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 Deals.

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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Princess Grand Jamaica
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Up to 62% OFF at Princess Grand Jamaica

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Green Island

Book from 07/12/26 to 09/13/26, travel from 08/28/26 to 12/22/27

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    Up to 62% OFF room rates

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    Up to $300 OFF per booking

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    FREE room upgrade (based on availability)

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    Welcome amenity

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Discount varies based on travel dates, length of stay and room category booked. Blackout dates apply for travel July 6 - 19, 2026; July 22 - 31, 2026; August 6 - 9, 14 - 18, 21 - 22, 26 - 27, 2026; October 16 - 23, 2026; December 23, 2026 - January 10, 2027; April 13 - 16, 2027; June 18 - 22, 2027. Room upgrade is based on availability. Offer is based on availability and may be discontinued 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

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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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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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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

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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, FREE Breakfast & More at The Royal at Atlantis

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Paradise Island, Bahamas

Book from 07/15/26 to 09/13/26, travel from 08/09/26 to 01/31/27

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    Up to 35% OFF room rates

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    Up to $300 OFF per booking

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    FREE daily breakfast for two

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    $250 Resort Credit per room

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Up to 35% OFF Offer: a minimum of four consecutive nights is required. Applicable to all room categories. Discount varies based on travel dates and room category booked. Free daily breakfast for two (2) valued up to $100 per day, including 10% VAT and 15% Gratuities. Resort credit may not be used for laundry service or at any of the following outlets: Atlantis LIVE, Mandara Spa, Ocean Club Golf Course, the Casino, Marina Starbucks, The Dilly Club, Claudio’s, the Atlantis Signature shops or any other retail shops. It may not be used on gratuities for food and beverage consumption, in-room movies or phone calls, transportation/transfers, or taxes. Blackout dates apply Nov 21, 2026 – Nov 27, 2026, and Dec 16, 2026 – Jan 1, 2027. Up to $300 OFF per booking offer: 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
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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
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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

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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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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

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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
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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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