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 - Save up to $200 per booking
- Book by 01/26/25 for select travel through 12/15/25
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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 -
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 -
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 -
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 histori capital city, Willemstad, is a stunning example of community spirit and architectural restoration.Curacao Republic 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 -
St. Eustacious/St. Kitts
St. Kitts and Nevis are alive with nature's bounty and vibrant wildlife. From the breathtaking National Park and Crater Lake to the magnificent coral beds, myriad species of birds and green vervet monkeys, St. Kitts engages all the senses.St. Kitts and Nevis Vacation Packages -
St. Vincent & the Grenadines Vacation Deals
Lying at the southern end of the Caribbean Sea and the Atlantic Ocean, St. Vincent offers a stunning playground far from the stresses of city life.Saint Vincent Vacation Packages
