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 Vacation Sale
Hotel discounts, FREE nights, resort credits and more

  • Book by 12/6/20 for select travel through 1/6/21
Vacations Include: Round-trip flights, hotel accommodations, taxes and more
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.

 
 
Chaplin Bay, Bermuda

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.

 
 
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.

 
 
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. 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.

 
 
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.

 
 
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.

 
 
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.

 
 
Caribbean Winter Vacation Sale: Valid on new bookings made 11/2/20-12/6/20 for select travel 11/2/20-1/6/21. Minimum 3-night hotel accommodations at participating property and roundtrip airfare required. Savings is per booking, taken at time of booking and reflected in rates shown.
Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]