Caribbean Island
Aerial view of a Caribbean island
arrow-down icon
Book your vacation now
All destinations
Caribbean
Deals
Filters

Choose Your Caribbean Vacation Deal

We've found hotels for you based on your selection.
Book now
hotel icon
airplane icon
Dreams La Romana Resort & Spa
star-full icon
star-full icon
star-full icon
star-full icon
star-empty icon

Up to $300 OFF Caribbean Vacations

map-full icon

Dom. Republic, La Romana

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

  • check-small icon

    $300 OFF per booking for vacations of 7 nights or longer

  • check-small icon

    $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.
hotel icon
airplane icon
Grand Palladium Bavaro Suites Resort & Spa
star-full icon
star-full icon
star-full icon
star-full icon
star-empty icon

Up to $300 OFF Caribbean Vacations

map-full icon

Dom. Republic, Punta Cana

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

  • check-small icon

    $300 OFF per booking for vacations of 7 nights or longer

  • check-small icon

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

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. 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.
hotel icon
airplane icon
Dreams Cap Cana Resort & Spa
star-full icon
star-full icon
star-full icon
star-full icon
star-half icon

Up to $300 OFF Caribbean Vacations

map-full icon

Dom. Republic, Punta Cana

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

  • check-small icon

    $300 OFF per booking for vacations of 7 nights or longer

  • check-small icon

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

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. 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.
hotel icon
airplane icon
Dreams Playa Esmeralda Resort & Spa
star-full icon
star-full icon
star-full icon
star-full icon
star-half icon

Up to $300 OFF Caribbean Vacations

map-full icon

Miches

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

  • check-small icon

    $300 OFF per booking for vacations of 7 nights or longer

  • check-small icon

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

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. 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.
hotel icon
airplane icon
Secrets Playa Esmeralda Resort & Spa
star-full icon
star-full icon
star-full icon
star-full icon
star-half icon

Up to $300 OFF Caribbean Vacations

map-full icon

Miches

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

  • check-small icon

    $300 OFF per booking for vacations of 7 nights or longer

  • check-small icon

    $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.
hotel icon
airplane icon
San Juan Marriott Resort & Stellaris Casino
star-full icon
star-full icon
star-full icon
star-full icon
star-empty icon

Up to $300 OFF Caribbean Vacations

map-full icon

San Juan, Puerto Rico

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

  • check-small icon

    $300 OFF per booking for vacations of 7 nights or longer

  • check-small icon

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

Book this deal View hotel arrow-right icon
Beach View
Beach 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.
hotel icon
airplane icon
Sandals Grande St.Lucian Spa & Beach Resort

Sandals Resorts - Save up to 65%

map-full icon

St. Lucia

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

  • check-small icon

    Save up to 65%

Book this deal View hotel arrow-right icon
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.
hotel icon
airplane icon
Sandals Regency La Toc

Sandals Resorts - Save up to 65%

map-full icon

St. Lucia

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

  • check-small icon

    Save up to 65%

Book this deal View hotel arrow-right icon
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.
hotel icon
airplane icon
Sandals Halcyon Beach Resort & Spa

Sandals Resorts - Save up to 65%

map-full icon

St. Lucia

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

  • check-small icon

    Save up to 65%

Book this deal View hotel arrow-right icon
Property
Property
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.
Windjammer Landing Resort and Residences
star-full icon
star-full icon
star-full icon
star-full icon
star-empty icon
map-full icon

St. Lucia

Up to 35% OFF at Windjammer Landing

Book from 07/01/26 to 12/18/27, travel through

Book this deal View hotel arrow-right icon
Discount varies based on travel dates, length of stay and room category booked. Offer is based on availability and may be discontinued at any time.
Up to $300 OFF Caribbean Vacations

Book from 07/06/26 to 06/30/27, travel through

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.
Property View
Property View
hotel icon
airplane icon
Sonesta Ocean Point Resort & Spa
star-full icon
star-full icon
star-full icon
star-full icon
star-empty icon

Up to $300 OFF Caribbean Vacations

map-full icon

Saint Maarten, Netherlands

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

  • check-small icon

    $300 OFF per booking for vacations of 7 nights or longer

  • check-small icon

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

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. 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.
hotel icon
airplane icon
Buoy Haus Beach Resort St. Thomas, Autograph Collection
star-full icon
star-full icon
star-full icon
star-full icon
star-half icon

Up to $300 OFF Caribbean Vacations

map-full icon

St. Thomas, USVI

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

  • check-small icon

    $300 OFF per booking for vacations of 7 nights or longer

  • check-small icon

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

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. 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.
Serene palm trees and beach, Punta Cana, Caribbean
Serene palm trees and beach, Punta Cana, Caribbean

Did you already have
a destination in mind?

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.

support icon

Contact us

support icon

Any questions ?

Our travel advisors will be happy to help!

Call 1-800-742-9244
email icon
net.support@pleasant.net

Copied!
info icon

Are you sure you want to
delete this file?

Once deleted, you’ll need to
upload a new agreement form.