I was at the desk of a small airport, the one with the vending machine that only sells overpriced water, when I pulled up a hotel booking on my phone. A five-night stay at a Rosewood. My thumb hovered over the points option, and for a second I felt that particular little thrill — no money leaving the account.
Then I did the math. And the thrill went away.
Every time I write about a luxury hotel, someone asks me the same question: can I book this on points? And for a lot of the big loyalty chains, the answer is yes. But after writing about points for a while, I’ve noticed that the question people should really be asking is different: should I?
First, the honest answer
For the major chains — IHG, Hyatt, Marriott, Hilton — you usually can. For Rosewood, the story is different. There’s no loyalty program of its own and no way to earn status there, so the only realistic way to use points is through a credit card travel portal. That’s where your points behave like cash, more or less.
So yes. Technically, you can. Here’s where it gets interesting.
The Kona Village example
Say you’re looking at a five-night stay at Kona Village, A Rosewood Resort, on the Big Island. Depending on the season, that stay can easily run $6,000 to $8,000 in cash.
Through a portal, that’s roughly 700,000 points. And a lot of people see a number like that and think they’ve found a loophole. I see something else. I see 700,000 points walking out the door.
Points aren’t free, and when you use them right, they’re worth far more than a flat 1:100 ratio against cash. Sometimes spending points genuinely hurts more than spending money would have.
Why that number matters
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 pile. For most people, it’s years of credit card spending, stacked up one transaction at a time.
Once I started thinking about it that way, I got much more selective. Because I can always earn more money. Rebuilding a big points balance takes a lot longer.
I don’t get excited about spending hundreds of thousands of points on a room. I get excited about experiences I would almost never pay cash for. Usually, that means long-haul business class.
A few years ago, we transferred points to Air France and KLM’s program — Flying Blue — and flew a family of three from San Francisco to Athens and back, in business class, for a Greece island trip. Twelve-plus hours in the air. Everyone had a lie-flat seat with a door that closes, food whenever we wanted it, lounge access, and a much easier time adjusting to a new sleep schedule.
In cash, those same tickets would have run roughly $15,000 to $21,000 for all of us.
That’s the kind of redemption that gets my attention. Would you rather get $21,000 of value from your points, or $7,000?
There’s one more thing most people miss when they book a hotel through a portal: the free nights that travel agents can sometimes unlock. You won’t see those advertised anywhere, and a points portal won’t show them to you either.
What I do instead
Rather than spending hundreds of thousands of points on hotels, I usually pay cash and book through preferred partner programs. For Rosewood properties, that means Rosewood Elite, and quite often a Rosewood Elite agent can access free nights that aren’t publicly listed.
The perks that typically come with those bookings:
- Daily breakfast for two (often a $120+ daily value)
- A $150+ property credit
- A room upgrade when available
- Early check-in when available
- Late checkout when available
- Some kind of VIP recognition
Those perks can add hundreds of dollars — sometimes thousands — to a stay, while your points balance stays intact for the flight that actually needs it.
Why luxury hotels are different
Maybe the cleanest way I know to put it: I don’t use points to avoid spending money. I use points to access experiences I would never buy with money. That’s a different mindset, and it changes what you say yes to.
When I look at a luxury hotel now, I don’t first ask what it costs in points. I ask whether that’s the best use of them. Most of the time, the answer is no.
If I want to stay at Kona Village, I can make that decision and pay for it. It’s expensive, but it’s attainable. Spending $20,000 on airfare for the whole family isn’t something I can realistically do more than once every couple of years.
Which is why flights win almost every time. Points let us experience something we otherwise wouldn’t — and that feels like the whole point of keeping them in the first place.
The Golden Hour
Before you book that splurge hotel with points, do the 60-second check: what would that same number of points get you on a long flight? If the answer is a lie-flat seat, you already know where your points belong.
FAQ
Can you actually book a Rosewood hotel with points?
Yes — through a credit card travel portal, where points act like cash. Rosewood has no loyalty program of its own, so there’s no direct points booking to speak of.
Why pay cash for a luxury hotel instead?
Cash bookings through programs like Rosewood Elite often come with breakfast, property credit, upgrades, and sometimes free nights that a points portal never shows you. Your points stay saved for flights.
What’s the best use of points, then?
For most people: long-haul business class. A redemption worth $15,000–$21,000 in cash value beats one worth $7,000 every single time.
a note from Luna
I still love the thrill of the points redemption. I just save it for the window seat now, not the hotel room. Some splurges are worth paying for in cash — and that’s perfectly okay.