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.

$200 OFF per Booking

Book from 03/16/26 to 05/10/26, travel from 03/16/26 to 12/15/26

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

Choose Your Caribbean Vacation Deals

We've found hotels for you based on your selection.
Book now
hotel icon
airplane icon
Beaches Negril Resort & Spa

Caribbean - $200 OFF per booking

map-full icon

Jamaica, Negril

Book from 03/16/26 to 05/10/26, travel from 03/16/26 to 12/15/26

  • check-small icon

    $200 OFF per booking

Book this deal View hotel arrow-right icon
Minimum 5-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

Caribbean - $200 OFF per booking

map-full icon

Aruba

Book from 03/16/26 to 05/10/26, travel from 03/16/26 to 12/15/26

  • check-small icon

    $200 OFF per booking

Book this deal View hotel arrow-right icon
Minimum 5-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 Club Barbados Resort & Spa
star-full icon
star-full icon
star-full icon
star-half icon
star-empty icon

Caribbean - $200 OFF per booking

map-full icon

Barbados

Book from 03/16/26 to 05/10/26, travel from 03/16/26 to 12/15/26

  • check-small icon

    $200 OFF per booking

Book this deal View hotel arrow-right icon
Property
Property
Minimum 5-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

Caribbean - $200 OFF per booking

map-full icon

Curacao

Book from 03/16/26 to 05/10/26, travel from 03/16/26 to 12/15/26

  • check-small icon

    $200 OFF per booking

Book this deal View hotel arrow-right icon
Exterior
Exterior
Minimum 5-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
Zemi Miches Punta Cana, All-Inclusive Resort, Curio Collection by Hilton
star-full icon
star-full icon
star-full icon
star-full icon
star-half icon

Caribbean - $200 OFF per booking

map-full icon

Miches

Book from 03/16/26 to 05/10/26, travel from 03/16/26 to 12/15/26

  • check-small icon

    $200 OFF per booking

Book this deal View hotel arrow-right icon
Minimum 5-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 Zilara Cap Cana
star-full icon
star-full icon
star-full icon
star-full icon
star-half icon

Caribbean - $200 OFF per booking

map-full icon

Dom. Republic, Punta Cana

Book from 03/16/26 to 05/10/26, travel from 03/16/26 to 12/15/26

  • check-small icon

    $200 OFF per booking

Book this deal View hotel arrow-right icon
Minimum 5-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
Majestic Mirage Punta Cana
star-full icon
star-full icon
star-full icon
star-full icon
star-half icon

Caribbean - $200 OFF per booking

map-full icon

Dom. Republic, Punta Cana

Book from 03/16/26 to 05/10/26, travel from 03/16/26 to 12/15/26

  • check-small icon

    $200 OFF per booking

Book this deal View hotel arrow-right icon
Property
Property
Minimum 5-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 Republica
star-full icon
star-full icon
star-full icon
star-full icon
star-empty icon

Caribbean - $200 OFF per booking

map-full icon

Dom. Republic, Punta Cana

Book from 03/16/26 to 05/10/26, travel from 03/16/26 to 12/15/26

  • check-small icon

    $200 OFF per booking

Book this deal View hotel arrow-right icon
Beach View
Beach View
Minimum 5-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
Lopesan Costa Bavaro Resort, Spa & Casino
star-full icon
star-full icon
star-full icon
star-full icon
star-empty icon

Caribbean - $200 OFF per booking

map-full icon

Dom. Republic, Punta Cana

Book from 03/16/26 to 05/10/26, travel from 03/16/26 to 12/15/26

  • check-small icon

    $200 OFF per booking

Book this deal View hotel arrow-right icon
Exterior
Exterior
Minimum 5-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 Agua Punta Cana
star-full icon
star-full icon
star-full icon
star-full icon
star-half icon

Caribbean - $200 OFF per booking

map-full icon

Dom. Republic, Punta Cana

Book from 03/16/26 to 05/10/26, travel from 03/16/26 to 12/15/26

  • check-small icon

    $200 OFF per booking

Book this deal View hotel arrow-right icon
Property
Property
Minimum 5-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
Secrets La Romana Resort & Spa
star-full icon
star-full icon
star-full icon
star-full icon
star-empty icon

Caribbean - $200 OFF per booking

map-full icon

Dom. Republic, La Romana

Book from 03/16/26 to 05/10/26, travel from 03/16/26 to 12/15/26

  • check-small icon

    $200 OFF per booking

Book this deal View hotel arrow-right icon
Property
Property
Minimum 5-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 Bavaro Suites Resort & Spa
star-full icon
star-full icon
star-full icon
star-full icon
star-empty icon

Caribbean - $200 OFF per booking

map-full icon

Dom. Republic, Punta Cana

Book from 03/16/26 to 05/10/26, travel from 03/16/26 to 12/15/26

  • check-small icon

    $200 OFF per booking

Book this deal View hotel arrow-right icon
Property View
Property View
Minimum 5-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.
Beach - Samana | Dominican Republic

Want to see available
rooms and prices?

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!