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: Hot Deals - $150 OFF per booking

  • Book by 08/10/25 for travel through 03/31/26
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 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.

 
 
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'.

 
 
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.

 
 
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.

 
 
Hillsborough Bay, Granada

Grenada Vacation Deals

Experience the natural beauty of Grenada, from its cascading waterfalls to its meandering rivers and silky stretches of white-sand beach.

 
 
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.

 
 
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.

 
 
Saint Vincent Grenadines

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.

 
 
Turks and Caicos

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.

 
 

Caribbean $150 OFF per Booking Offer: Valid on new bookings made 06/30/2025 – 08/10/2025 for select travel 06/30/2025 – 03/31/2026. Minimum 5-night hotel accommodations at participating property and roundtrip airfare required. 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.]