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.

Up to $300 OFF per Booking

Book from 07/06/26 to 09/13/26, travel from 07/06/26 to 06/30/27

Serene palm trees and beach, Punta Cana, Caribbean
Serene palm trees and beach, Punta Cana, Caribbean
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Caribbean

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Couples Swept Away
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Up to $300 OFF Caribbean Vacations

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Jamaica, Negril

Book from 07/06/26 to 09/13/26, travel from 07/06/26 to 06/30/27

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    $300 OFF per booking for vacations of 7 nights or longer

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    $200 OFF per booking for vacations of 5-6 nights

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. SAVE $300 on vacations of 7 nights or longer or SAVE $200 on vacations of 5-6 nights. 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.
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Princess Grand Jamaica
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Up to $300 OFF Caribbean Vacations

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Green Island

Book from 07/06/26 to 09/13/26, travel from 07/06/26 to 06/30/27

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    $300 OFF per booking for vacations of 7 nights or longer

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    $200 OFF per booking for vacations of 5-6 nights

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. SAVE $300 on vacations of 7 nights or longer or SAVE $200 on vacations of 5-6 nights. 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.
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Riu Palace Aquarelle
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Up to $300 OFF Caribbean Vacations

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Jamaica, Trelawny

Book from 07/06/26 to 09/13/26, travel from 07/06/26 to 06/30/27

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    $300 OFF per booking for vacations of 7 nights or longer

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    $200 OFF per booking for vacations of 5-6 nights

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. SAVE $300 on vacations of 7 nights or longer or SAVE $200 on vacations of 5-6 nights. 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.
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JOIA Aruba by Iberostar
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Up to $300 OFF Caribbean Vacations

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Aruba

Book from 07/06/26 to 09/13/26, travel from 07/06/26 to 06/30/27

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    $300 OFF per booking for vacations of 7 nights or longer

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    $200 OFF per booking for vacations of 5-6 nights

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. SAVE $300 on vacations of 7 nights or longer or SAVE $200 on vacations of 5-6 nights. 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.
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Riu Palace Paradise Island
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Up to $300 OFF Caribbean Vacations

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Paradise Island, Bahamas

Book from 07/06/26 to 09/13/26, travel from 07/06/26 to 06/30/27

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    $300 OFF per booking for vacations of 7 nights or longer

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    $200 OFF per booking for vacations of 5-6 nights

Book this deal View hotel arrow-right icon
Pool View
Pool View
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air required. SAVE $300 on vacations of 7 nights or longer or SAVE $200 on vacations of 5-6 nights. 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.
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The Royal at Atlantis
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Up to $300 OFF Caribbean Vacations

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Paradise Island, Bahamas

Book from 07/06/26 to 09/13/26, travel from 07/06/26 to 06/30/27

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    $300 OFF per booking for vacations of 7 nights or longer

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    $200 OFF per booking for vacations of 5-6 nights

Book this deal View hotel arrow-right icon
Exterior
Exterior
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air required. SAVE $300 on vacations of 7 nights or longer or SAVE $200 on vacations of 5-6 nights. 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.
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Royalton Vessence Barbados, an Autograph Collection All-Inclusive Resort
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Up to $300 OFF Caribbean Vacations

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Barbados

Book from 07/06/26 to 09/13/26, travel from 07/06/26 to 06/30/27

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    $300 OFF per booking for vacations of 7 nights or longer

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    $200 OFF per booking for vacations of 5-6 nights

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. SAVE $300 on vacations of 7 nights or longer or SAVE $200 on vacations of 5-6 nights. 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.
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The Ritz-Carlton, Grand Cayman
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Up to $300 OFF Caribbean Vacations

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Grand Cayman

Book from 07/06/26 to 09/13/26, travel from 07/06/26 to 06/30/27

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    $300 OFF per booking for vacations of 7 nights or longer

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    $200 OFF per booking for vacations of 5-6 nights

Book this deal View hotel arrow-right icon
Pool View
Pool View
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air required. SAVE $300 on vacations of 7 nights or longer or SAVE $200 on vacations of 5-6 nights. 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.
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Curacao Marriott Beach Resort
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Up to $300 OFF Caribbean Vacations

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Curacao

Book from 07/06/26 to 09/13/26, travel from 07/06/26 to 06/30/27

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    $300 OFF per booking for vacations of 7 nights or longer

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    $200 OFF per booking for vacations of 5-6 nights

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. SAVE $300 on vacations of 7 nights or longer or SAVE $200 on vacations of 5-6 nights. 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.
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Moon Palace The Grand Punta Cana
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Up to $300 OFF Caribbean Vacations

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Dom. Republic, Punta Cana

Book from 07/06/26 to 09/13/26, travel from 07/06/26 to 06/30/27

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    $300 OFF per booking for vacations of 7 nights or longer

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    $200 OFF per booking for vacations of 5-6 nights

Book this deal View hotel arrow-right icon
Main
Main
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air required. SAVE $300 on vacations of 7 nights or longer or SAVE $200 on vacations of 5-6 nights. 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.
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Zemi Miches Punta Cana, All-Inclusive Resort, Curio Collection by Hilton
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Up to $300 OFF Caribbean Vacations

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Miches

Book from 07/06/26 to 09/13/26, travel from 07/06/26 to 06/30/27

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    $300 OFF per booking for vacations of 7 nights or longer

  • check-small icon

    $200 OFF per booking for vacations of 5-6 nights

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. SAVE $300 on vacations of 7 nights or longer or SAVE $200 on vacations of 5-6 nights. 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.
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Hard Rock Hotel Punta Cana
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Up to $300 OFF Caribbean Vacations

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Dom. Republic, Punta Cana

Book from 07/06/26 to 09/13/26, travel from 07/06/26 to 06/30/27

  • check-small icon

    $300 OFF per booking for vacations of 7 nights or longer

  • check-small icon

    $200 OFF per booking for vacations of 5-6 nights

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. SAVE $300 on vacations of 7 nights or longer or SAVE $200 on vacations of 5-6 nights. 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.

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Call 1-800-742-9244
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