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.

Caribbean Winter & Spring Vacations
Exclusive $100 OFF per booking

  • $200 OFF stays of 7 nights or longer
  • $150 OFF stays of 5-6 nights
  • Book by 01/15/23 for travel through 06/30/23
Aruba Divi-Divi Tree

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'.

 
 
Bahamas Snorkel

Bahamas Vacation Deals

To split a geographical hair, The Bahamas is not part of the Caribbean, as many people think. Rather, it is part of the North American plate and is bordered to the east by the Atlantic Ocean and to the west by the Gulf Stream.

 
 
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.

 
 
Jamaica Ocean Views

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.

 
 
Puerto Rico Nature Hike

Puerto Rico Vacation Deals

Puerto Rico's tropical climate and variety of land and seascapes make the island a perfect place to get active outdoors. Lovely sandy beaches and protected bays let you indulge in swimming, body surfing, and kayaking just offshore. The lush mountains are great for hiking, birdwatching and relishing the sounds of croaking frogs.

 
 
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.

 
 
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 histori capital city, Willemstad, is a stunning example of community spirit and architectural restoration.

 
 
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.

 
 
Exclusive Caribbean up to $200 OFF per Booking Offer: Valid on new bookings made 11/21/22 – 01/15/23 for travel 11/21/22 – 06/30/23. Minimum 5-night hotel accommodations at participating property and roundtrip airfare required. Minimum 7-night stay required for $200 savings. Minimum 5-night stay required for $150 savings. Savings is per booking and taken at time of booking. This entire offer is based on availability and can be modified or closed out at any time. 
Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]