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 - Christmas in July SALE
Up to 60% OFF room rates, FREE room upgrades, kids stay FREE offers and more

  • Book by 8/2/20 for select travel through 12/31/20
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'.

 
 
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.

 
 
St. Lucia Pitons

Saint Lucia Vacation Deals

With pristine rainforests, palm-fringed beaches and the majestic Pitons forming a stunning backdrop, Saint Lucia will captivate even the most seasoned travelers.

 
 
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 list.

 
 
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.

 
 
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.

 
 
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.

 
 
Caribbean Christmas in July Sale: Valid on new bookings made 07/06/2020 – 08/02/2020 for select travel 07/06/2020 – 12/31/2020. Offers vary by hotel and travel dates, and may be category-specific, require advance booking, be restricted to specific days of the week and/or require a minimum night stay. Booking and travel dates vary by hotel. Certain restrictions and blackout dates may apply. Subject to availability.
Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]