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Caribbean Vacation Packages from $459

BOOK ONLINE OR CALL 1-800-742-9244
SAVE up to $100 per booking!
On minimum 3-night vacation packages
Book by 11/30/14 for travel through 12/17/15
$200 Instant Air Credit
Valid from select Midwest gateways*
Book by 12/31/14 for travel anytime
Pleasant Caribbean Holidays

3 nights from $675


3 nights from $589

Dominican Republic

3 nights from $619

More Great Deals

Puerto Rico

3 nights from $459

St. Lucia

3 nights from $945

Turks & Caicos

3 nights from $1,269


3 nights from $1,105

Grand Cayman

3 nights from $1,385


3 nights from $1,535

St. Kitts and Nevis

4 nights from $1,339

St. Martin

3 nights from $995

US Virgin Islands

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Rates are based on roundtrip air travel to/from Chicago (ORD) departures to Antigua, and St. Kitts & Nevis, Cleveland (CLE) departures to Aruba and Puerto Rico; Miami (MIA) to Bahamas and Dominican Republic, New York (JFK) departures to Cayman Islands, Turks & Caicos and St. Martin/Maartin, Minneapolis (MSP) departures to Jamaica and Boston (BOS) departures to St. Lucia and are per person, based on double occupancy. Advertised vacation rate(s) valid for departure 5/4/15 for Jamaica and St. Lucia, 4/23/15 for Turks & Caicos and St. Kitts/Nevis and 1/26/15 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.

Hot Deals SAVE up to $100 per booking: Valid on new bookings made10/20 - 11/30/14 for travel through 12/17/15. Roundtrip airfare and minimum 3-night stay at a participating Hot Deals resort required. Discount is per booking, taken at time of booking and reflected in rates shown.

$200 Instant Air Credit Offer: Valid on new bookings made 9/15 - 12/31/14 for travel any time to Mexico, the Caribbean or Central America. Minimum 3-night hotel accommodations and roundtrip airfare required. Discount is per booking and taken at the time of booking. *Travel must originate from one of the following departure gateways only: Indianapolis (IND), Kansas City (MCI), Chicago (ORD), Des Moines (DSM), Detroit (DTW), Flint (FNT), Grand Rapids (GRR), Kalamazoo/Battle Creek (AZO), Lansing (LAN), Saginaw (MBS), Traverse City (TVC), Duluth (DLH), Minneapolis (MSP), Rochester (RST), Appleton (ATW), Eau Claire (EAU), Green Bay (GRB), La Crosse (LSE), Madison (MSN), Milwaukee (MKE), Wausau (CWA), Bismarck (BIS), Fargo (FAR), Grand Forks (GFK), Minot (MOT), Rapid City (RAP), Sioux Falls (FSD), Lincoln (LNK), Omaha (OMA), Cincinnati (CVG), Cleveland (CLE), Columbus (CMH) and Pittsburgh (PIT). Offer is subject to change or cancellation at any time at the sole discretion of Pleasant Holidays. Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]

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