Caribbean Deals
Last-Minute Holiday Savings
Book by 11/26/17 for travel through 1/7/18
All Deals Include: Round-trip airfare, Hotel accommodations, Taxes and more

Caribbean Vacation Packages

 from $759


3 nights with air from $1,049

Book Now


3 nights with air from $759

Book Now

Dominican Republic

3 nights with air from $979

Book Now

Grand Cayman

3 nights with air from $1,465

Book Now


3 nights with air from $1,119

Book Now

St. Kitts and Nevis

5 nights with air from $4,605

Book Now

Saint Lucia

3 nights with air from $1,705

Book Now
Share With
Rates are based on roundtrip air travel from Boston (BOS) to Saint Lucia, New York (JFK) to St. Kitts and Nevis and Miami (MIA) to Aruba, Bahamas, Dominican Republic, Grand Cayman and Jamaica and are per person, based on double occupancy. Advertised vacation rate(s) valid for departures 12/20/17 for Grand Cayman, 1/2/18 for St. Kitts and Nevis and 1/3/18 for all other destinations. Dominican Republic: Rates do not include a $10 per person Tourist Card fee payable upon arrival in the Dominican Republic.
Caribbean - Last-Minute Holiday Savings Offers: Valid on new bookings at participating resorts made 10/30 - 11/26/17 for travel through 1/7/18. Offers and minimum night stays vary by hotel and may be category-specific, require advance booking, be restricted to specific days of the week and/or require a minimum night stay. Booking and travel dates vary by hotel. Certain restrictions and blackout dates may apply.
Rates quoted are per person, based on double occupancy unless otherwise stated. Rates for other travel dates may vary. Rates, terms, conditions and itinerary are subject to availability. Certain restrictions apply. Rates shown include government-imposed fees and taxes. Airline fees for optional services, including, but not limited to, baggage fees, may apply. Airline tickets are non-refundable and subject to airline change/cancellation penalties and rules, including pre-flight notification deadlines. Fees and policies vary among airlines and are subject to change without notice. Please contact the airline directly for details and answers to specific questions you may have. Additional restrictions apply. Advertised rates do not include any applicable daily resort or facility fees payable directly to the hotel operator at check-out; such fee amounts will be advised at the time of booking. Where applicable, kids stay free in same room as adults using existing bedding. Occupancy limits apply. Where applicable, kids eat free with full paying adult. Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]