Jamaica Deals
Dominican Republic Deals
Bahamas Deals
Barbados Deals

Caribbean Vacation Packages

 from $619
 
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.

The Best Offers for Summer
FREE nights, reduced rates, resort credits, kids stay FREE offers, and more

  • Book by 7/1/18 for travel through 9/3/18
All Deals Include: Round-trip airfare, Hotel accommodations, Taxes and more
Anguilla Beach

Anguilla Vacation Deals

If sand and sea are high on your vacation wish list, Anguilla is the perfect destination for you. The island boasts 33 beautiful powdery beaches along tranquil waters, each with a distinct vibe.

3 nights with air from $319
 
 
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 $319
 
 
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 $619
 
 
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 $619
 
 
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 $619
 
 
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 $619
 
 
Baths National Park, Virgin Gorda, British Virgin Islands

British Virgin Islands Vacation Deals

Explore a century-old shipwreck, experience world-class sportfishing or simply soak in the radiant sun and wide skies.

3 nights with air from $619
 
 
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.

3 nights with air from $619
 
 
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 $619
 
 
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.

3 nights with air from $619
 
 
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 $619
 
 
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
 
 
Martinique beach

Martinique Vacation Deals

The island of Martinique is a welcoming mix of European and Caribbean cultures.

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 $619
 
 
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 $619
 
 
St. Barth

St. Barth Vacation Deals

Visitors to St. Barts are captivated by its endless sunshine, pristine beauty and chic vibe.

3 nights with air from $619
 
 
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.

3 nights with air from $619
 
 
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 $849

 
 
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.

3 nights with air from $849

 
 

Enjoy Caribbean Vacations with the Caribbean at Pleasant Holidays

 
Founded in 1959, Pleasant Holidays is one of the largest tour operators in the U.S., offering vacation packages, flights, hotels, cruises, car rentals, travel protection and related travel services to the world’s most popular destinations including the Caribbean.
Caribbean - The Best Deals: Valid on new bookings at participating resorts made 7/2 - 7/29/18 for select travel through 12/21/18. Offers vary by hotel 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. Blackout dates may apply.