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.

$300 OFF per Booking

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

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

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Sandals Ochi Beach Resort

$300 OFF Caribbean Vacations

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Jamaica, Ocho Rios

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

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    $300 OFF 5-night vacations

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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.
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Riu Montego Bay
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$300 OFF Caribbean Vacations

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Jamaica, Montego Bay

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

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    $300 OFF 5-night vacations

Book this deal View hotel arrow-right icon
Aerial
Aerial
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.
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Sandals Negril Beach Resort & Spa

$300 OFF Caribbean Vacations

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Jamaica, Negril

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

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    $300 OFF 5-night vacations

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.
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Couples Swept Away
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$300 OFF Caribbean Vacations

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Jamaica, Negril

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

  • check-small icon

    $300 OFF 5-night vacations

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.
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Sandals Dunn's River

$300 OFF Caribbean Vacations

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Jamaica, Ocho Rios

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

  • check-small icon

    $300 OFF 5-night vacations

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.
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Moon Palace Jamaica
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$300 OFF Caribbean Vacations

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Jamaica, Ocho Rios

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

  • check-small icon

    $300 OFF 5-night vacations

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.
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Ocean Eden Bay
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$300 OFF Caribbean Vacations

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Jamaica, Montego Bay

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

  • check-small icon

    $300 OFF 5-night vacations

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.
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Riu Palace Tropical Bay
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$300 OFF Caribbean Vacations

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Jamaica, Negril

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

  • check-small icon

    $300 OFF 5-night vacations

Book this deal View hotel arrow-right icon
Resort
Resort
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.
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Couples Negril
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$300 OFF Caribbean Vacations

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Jamaica, Negril

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

  • check-small icon

    $300 OFF 5-night vacations

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.
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Couples Tower Isle
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$300 OFF Caribbean Vacations

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Jamaica, Ocho Rios

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

  • check-small icon

    $300 OFF 5-night vacations

Book this deal View hotel arrow-right icon
Main
Main
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.
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Riu Palace Jamaica
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$300 OFF Caribbean Vacations

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Jamaica, Montego Bay

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

  • check-small icon

    $300 OFF 5-night vacations

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.
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JOIA Rose Hall by Iberostar
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$300 OFF Caribbean Vacations

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Jamaica, Rose Hall

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

  • check-small icon

    $300 OFF 5-night vacations

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.
Beach - Samana | Dominican Republic

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