Vacation Deals
  • Panoramic view of with ships in the bay, Ocho Rios, Jamaica
  • Woman wading through waves on Dominican Republic beach
  • Boating along clear blue waters, Bahamas
  • Sunset on Barbados Beach with palms

Caribbean Vacation Packages

If there is one word that describes the Caribbean islands, it is unhurried. Do it all or do nothing; the pace is relaxed. Miles of sun-drenched beaches and amenity-rich resorts invite you to swim, sail, dive, golf or spin the roulette wheel—the options are as diverse as the cultures. Experience Jamaica's rainforests, visit historic sites in Puerto Rico, discover Aruba's tranquil turquoise sea or revel in the Bahamas' exhilarating nightlife, duty-free shopping and gourmet dining. Discover world-class golf courses in the Dominican Republic or the spectacular half-mile peaks of the Pitons in St. Lucia. Pleasant Holidays offers the best Caribbean vacation deals suited to every taste among these idyllic islands.

Hot Deals: Caribbean
$100 OFF per booking

  • Book by 05/18/25 for travel through 12/31/25
  • Dominican Republic All-Inclusive

    Dominican Republic Vacation Deals

    The white-sand beaches, impressive mountain ranges veined with spectacular rivers and waterfalls, and saltwater lakes teeming with exotic wildlife are just part of the Dominican Republic's appeal. Whether you're looking to party, relax or explore, the Dominican Republic has a lot to offer.
    Dominican Republic Vacation Packages
    The white-sand beaches, impressive mountain ranges veined with spectacular rivers and waterfalls, and saltwater lakes teeming with exotic wildlife are just part of the Dominican Republic's appeal. Whether you're looking to party, relax or explore, the Dominican Republic has a lot to offer.
    Dominican Republic Vacation Packages
  • Jamaica Lucea Beach

    Jamaica Vacation Deals

    Undeniably unique, discover the natural beauty of Dunn's River Falls, explore the Blue Mountains or ride a bamboo raft down the Rio Grande.
    Jamaica Vacation Packages
    Undeniably unique, discover the natural beauty of Dunn's River Falls, explore the Blue Mountains or ride a bamboo raft down the Rio Grande.
    Jamaica Vacation Packages
  • Aruba

    Aruba Vacation Deals

    This speck of an island off the coast of Venezuela has guaranteed sunshine and is blessed with beaches that make you say 'ahhh'.
    Aruba Vacation Packages
    This speck of an island off the coast of Venezuela has guaranteed sunshine and is blessed with beaches that make you say 'ahhh'.
    Aruba Vacation Packages
  • Bahamas Snorkel

    Bahamas Vacation Deals

    More than 700 islands and 2,400 cays, or smaller islands, make up the gorgeous, sunswept archipelago known as The Bahamas. This idyllic getaway is favorite vacation spot for sun-worshippers and adventurers alike. Enjoy prime snorkeling and scuba diving, beautiful colonial architecture and endless views of sparkling turquoise seas.
    Bahamas Vacation Packages
    More than 700 islands and 2,400 cays, or smaller islands, make up the gorgeous, sunswept archipelago known as The Bahamas. This idyllic getaway is favorite vacation spot for sun-worshippers and adventurers alike. Enjoy prime snorkeling and scuba diving, beautiful colonial architecture and endless views of sparkling turquoise seas.
    Bahamas Vacation Packages
  • Antigua Vacations

    Antigua Vacation Deals

    Antigua's tourist office boasts that the island has 365 beaches, 'one for each day of the year'. It has great reefs and wrecks for diving and snorkelling. On neighbouring Barbuda you can track the island's fabled frigate birds and visit the Caribbean's largest rookery.
    Antigua Vacation Packages
    Antigua's tourist office boasts that the island has 365 beaches, 'one for each day of the year'. It has great reefs and wrecks for diving and snorkelling. On neighbouring Barbuda you can track the island's fabled frigate birds and visit the Caribbean's largest rookery.
    Antigua Vacation Packages
  • St. Lucia Pitons

    Saint Lucia Vacation Deals

    A spate of resort developments on St Lucia has made this high, green island one of the Caribbean's fashionable destinations, but it's still a long way from being sanitized and overdeveloped. Bananas are still bigger business than tourism in this archetypal island paradise.
    St. Lucia Vacation Packages
    A spate of resort developments on St Lucia has made this high, green island one of the Caribbean's fashionable destinations, but it's still a long way from being sanitized and overdeveloped. Bananas are still bigger business than tourism in this archetypal island paradise.
    St. Lucia Vacation Packages
  • Curacao

    Curaçao Vacation Deals

    "Choose your own adventure" perfectly describes life on Curacao. Its ruggedly beautiful landscape provides an endless bounty of fun diversions and Curacao's historic capital city, Willemstad, is a stunning example of community spirit and architectural restoration.
    Curacao Republic Vacation Packages
    "Choose your own adventure" perfectly describes life on Curacao. Its ruggedly beautiful landscape provides an endless bounty of fun diversions and Curacao's historic capital city, Willemstad, is a stunning example of community spirit and architectural restoration.
    Curacao Republic Vacation Packages
  • St. Martin

    St. Martin / St. Maarten Vacation Deals

    This lovely island is the smallest landmass on earth to be shared by two separate nations: France and the Kingdom of the Netherlands.
    St. Martin Vacation Packages
    This lovely island is the smallest landmass on earth to be shared by two separate nations: France and the Kingdom of the Netherlands.
    St. Martin Vacation Packages