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.

Level Up Your Caribbean Vacation with a FREE Room Upgrade

  • Book by 06/29/25 for travel through 02/28/26
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 Lucea Beach

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.

 
 
Aruba

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

More than 700 islands and 2,400 cays, or smaller islands, make up the gorgeous, sunswept archipelago known as The Bahamas. This idyllic getaway is favorite vacation spot for sun-worshippers and adventurers alike. Enjoy prime snorkeling and scuba diving, beautiful colonial architecture and endless views of sparkling turquoise seas.

 
 
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. 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.

 
 
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 historic 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.

 
 
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.

 
 

Caribbean FREE Room Upgrade Offer: FREE room upgrade to the next highest category, subject to availability at time of booking. Valid for new bookings made by 06/29/2025 for travel through 02/28/2026 unless otherwise stated. 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. This entire offer is based on availability and can be modified or closed out at any time.

Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]