Reduced rates, FREE nights, resort credits and more!
Minimum 3-night vacation packages
Book by 3/6/16 for travel through 12/18/16

All Deals Include: Round-trip airfare, Hotel accommodations, Taxes and more

Caribbean Vacation Packages

 from $559
 

Aruba

3 nights with air from $1,035

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Bahamas

4 nights with air from $919

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Dominican Republic

3 nights with air from $839

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Grand Cayman

3 nights with air from $1,315

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Jamaica

3 nights with air from $805

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Puerto Rico

3 nights with air from $559

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St. Kitts and Nevis

3 nights with air from $905

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Saint Lucia

3 nights with air from $1,345

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St. Martin and Sint Maarten

3 nights with air from $1,415

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Turks & Caicos

3 nights with air from $1,125

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US Virgin Islands

3 nights with air from $925

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Rates are based on roundtrip air travel to/from Boston (BOS) for Aruba, St. Kitts and Nevis, St. Lucia, St. Martin and Sint Maarten, Turks & Caicos and US Virgin Islands, Los Angeles (LAX) for Dominican Republic, Manchester (MHT) for Grand Cayman, Philadelphia (PHL) for Jamaica, Pittsburgh (PIT) for Puerto Rico and Providence (PVD) for the Bahamas, and are per person, based on double occupancy. Advertised vacation rate(s) valid for departures 5/16/16 for US Virgin Islands, 5/10/16 for Dominican Republic and 5/11/16 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 - Caribbean Savings Offers: Valid on new bookings made 1/18 - 3/6/16 For travel 1/18 - 12/18/16. Minimum 3-night stay and roundtrip air required. Other restrictions and blackout dates may apply. All offers subject to change or cancellation without notice.
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.]