The Best Caribbean Hotels for a Winter Escape

Why languish in winter, when you could be beachside?
coconut drink on the beach in the caribbean

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You wake up in darkness. You leave for work in darkness. You drive home in darkness.

It’s cold. It’s always cold. Sometimes it’s cold and wet.

You need the sun. You need the warmth. You need the Caribbean.

I might be overdramatic (I’m in Scotland, where the sun rises at 9 am and sets at 3:30 pm), but the heavy weight of seasonal depression is a real thing. We need the light to operate as humans.

That’s why booking a Caribbean trip this winter isn’t just self-indulgent—it’s self-preservation. To help with your beach therapy, here are some of the best Caribbean hotels for a winter escape


Royal Caribbean Resort

royal caribbean resort
Photo: Tripadvisor

Location: San Pedro, Belize
Price: $88+
Vibe: Simple and sun-drenched
The rundown: We never said a Caribbean trip needed to break the bank. If all you’re looking for is sun, sea, and a relaxing atmosphere, Royal Caribbean Resort in Belize has you covered. Placing the splendor of the nearby reef and virgin beach at the center of everything, you’re guaranteed a laid-back and well-catered experience.

The beach cabanas are equipped with a mini kitchenette, allowing you to save even more money if needed, but there’s also a popular restaurant and beach club to grab your meals too. Two pools, an on-site diving center, and a wonderful little spa round out an excellent property. Just check the reviews—guests rave about the service and atmosphere.

Jakes Hotel

jakes hotel
Photo: Tripadvisor

Location: Treasure Beach, Jamaica 
Price: $99+
Vibe: Beachside budget brilliance
The rundown: One glance at the assortment of rooms offered at Jakes Hotel tells you the value. Secluded waterfront cabanas, Santorini-style stone villas, and open-air bathtubs are the norm here despite the price starting at just $99 a night.

The hotel started life as a restaurant and wasn’t converted until the owner gave in to requests from the hoards of customers looking for a place to sleep after eating and drinking all night. The hotel has held on to its heritage, so you’ll be glad to spend the money saved on food and drink. And it’s found on one of Jamaica’s most beautiful beaches…I guess that’s relevant.


Hyatt Regency Grand Reserve

Photo: Tripadvisor

Location: Rio Grande, Puerto Rico
Price: $290+
Vibe: Travel hackable heaven
The rundown: This beachside beauty is the perfect base for exploring Puerto Rico. It’s also the perfect base to do absolutely nothing but hang out on the beach or by the pool—whatever floats your boat. Boasting championship golf courses, a massive lagoon pool, and three restaurants, you can rest assured you’re completely covered during your time here.

Its price point is completely fair but can jump a little during the busy season—sometimes over $500. But it remains in the mid-tier section because it’s a Hyatt Category 5 hotel, meaning you can grab a standard room for just 20,000 points a night. If you were to open this card, you’d have five nights free after transferring them to Hyatt.

Barcelo Bavaro Beach

barcelo bavaro beach
Photo: Tripadvisor

Location: Punta Cana, Dominican Republic
Price: $350+
Vibe: All-hail all-inclusive
The rundown: An all-inclusive hotel can be the pinnacle of hands-off luxury travel. But it can also be the bottom of a bottomless pit of sadness, where lukewarm buffets, paint-thinner liquor, and terrible entertainment seep away at your money.

Thanfkuly, Barcelo Bavaro Beach is the former. With its stellar price point, multiple outstanding restaurants and bars, and stunning location on one of the 10 most beautiful beaches in the world, you’ve got no worries here. To top it off, it’s one of the few Blue Flag-compliant hotels in the area; your conscience can rest easy, too.


Sugar Beach, A Viceroy Resort

sugar beach viceroy
Photo: Tripadvisor

Location: Soufriere, St. Lucia
Price: $750+
Vibe: Tremendous in the tropics
The rundown: St. Lucia is as close to heaven as you’ll find anywhere on Earth. Sugar Beach, A Viceroy resort, places you at the heart of that heaven. Tucked away amongst over 100 acres of rainforest and basking in the otherworldly shadow of the island’s Piton mountains, the resort is immaculate.

Grand, spacious guestrooms spread across beach bungalows, villas, and cottages are your home base for exploring the incomparable island, while the high-end service and outstanding restaurants on sight will live long in the memory—a truly unforgettable resort.

Rock House

rock house
Photo: Tripadvisor

Location: Providenciales, Turks and Caicos 
Price: $650+
Vibe: Hard rock revelation
The rundown: Don’t mistake this for a Hard Rock Hotel. This is a far classier affair. Hidden amongst the coast-kissing rainforest and facing out to a turquoise heaven, Rock House and its array of private villas is something special.

Intimate to a fault, Rock House’s laid-back and luxurious aura is a far cry from the buzz of typical high-end resorts. Villas boast their own pools, the private strip of beach is as picture-postcard as you could ask for, and the personalized cuisine is outstanding.

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