Couple with santa hats on Caribbean beach

Caribbean Holiday Season Travel

With balmy weather and fantastic beaches year-round, the islands of the Caribbean are the perfect place to call home for the holidays. And with unprecedented savings and value-adds available for peak holiday season travel, you’ll find there’s no better time to plan your Caribbean getaway.
  • Aruba Our 4-Star

    This all-inclusive adults-only hotel in beautiful Palm Beach offers an inviting atmosphere and endless activity options.

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  • Paradise Island, Bahamas Our 4-Star

    Festive Season Celebrations: Christmas Tree lighting ceremony, Chanukah celebrations with Menorahs lit across the resort, and a Gingerbread Village. Reserve Thanksgiving and Christmas culinary experiences, and a New Year's Eve party.

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  • Grand Cayman Our 4.5-St

    This well-appointed resort fronts Seven Mile Beach and affords breathtaking views.
    Festive Season Celebrations: Delight in tradition and indulge in the magic of Christmas at the Westin Wonderland.

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  • Dom. Republic, Punta Cana Our 4-Star

    Festive Season Offer: Up to $600 resort credit, plus 1st child and teen stay FREE. Valid for travel through 12/31/23, with no blackout days for the holiday season.

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Riu Palace Antillas: Up to 30% OFF rates plus up to $700 resort credit valid on new bookings made by 10/31/22 for select travel 12/24/22 to 04/30/23. Discount and resort credit varies based on travel dates, length of stay and room category booked. Resort credit is not redeemable for cash, non-transferable and must be used during the length of stay.

Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]