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Caribbean Vacation Packages from $535

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Fall Travel Sale: Buy One Activity,
Get One Activity FREE
On minimum 3-night vacation packages in
Aruba, Dominica, Jamaica and Dominican Republic
Book by 8/9/15 for travel through 11/19/15
Two FREE Days of Airport Parking at
The Parking Spot
On minimum 3-night vacation packages for
Aruba, Dominica, Jamaica and Dominican Republic
Valid only from select gateways
Book by 8/9/15 for travel 8/15 - 11/19/15
Pleasant Caribbean Holidays

3 nights from $839


4 nights from $695

Dominican Republic

3 nights from $645

More Great Deals

Puerto Rico

3 nights from $535


3 nights from $695


3 nights from $775

Rates are based on roundtrip air travel to/from Orlando (MCO) for Puerto Rico, Bahamas, Jamaica and Aruba, Miami (MIA) for Dominican Republic and New York (JFK) for Dominica. Rates are valid for for select travel 11/17/15 for Bahamas, 10/15/15 for Dominica, 10/19/15 for Dominican Republic and 10/6/15 for all other destinations. 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. Rates do not include a $10 per person Tourist Card fee payable upon arrival in the Dominican Republic.

BOGO Activity Offer: Valid on new bookings made 7/6 - 8/9/15 for travel 7/6 - 11/19/15. Requires roundtrip air from the United States. Minimum night stay may be required and varies by resort. Offer valid on select activities detailed above. At time of booking, a voucher will be generated for the BOGO activity offer; the voucher can then be redeemed by the traveler or his/her travel agent by calling 1-888-229-7770. When traveler purchases the identified activity for his/her Caribbean vacation through Pleasant Holidays, he/she will receive a second identified activity free of charge for that same vacation. Fees and surcharges are excluded and must be paid for both tours. Limit of one complimentary activity per booking. Certain restrictions apply.

FREE Parking Offer: Valid on new bookings made 7/6 - 8/9/15 for travel 8/15 - 11/19/15; bookings must include minimum 3 nights' hotel accommodation at a participating hotel and roundtrip airfare. Travelers receive two (2) days of complimentary Self-Parking at The Parking Spot (TPS). Offer valid at all TPS locations nationwide including ATL, AUS, BNA, BUF, BWI, CMH, DAL, DEN, DFW, EWR, HOU, IAH, JFK, LAX, LGA, MCI, MCO, PHL, PHX, PIT and STL and is combinable with Pleasant Holidays' savings of up to 25% on TPS parking, which may be applied for additional days. Fees for additional days will be payable directly to TPS upon exit. Travelers will receive a card with their final travel documents that is pre-loaded with two free days of parking. Card must be registered online to receive a certificate that must be printed and presented at the TPS location along with the card. Limited to use of one card per stay. Two-day free parking offer is NOT valid for Valet Parking; value of two-day free parking card cannot be applied towards the purchase of Valet Parking. Card is not redeemable for cash, has no cash value for any unused days and is non-transferrable. Not responsible if lost or stolen. All offers subject to change or cancellation without notice Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]

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