Jamaica Vacation Packages | Pleasant Holidays

Sandals Ochi Beach Resort

Sandals Resorts - Save up to 65%

Jamaica, Ocho Rios

Book from 01/01/26 to 12/31/26, travel from 01/01/26 to 12/31/27

Save up to 65%

Blackout dates may apply. Certain room categories are applicable. Maximum two-person limit for offer. Offer is based on double occupancy, minimum 3-paid nights' stay required. Promotion is combinable with certain Sandals savings promotions. Group bookings may be subject to space availability. Offer may be changed or withdrawn at any time. Certain conditions apply.

Princess Grand Jamaica

Green Island

Up to $300 OFF Caribbean Vacations

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

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

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.

Up to 62% OFF at Princess Grand Jamaica

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

Up to $300 OFF per booking

FREE room upgrade (based on availability)

Welcome amenity

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 Senses The Mangrove

Up to 59% OFF at Princess Senses The Mangrove

Green Island

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

Up to 59% OFF room rates
Room upgrade (based on availability)
Welcome amenity

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Discount varies based on travel dates, length of stay and room category booked. Blackout dates apply July 16 - 18, 2026; July 23 - 25, 2026; August 6 - 8, 2026; September 17 - 20, 2026; October 16 - 23, 2026; December 23, 2026 - January 10, 2027; January 18 - 23, 2027; February 25 - 27, 2027; May 2 - 6, 2027. Roome upgrade is based on availability. Offer is based on availability and may be discontinued at any time.

Sandals South Coast

Sandals Resorts - Save up to 65%

Jamaica, Savanna La Mar

Book from 01/01/26 to 12/31/26, travel from 01/01/26 to 12/31/27

Save up to 65%

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Blackout dates may apply. Certain room categories are applicable. Maximum two-person limit for offer. Offer is based on double occupancy, minimum 3-paid nights' stay required. Promotion is combinable with certain Sandals savings promotions. Group bookings may be subject to space availability. Offer may be changed or withdrawn at any time. Certain conditions apply.

Sandals Caribbean Cay

Sandals Resorts - Save up to 65%

Jamaica, Montego Bay

Book from 01/01/26 to 12/31/26, travel from 01/01/26 to 12/31/27

Save up to 65%

Book this deal View hotel

Blackout dates may apply. Certain room categories are applicable. Maximum two-person limit for offer. Offer is based on double occupancy, minimum 3-paid nights' stay required. Promotion is combinable with certain Sandals savings promotions. Group bookings may be subject to space availability. Offer may be changed or withdrawn at any time. Certain conditions apply.

Sandals Negril Beach Resort & Spa

Sandals Resorts - Save up to 65%

Jamaica, Negril

Book from 01/01/26 to 12/31/26, travel from 01/01/26 to 12/31/27

Save up to 65%

Book this deal View hotel

Blackout dates may apply. Certain room categories are applicable. Maximum two-person limit for offer. Offer is based on double occupancy, minimum 3-paid nights' stay required. Promotion is combinable with certain Sandals savings promotions. Group bookings may be subject to space availability. Offer may be changed or withdrawn at any time. Certain conditions apply.

Sandals Montego Bay

Sandals Resorts - Save up to 65%

Jamaica, Montego Bay

Book from 01/01/26 to 12/31/26, travel from 01/01/26 to 12/31/27

Save up to 65%

Book this deal View hotel

Blackout dates may apply. Certain room categories are applicable. Maximum two-person limit for offer. Offer is based on double occupancy, minimum 3-paid nights' stay required. Promotion is combinable with certain Sandals savings promotions. Group bookings may be subject to space availability. Offer may be changed or withdrawn at any time. Certain conditions apply.

Couples Swept Away

Up to $300 OFF Caribbean Vacations

Jamaica, Negril

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

$300 OFF per booking for vacations of 7 nights or longer
$200 OFF per booking for vacations of 5-6 nights

Book this deal View hotel

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.

Sandals Dunn's River

Sandals Resorts - Save up to 65%

Jamaica, Ocho Rios

Book from 01/01/26 to 12/31/26, travel from 01/01/26 to 12/31/27

Save up to 65%

Book this deal View hotel

Blackout dates may apply. Certain room categories are applicable. Maximum two-person limit for offer. Offer is based on double occupancy, minimum 3-paid nights' stay required. Promotion is combinable with certain Sandals savings promotions. Group bookings may be subject to space availability. Offer may be changed or withdrawn at any time. Certain conditions apply.

Riu Palace Aquarelle

Up to $300 OFF Caribbean Vacations

Jamaica, Trelawny

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

$300 OFF per booking for vacations of 7 nights or longer
$200 OFF per booking for vacations of 5-6 nights

Book this deal View hotel

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.

Sandals Royal Plantation

Sandals Resorts - Save up to 65%

Jamaica, Ocho Rios

Book from 01/01/26 to 12/31/26, travel from 01/01/26 to 12/31/27

Save up to 65%

Book this deal View hotel

Blackout dates may apply. Certain room categories are applicable. Maximum two-person limit for offer. Offer is based on double occupancy, minimum 3-paid nights' stay required. Promotion is combinable with certain Sandals savings promotions. Group bookings may be subject to space availability. Offer may be changed or withdrawn at any time. Certain conditions apply.

Jamaica Deals

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Choose Your Jamaica Vacation Deal

We've found hotels for you based on your selection.

Sandals Ochi Beach Resort

Princess Grand Jamaica

Up to $300 OFF Caribbean Vacations

Up to 62% OFF at Princess Grand Jamaica

Princess Senses The Mangrove

Sandals South Coast

Sandals Caribbean Cay

Sandals Negril Beach Resort & Spa

Sandals Montego Bay

Couples Swept Away

Sandals Dunn's River

Riu Palace Aquarelle

Sandals Royal Plantation

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Jamaica Deals

Filters

Choose Your Jamaica Vacation Deal

We've found hotels for you based on your selection.

Sandals Ochi Beach Resort

Princess Grand Jamaica

Up to $300 OFF Caribbean Vacations

Up to 62% OFF at Princess Grand Jamaica

Princess Senses The Mangrove

Sandals South Coast

Sandals Caribbean Cay

Sandals Negril Beach Resort & Spa

Sandals Montego Bay

Couples Swept Away

Sandals Dunn's River

Riu Palace Aquarelle

Sandals Royal Plantation

Did you already have a destination in mind?

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