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
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Beaches Turks & Caicos Resort Villages & Spa

$100 OFF Caribbean Vacations

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Turks & Caicos

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

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    $100 OFF per booking

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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.
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Salterra, a Luxury Collection Resort & Spa, South Caicos
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$100 OFF Caribbean Vacations

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South Caicos

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

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    $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.
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Galley Bay Resort & Spa
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$100 OFF Caribbean Vacations

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Antigua

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

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    $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.
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Royalton CHIC Antigua, An Autograph Collection All-Inclusive Resort-Adults
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$100 OFF Caribbean Vacations

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Antigua

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

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    $100 OFF per booking

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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.
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The Verandah Antigua
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$100 OFF Caribbean Vacations

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Antigua

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

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    $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.
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Sandals Grenada Resort & Spa

$100 OFF Caribbean Vacations

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Grenada

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

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    $100 OFF per booking

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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.
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The Rockley
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$100 OFF Caribbean Vacations

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Barbados

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

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    $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.
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Hyatt Vivid Punta Cana
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$100 OFF Caribbean Vacations

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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.
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Lopesan Serenity Bay Resort, Spa & Casino
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$100 OFF Caribbean Vacations

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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.

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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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