Jamaica Vacation Deals

Learn all that Jamaica has to offer vacationers and honeymooners, families and lovebirds with Jamaica vacation packages and things to do in Montego Bay, Negril and the reef.

Want more options? See all Jamaica Vacation Packages.

$300 OFF per Booking

Book from 01/19/26 to 03/31/26, travel from 01/19/26 to 12/15/26

Jamaica, Caribbean
Filters
All Vacation Deals
Caribbean
Jamaica

Choose Your Jamaica Vacation Deals

We've found hotels for you based on your selection.
Book now
hotel icon
airplane icon
Sandals Ochi Beach Resort

$200 OFF Caribbean Vacations

map-full icon

Jamaica, Ocho Rios

Book from 09/14/26 to 11/08/26, travel from 09/14/26 to 06/30/27

  • check-small icon

    $200 OFF 5-night vacations

Book this deal View hotel arrow-right icon
Property
Property
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air 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
Princess Senses The Mangrove
star-full icon
star-full icon
star-full icon
star-full icon
star-empty icon

$200 OFF Caribbean Vacations

map-full icon

Green Island

Book from 09/14/26 to 11/08/26, travel from 09/14/26 to 06/30/27

  • check-small icon

    $200 OFF 5-night vacations

Book this deal View hotel arrow-right icon
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air 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
Couples Swept Away
star-full icon
star-full icon
star-full icon
star-full icon
star-half icon

$200 OFF Caribbean Vacations

map-full icon

Jamaica, Negril

Book from 09/14/26 to 11/08/26, travel from 09/14/26 to 06/30/27

  • check-small icon

    $200 OFF 5-night vacations

Book this deal View hotel arrow-right icon
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air 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

$200 OFF Caribbean Vacations

map-full icon

Jamaica, Trelawny

Book from 09/14/26 to 11/08/26, travel from 09/14/26 to 06/30/27

  • check-small icon

    $200 OFF 5-night vacations

Book this deal View hotel arrow-right icon
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air 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
Royalton Hideaway Blue Waters, An Autograph Collection All-Inclusive Resort
star-full icon
star-full icon
star-full icon
star-full icon
star-empty icon

$200 OFF Caribbean Vacations

map-full icon

Jamaica, Trelawny

Book from 09/14/26 to 11/08/26, travel from 09/14/26 to 06/30/27

  • check-small icon

    $200 OFF 5-night vacations

Book this deal View hotel arrow-right icon
Property
Property
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air 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!
info icon

Are you sure you want to
delete this file?

Once deleted, you’ll need to
upload a new agreement form.