points portals – the free nights you could get that are only available through travel agents.

What We Do Instead

Rather than spending hundreds of thousands of points on hotels, we typically pay cash and book through preferred partner programs. For Rosewood properties, that means Rosewood Elite, and quite often, Rosewood Elite agents have access to free nights that aren’t always publicly available.

Benefits typically include:

• Daily breakfast for two (often $120+ daily value)
• $150+ property credit
• ⬆️ Room upgrade when available
• ⏰ Early check-in when available
• Late checkout when available
• ⭐ VIP recognition

In many cases, those perks can add hundreds to thousands of dollars of value to a stay while allowing us to preserve our points balance for flights, while also giving us access to free nights.

Why Luxury Hotels Are Different

Maybe the simplest way to explain it is this:

I don’t use points to avoid spending money, I use points to access experiences I would never buy with money, which is a completely different mindset.

When I look at a luxury hotel, I don’t immediately ask how many points it costs, I ask whether that’s the best use of those points.

Most of the time, the answer is no.

Which is why you’ll usually find us transferring our points to airlines and paying cash for hotels instead.

If I want to stay at Kona Village, I can make that decision and pay for it. It’s expensive, but it’s attainable, but spending $20,000 on airfare for my family isn’t something I realistically do more than once every couple of years.

That’s why flights win almost every time. Points allow us to experience something we otherwise wouldn’t.

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