Your Next Vacation, Paid For With Points

No sooner did the Times Square Ball drop than I embarked upon my own New Year’s ritual: plotting my escape from cold, gray New York.

Would I beach-hop on the sunny shores of St. Barts? Post up within prime Instagram range of St. Lucia’s massive Pitons? Plop down at a tony resort in Turks and Caicos?

One glance at Google Hotel Search was all it took for my breezy island fantasies to collapse. Running roughly from Christmas to Easter, high season in the Caribbean and other warm-weather winter destinations means sky-high rates, especially over holiday weekends, February school vacation and spring break.

My favorite workaround: points.

Anyone who’s ever been down the rabbit hole of loyalty programs and sign-up bonuses has an opinion about points. Some people stockpile them for flights or cabin upgrades. Others aim for as many free nights as possible at plain, serviceable accommodations. As a hotel obsessive, I tend to embrace yet another strategy: splurging with points in order to stay somewhere sumptuous, even if it’s just for a few nights.

That’s how I planned our Presidents’ Day weekend getaway to Andaz Mayakoba, in eastern Mexico — a resort my husband and I already know and love, having vacationed there in late 2018 with our (then) 6-month-old son. The secluded Hyatt property, tucked on the coast between Cancún and Tulum, has a range of room types bookable using World of Hyatt points, from standard rooms (25,000 points a night) to suites (40,000 and up).

Hyatt, like several other major hotel chains, also offers a happy-medium, called Points + Cash, if you remain wary of blowing too many points at once. I tapped that option in order to book a suite, shaving $826.70 off our three-night stay without sacrificing other comforts — enough room to spread out with our toddler, and a patio to enjoy, margarita in-hand, once said toddler falls asleep at 7 p.m. And because Hyatt will roll out peak and off-peak points pricing starting in March — already in place at Marriott and Hilton — the very suite I booked will soon be even more expensive (in points) during high season.

For sunseekers as desperate as I am for a wintertime infusion of vitamin D, here are some other luxurious warm-weather getaways that you can book on points — in some cases, without spending a dollar.

Perched on Zihuatanejo’s Playa La Ropa on the Pacific Coast of Mexico, Thompson Zihuatanejo is a modern jungle retreat with rooms and villas of varying sizes, two adults-only pools (and another that’s family-friendly), two oceanfront restaurants and monthly half-moon beach parties. In February and March, standard rooms can cost up to $399 (or 25,000 points) a night.

Hyatt Ziva and the adults-only Hyatt Zilara Cap Cana are companion all-inclusive resorts that opened in late 2019 along the eastern shores of the Dominican Republic. Booking with points (25,000 a night) has considerable perks: You’ll not only get the room — around $500 a night toward the end of February — but also the food, drinks and activities, which range from cooking demos to live entertainment.

The bright, fun-spirited W Costa Rica sits on a 2,300-acre nature reserve near one of the world’s five Blue Zones, regions said to promote longevity. And although you can’t borrow a cocktail dress from Rent the Runway (a new perk at certain W hotels in the United States) you can, indeed, stand-up paddle-board and book zip-lining excursions. Rooms in February and March start around $419 (or 60,000 to 70,000 points) a night, plus a $35-a-day resort fee.

Hip stays like Condesa df are bookable on points thanks to Marriott’s majority ownership of Design Hotels, an international consortium of independent boutique hotels. The 40-room property, which lives in a 1928 building in its namesake Mexico City neighborhood, got its look from the Iranian-French designer India Mahdavi. Rooms in February and March (starting around $460) go for about 35,000 points a night.

When Hilton took over the Radisson on Aruba’s Palm Beach a few years ago, it gave the Morris Lapidus–designed resort complex — an icon of the island’s tourism scene since 1959 — a full-scale interior renovation that refreshed the lobby, guest rooms, restaurants and meeting spaces. Rooms (upward of $550 in February and March) start at 80,000 points a night; one American Express Membership Rewards point is worth two Hilton points when you transfer them online.

After being badly hit by Hurricane Irma in 2017, Hilton Key Largo re-emerged as Baker’s Cay, a 200-room Curio Collection resort on a former pineapple plantation. In addition to a secluded white-sand beach, Baker’s Cay offers eco-education workshops about the surrounding region and a Dock to Dish program that allows guests to fish for their dinner. Rooms in February and March hover around $600 (60,000 points) a night.

Opened in 2016, Kimpton’s first international resort has 266 rooms and suites, several oceanfront bungalows, a spa, three restaurants and ambitious kids’ programming. The airy architecture allows the setting — a private stretch of Grand Cayman’s Seven Mile Beach — to shine. Rates for February and March start around $699 (or 70,000 points) a night, plus a $75-a-day resort fee.

The tallest building in downtown Palm Springs, Kimpton Rowan has 153 rooms and suites, many with views of the San Jacinto Mountains. The hotel takes design cues from the area’s midcentury architecture and makes good use of its height: The rooftop has a pool, cabanas, a restaurant and bar and monthly stargazing workshops. Weekends in February and March cost around $450 to $650 (or 60,000 points) a night.

Sarah Firshein is the Tripped Up columnist for the Travel section. She formerly held staff positions at Travel + Leisure and Vox Media, and has also contributed to Condé Nast Traveler, Bloomberg, Eater and other publications. If you need advice about a best-laid travel plan that went awry, send an email to

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