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.

Hot Deals: Caribbean
$150 OFF 5-Night Vacations

  • Book by 08/11/24 for select travel through 04/30/25
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.

 
 
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.

 
 
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'.

 
 
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.

 
 
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.

 
 
Women on beach deck, 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.

 
 
San Juan, Puerto Rico

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.

 
 
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. Martin

St. Martin / St. Maarten Vacation Deals

This lovely island is the smallest landmass on earth to be shared by two separate nations: France and the Kingdom of the Netherlands.

 
 
Saint Vincent Grenadines

St. Vincent & the Grenadines Vacation Deals

Lying at the southern end of the Caribbean Sea and the Atlantic Ocean, St. Vincent offers a stunning playground far from the stresses of city life.

 
 
Caribbean Hot Deals Offer: Valid on new bookings made 07/01/24 – 08/11/24 for select travel 07/01/2024 – 04/30/2025 unless otherwise indicated. Minimum 5-night stay at participating property and roundtrip airfare required. Savings is per booking and taken at time of booking. 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.]