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.

Want more options? See all Caribbean Vacation Packages.

$200 OFF 5-night vacations

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

Serene palm trees and beach, Punta Cana, Caribbean
Serene palm trees and beach, Punta Cana, Caribbean
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Dreams Curacao Resort, Spa & Casino
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$200 OFF Caribbean Vacations

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Curacao

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

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    $200 OFF 5-night vacations

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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.
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Hyatt Ziva Cap Cana
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$200 OFF Caribbean Vacations

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Dom. Republic, Punta Cana

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

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    $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.
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Zemi Miches Punta Cana, All-Inclusive Resort, Curio Collection by Hilton
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$200 OFF Caribbean Vacations

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Miches

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

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    $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.
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Hard Rock Hotel Punta Cana
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$200 OFF Caribbean Vacations

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Dom. Republic, Punta Cana

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
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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.
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Hyatt Zilara Cap Cana
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$200 OFF Caribbean Vacations

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Dom. Republic, Punta Cana

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.
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Majestic Mirage Punta Cana
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$200 OFF Caribbean Vacations

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Dom. Republic, Punta Cana

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.
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Riu Palace Bavaro
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$200 OFF Caribbean Vacations

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Dom. Republic, Punta Cana

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 View
Property View
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.
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Grand Palladium Palace Resort Spa & Casino
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$200 OFF Caribbean Vacations

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Dom. Republic, Punta Cana

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.
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Zoetry Agua Punta Cana
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$200 OFF Caribbean Vacations

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Dom. Republic, Punta Cana

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.
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Melia Punta Cana Beach, A Wellness Inclusive Resort - Adults Only
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$200 OFF Caribbean Vacations

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Dom. Republic, Punta Cana

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.
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Dreams Playa Esmeralda Resort & Spa
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$200 OFF Caribbean Vacations

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Miches

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
Main
Main
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.
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Wyndham Alltra Punta Cana All Inclusive Resort
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$200 OFF Caribbean Vacations

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Dom. Republic, Punta Cana

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.

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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