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.
Caribbean Vacations
Up to $200 OFF per booking
Up to $200 OFF per booking
- Book by 01/18/26 for select travel through 08/31/26
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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 -
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 -
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 -
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 -
Barbados Vacation Deals
All the comforts of home are close at hand as Barbados is one of the most developed islands in the region. Most famous for its endless pink-sand beaches, this charming tropical island offers a peaceful mix of classic calypso rhythms, an island-time vibe and world-famous rums.Barbados Vacation Packages -
Bermuda Vacation Deals
Think Bermuda and images of tidy pastel cottages, pink-sand beaches, and quintessential British traditions like cricket matches and afternoon tea spring to mind. Here, challenging golf courses, 75 miles of pristine coastline, an incredible coral reef, underground caverns, nature reserves and historic Hamilton invite endless exploration.Bermuda Vacation Packages -
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.Curaçao Vacation Packages -
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 -
Turks & Caicos Vacation Deals
Fringed with exquisite beaches and several hundred miles of coral reef, the Turks & Caicos Islands consistently rank on the world's top 10 dive lists.Turks & Caicos Vacation Packages