Caribbean Vacation Deals

In the Caribbean, you can hike through national parks and scuba dive along underwater mountains. But perhaps your idea of the perfect island vacation is to plunk yourself down on the sands with a frosted drink in hand. The Caribbean has something for everyone.

$100 OFF per Booking

Book from 05/11/26 to 07/05/26, travel from 05/11/26 to 03/31/27

Serene palm trees and beach, Punta Cana, Caribbean
Serene palm trees and beach, Punta Cana, Caribbean
Filters
All Vacation Deals
Caribbean

Choose Your Caribbean Vacation Deals

We've found hotels for you based on your selection.
Book now
hotel icon
airplane icon
Couples Tower Isle
star-full icon
star-full icon
star-full icon
star-full icon
star-half icon

$100 OFF Caribbean Vacations

map-full icon

Jamaica, Ocho Rios

Book from 05/11/26 to 07/05/26, travel from 05/11/26 to 03/31/27

  • check-small icon

    $100 OFF per booking

Book this deal View hotel arrow-right icon
Minimum 3-night hotel accommodations at participating property and round-trip airfare required. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
hotel icon
airplane icon
Riu Palace Aquarelle
star-full icon
star-full icon
star-full icon
star-full icon
star-empty icon

$100 OFF Caribbean Vacations

map-full icon

Jamaica, Trelawny

Book from 05/11/26 to 07/05/26, travel from 05/11/26 to 03/31/27

  • check-small icon

    $100 OFF per booking

Book this deal View hotel arrow-right icon
Main
Main
Minimum 3-night hotel accommodations at participating property and round-trip airfare required. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
hotel icon
airplane icon
Ocean Coral Spring
star-full icon
star-full icon
star-full icon
star-full icon
star-empty icon

$100 OFF Caribbean Vacations

map-full icon

Jamaica, Trelawny

Book from 05/11/26 to 07/05/26, travel from 05/11/26 to 03/31/27

  • check-small icon

    $100 OFF per booking

Book this deal View hotel arrow-right icon
Resort
Minimum 3-night hotel accommodations at participating property and round-trip airfare required. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
hotel icon
airplane icon
Grand Palladium Jamaica Resort & Spa
star-full icon
star-full icon
star-full icon
star-full icon
star-empty icon

$100 OFF Caribbean Vacations

map-full icon

Jamaica, Lucea

Book from 05/11/26 to 07/05/26, travel from 05/11/26 to 03/31/27

  • check-small icon

    $100 OFF per booking

Book this deal View hotel arrow-right icon
Pool
Pool
Minimum 3-night hotel accommodations at participating property and round-trip airfare required. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
hotel icon
airplane icon
Riu Negril
star-full icon
star-full icon
star-full icon
star-full icon
star-empty icon

$100 OFF Caribbean Vacations

map-full icon

Jamaica, Negril

Book from 05/11/26 to 07/05/26, travel from 05/11/26 to 03/31/27

  • check-small icon

    $100 OFF per booking

Book this deal View hotel arrow-right icon
Minimum 3-night hotel accommodations at participating property and round-trip airfare required. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
hotel icon
airplane icon
Aruba Marriott Resort & Stellaris Casino
star-full icon
star-full icon
star-full icon
star-full icon
star-empty icon

$100 OFF Caribbean Vacations

map-full icon

Aruba

Book from 05/11/26 to 07/05/26, travel from 05/11/26 to 03/31/27

  • check-small icon

    $100 OFF per booking

Book this deal View hotel arrow-right icon
Property
Property
Minimum 3-night hotel accommodations at participating property and round-trip airfare required. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
hotel icon
airplane icon
JOIA Aruba by Iberostar
star-full icon
star-full icon
star-full icon
star-full icon
star-half icon

$100 OFF Caribbean Vacations

map-full icon

Aruba

Book from 05/11/26 to 07/05/26, travel from 05/11/26 to 03/31/27

  • check-small icon

    $100 OFF per booking

Book this deal View hotel arrow-right icon
Minimum 3-night hotel accommodations at participating property and round-trip airfare required. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
hotel icon
airplane icon
The Royal at Atlantis
star-full icon
star-full icon
star-full icon
star-full icon
star-empty icon

$100 OFF Caribbean Vacations

map-full icon

Paradise Island, Bahamas

Book from 05/11/26 to 07/05/26, travel from 05/11/26 to 03/31/27

  • check-small icon

    $100 OFF per booking

Book this deal View hotel arrow-right icon
Exterior
Exterior
Minimum 3-night hotel accommodations at participating property and round-trip airfare required. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
hotel icon
airplane icon
Sandals Barbados

$100 OFF Caribbean Vacations

map-full icon

Barbados

Book from 05/11/26 to 07/05/26, travel from 05/11/26 to 03/31/27

  • check-small icon

    $100 OFF per booking

Book this deal View hotel arrow-right icon
Minimum 3-night hotel accommodations at participating property and round-trip airfare required. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
hotel icon
airplane icon
Sandals Royal Curacao

$100 OFF Caribbean Vacations

map-full icon

Curacao

Book from 05/11/26 to 07/05/26, travel from 05/11/26 to 03/31/27

  • check-small icon

    $100 OFF per booking

Book this deal View hotel arrow-right icon
Minimum 3-night hotel accommodations at participating property and round-trip airfare required. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
hotel icon
airplane icon
Zoetry Curacao Resort & Spa
star-full icon
star-full icon
star-full icon
star-full icon
star-half icon

$100 OFF Caribbean Vacations

map-full icon

Curacao

Book from 05/11/26 to 07/05/26, travel from 05/11/26 to 03/31/27

  • check-small icon

    $100 OFF per booking

Book this deal View hotel arrow-right icon
Exterior
Exterior
Minimum 3-night hotel accommodations at participating property and round-trip airfare required. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
hotel icon
airplane icon
Hyatt Ziva Cap Cana
star-full icon
star-full icon
star-full icon
star-full icon
star-half icon

$100 OFF Caribbean Vacations

map-full icon

Dom. Republic, Punta Cana

Book from 05/11/26 to 07/05/26, travel from 05/11/26 to 03/31/27

  • check-small icon

    $100 OFF per booking

Book this deal View hotel arrow-right icon
Minimum 3-night hotel accommodations at participating property and round-trip airfare required. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.

You will be transferred to our traditional site.

We are currently working on enhancements to this part of our website. A new version will be available soon. Don’t worry – switching over will not interrupt your booking.

Welcome to the all-new Pleasant Holidays booking experience !

You can now plan your next vacation with our exciting new booking engine. Some advanced features are still being developed, and selecting these options may require you to return to our traditional booking experience. Don’t worry – switching over will not interrupt your booking.

We've updated your online experience to make sure you can get your dream vacation. Since our makeover is still in progress, you may experience shifts from our traditional booking experience to our new one.

Are you a travel agent ? We are also working on a new digital experience specifically for travel professionals and we can’t wait for you to see it. Until then, please continue to use the traditional experience here: Pleasantagent.com.

You are a travel agent? Go to Pleasantagent.com. and enjoy the optimized experience for travel professionals.

support icon

Contact us

support icon

Any questions ?

Our travel advisors will be happy to help!

Call 1-800-742-9244
email icon
net.support@pleasant.net

Copied!