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.

Fall & Winter Sale
EXCLUSIVE $100 OFF per booking

  • For new bookings made by 04/19/20
  • For travel through 12/20/20
All Deals Include: Round-trip flights, hotel accommodations, taxes and more
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.

 
 
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.

 
 
Turks and Caicos

Turks & Caicos Vacation Deals

At first glance these oddly named and misshapen islands may not appear to be the prettiest in the Caribbean, covered as they are with cactus and thorny acacia trees. They are, however, fringed with exquisite beaches and several hundred miles of coral reef that keeps the Turks & Caicos on the world's top 10 dive list.

 
 
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.

 
 
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'.

 
 
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.

 
 
Crane Beach, Barbados, Caribbean

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.

 
 
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.

 
 
Scuba diver and stingray, Grand Cayman Islands

Grand Cayman Vacation Deals

Located near the deepest part of the Caribbean sea, south of Cuba and north of Jamaica, the three Cayman Islands are known for snorkeling, scuba diving, and offshore banking.

 
 
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.

 
 
Frigate Bay, St. Kitts

St. Kitts and Nevis Vacation Deals

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. Martin

St. Martin / St. Maarten Vacation Deals

It's not quite as cosmopolitan as Martinique, nor is it the royalty and rock-star magnet that is chic St Barth - nevertheless, St. Martin has fine French restaurants, European-inspired duty-free shops and glorious beaches.

 
 
Trunk Bay, St John, United States Virgin Islands

U.S. Virgin Islands Vacation Deals

The laid-back vibe and some of the most magnificent coast on earth provide a taste of paradise and a bit of light relief to millions each year.

 
 
1Exclusive Caribbean Hot Deals $100 OFF per booking Offer: Valid on new bookings made 03/09/2020 – 04/19/2020 for select travel 3/9/2020 – 12/20/2020. Minimum 3-night hotel accommodations at participating property and roundtrip airfare required. Savings is per booking and taken at time of booking.
2Rate is per person, based on double occupancy, for check-in on 2/27/2020, Deluxe King Room, & includes roundtrip coach air transportation from BOS or JFK as shown. See General Disclaimer for terms and conditions of air-inclusive offer.
Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]