I always book a warm-weather escape around the holidays using points from the Hilton Aspire card. It's not too late for you to do the same if you start now.

Hilton Los Cabos 1Carly Helfand

  • The Hilton Honors Aspire Card from American Express can help you earn enough points for a free winter resort vacation
  • The card offers several opportunities to rack up points quickly, including a big welcome bonus and earnings rates
  • The free weekend night certificate and resort fee credit that come with the card annually can help you add additional nights without spending
  • The Hilton Los Cabos Beach and Golf Resort, Waldorf Astoria Grand Wailea, and Conrad Maldives Rangali Island make great options for cashing in on the points you earn with the Hilton Aspire card.
  • Read more personal finance coverage.

There's no FOMO quite like the FOMO you get when you're at home in the cold over the holidays and your social media channels are awash with photos from friends and family living it up on the beach. A few years ago, I decided I would make sure I never again ended up in that position, and a warm-weather December trip became a non-negotiable calendar item.

There is, of course, one major issue with planning a tropical vacation during one of the busiest travel times of the year, and that's through-the-roof hotel prices. The key? Hotel points - enough of them to get me a yearly six-night stay in a nice beach resort. Here's how one hotel credit card - the Hilton Honors Aspire from American Express - has helped me do it year after year, and how it can help you do the same.

Keep in mind that we're focusing on the rewards and perks that make these credit cards great options, not things like interest rates and late fees, which will far outweigh the value of any points or miles. It's important to practice financial discipline when using credit cards by paying your balances in full each month, making payments on time, and only spending what you can afford to pay back.

Welcome bonus

If you don't yet have the Aspire card or you're just starting out with it, you're in luck. American Express is currently offering a welcome bonus of 150,000 Hilton Honors points after you spend $4,000 in the first three months of account opening.

It's hard to quantify exactly what 150,000 points will get you because Hilton uses dynamic pricing, which means the prices of its award stays can fluctuate. Still, you can get a pretty good idea. With one exception, Hilton award prices for a standard room top out at 95,000 points per night, so the welcome bonus alone will bring you at least a night - and most of the way to two nights - at the chain's top-tier properties.

And that doesn't mean there aren't deals to be found. You can find plenty of beachy options for 70,000 points per night or even less.

Earning Hilton points

Another star feature of the Hilton Aspire card is its sky-high earnings rate on Hilton properties. If you have any stays coming up between now and your desired winter escape and use the card to pay for them, you'll net a whopping 14 points per dollar you spend on eligible Hilton purchases.

Don't have any Hilton stays coming up? You can still earn 7 points per dollar on flights booked directly with airlines or at amextravel.com, car rentals booked directly from select car-rental companies, and purchases at US restaurants, as well as 3 points per dollar on everything else. That means that assuming you spend enough to hit the welcome bonus, you'll already have an extra 12,000 points minimum at your disposal.

Complimentary Hilton Diamond status

If you're doing the math right now and still thinking there's no way you'll generate enough points for six nights by next month, hear me out. One big perk of Hilton elite status at any level is that if you book four nights with points, you'll get the fifth night free. And because the Aspire card confers Diamond status - the highest level in Hilton's program - if you can make it to four, you're already looking at five!

There are also a slew of great benefits that come along with Diamond status, not the least of which is an enhanced earning rate for members making paid stays. So once again, if you have stays coming up between now and December and go into them with the card in hand, you'll come out earning many more points than you would otherwise.

Free weekend night

At $450 per year, the Aspire card isn't cheap. But one feature that'll help you more than offset the fee is the annual free weekend night certificate, good at almost any Hilton property in the world.

I've used my annual certificates for each of my Hilton resort stays over the years to tack a sixth night onto a fifth-night-free points stay. As long as you can find a standard award on a Friday, Saturday, or Sunday at a participating property, you're good to go.

Resort fee credit

Another major selling point for the Aspire, particularly for resort-lovers, is the $250 resort fee credit you receive annually. It's easy to use - spend $250 on eligible purchases at a Hilton resort (the chain uses that term liberally, so you have lots of options), and the money will come right back to your card, effectively bringing the annual fee down to just $200.

The good news for those who might be short on points? You can apply the credit to your room rate as long as you don't prepay. So even if you have to pay for a night on top of what you can book on points, you'll be able to lop $250 off the price.

(Even better: If you have enough points to cover your stay, you can use that credit to cover drinks at the swim-up bar.)

Referrals

Traveling with a friend, family member, or significant other? If they also get the Aspire card, you'll have twice the welcome bonus, resort fee credits and free weekend night certificates to work with.

But the icing on the cake is that if you refer said travel companion using an Amex referral link, you'll pick up an extra 20,000 points. While you're at it, if you can convince a few more friends to sign up, you can earn up to 80,000 points per year on referrals.

Where to use your Hilton points for a warm-weather vacation

Now that we've gone over how to earn the points you'll need for a last-minute resort stay, where should you use them? Here are a few of my favorite Hilton properties for beach vacations.

Hilton Los Cabos Beach & Golf Resort

If you're looking for a beautiful locale south of the border, this is it. The Hilton Los Cabos Beach & Golf Resort is a stunner with its own private, swimmable beach, which is something that's tough to find on Cabo's rocky coastline. I loved the ocean access, the infinity pool, and the food at this resort, where you can snag standard rooms for just 70,000 points per night.

Waldorf Astoria Grand Wailea 1The Waldorf Astoria Grand Wailea is another of my favorite Hilton resorts.Carly Helfand

Waldorf Astoria Grand Wailea

The largest resort on Maui, the Waldorf Astoria Grand Wailea sits on a more temperate part of the island with predictably great weather. And in addition to all the outdoor recreation activities you could want - including nine pools and a swim-up bar - you can also take art tours of the hotel to learn about its impressive collection, which includes several sculptures from famed Colombian artist Fernando Botero. Standard rooms go for 95,000 points per night.

Conrad Maldives Rangali Island

Maldives 17My upgraded villa had a private jacuzzi.Carly Helfand

Okay, if you're a US-based flyer, you probably don't want to fly all the way to the Maldives unless you've got at least six or seven nights to play with. But if you can swing it, the Conrad Maldives Rangali Island - whose lowest-priced options, the beach villas, can easily go for over $1,200 per night in December - is one place where you can get incredible value from your Hilton Honors points and free weekend night certificate.

I stayed at the property in 2018, and not only was I able to find an over-water villa at the standard rate of 95,000 points per night, but I got upgraded to a superior water villa - with a private hot-tub on the balcony - thanks to that Diamond status from the Aspire!

Click here to learn more about the Hilton Aspire card.

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Please note: While the offers mentioned above are accurate at the time of publication, they're subject to change at any time and may have changed, or may no longer be available.

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