Jamaica Deals
Dominican Republic Deals
Bahamas Deals
Barbados Deals

Caribbean Vacation Packages

from $519
 
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 a dream selection of custom vacations suited to every taste among these idyllic islands.

$100 OFF per booking

  • Minimum 3-night vacation packages
  • Book by 10/28/18 for travel through 6/30/19
All Deals Include: Round-trip airfare, Hotel accommodations, Taxes and more
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.

3 nights with air from $1,235
 
 
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'.

3 nights with air from $1,035
 
 
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.

3 nights with air from $519
 
 
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.

3 nights with air from $849
 
 
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.

3 nights with air from $745
 
 
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.

3 nights with air from $585
 
 
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.

3 nights with air from $1,089
 
 
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.

3 nights with air from $619
 
 
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.

3 nights with air from $609
 
 
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.

3 nights with air from $1,249
 
 
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.

3 nights with air from $1,045
 
 
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.

3 nights with air from $1,045
 
 
Rates are based on roundtrip air travel from Boston (BOS) to Antigua and Bermuda, New York (JFK) to Barbados, Puerto Rico, St. Kitts & Nevis and Saint Lucia and Miami (MIA) to Aruba, Bahamas, Dominican Republic, Grand Cayman, Jamaica and Turks & Caicos, and are per person, based on double occupancy. Advertised vacation rate(s) valid for departures 11/12/18. Dominican Republic: Rates do not include a $10 per person Tourist Card fee payable upon arrival in the Dominican Republic.
Caribbean - Exclusive $100 OFF per booking offer: Valid on new bookings at participating resorts made 8/27 - 10/28/18 for travel 8/27/18 - 6/30/19. Roundtrip air and minimum 3-night stay required. Savings is per booking, taken at time of booking and reflected in rates shown.
Rates quoted are per person, based on double occupancy unless otherwise stated. Rates for other travel dates may vary. Rates, terms, conditions and itinerary are subject to availability. Certain restrictions apply. Rates shown include government-imposed fees and taxes. Airline fees for optional services, including, but not limited to, baggage fees, may apply. Airline tickets are non-refundable and subject to airline change/cancellation penalties and rules, including pre-flight notification deadlines. Fees and policies vary among airlines and are subject to change without notice. Please contact the airline directly for details and answers to specific questions you may have. Additional restrictions apply. Advertised rates do not include any applicable daily resort or facility fees payable directly to the hotel operator at check-out; such fee amounts will be advised at the time of booking. Where applicable, kids stay free in same room as adults using existing bedding. Occupancy limits apply. Where applicable, kids eat free with full paying adult. Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]