SAVE $100 per booking
Minimum 3-night vacation packages
Book by 11/1/15 for travel through 6/30/16

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

Caribbean Vacation Packages

 from $499


3 nights with air from $745

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3 nights with air from $859

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Dominican Republic

3 nights with air from $565

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3 nights with air from $829

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Puerto Rico

3 nights with air from $499

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St. Lucia

3 nights with air from $1,805

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Turks & Caicos

3 nights with air from $1,105

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US Virgin Islands

3 nights with air from $645

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Rates are based on roundtrip air travel to/from Boston (BOS) for Puerto Rico, US Virgin Islands, Aruba, Turks & Caicos and St. Lucia, Philadelphia (PHL) for Jamaica, Pittsburgh (PIT) for Dominican Republic and Providence (PVD) for Bahamas, and are per person, based on double occupancy. Advertised vacation rate(s) valid for departures 11/15/15 for US Virgin Islands, 11/16/15 for Jamaica, Aruba and Dominican Republic and 11/17/15 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 - $100 Savings Offer: Valid on new bookings made 8/31 - 11/1/15 for travel 8/31/15 - 6/30/16. Minimum 3-night stay and roundtrip air required. Savings is per booking and taken at time of booking. Other 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.]