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Caribbean Vacation Packages from $479

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$200 Instant Air Credit
Valid from select Midwest gateways*
Book by 12/31/14 for travel anytime
Pleasant Caribbean Holidays

3 nights from $695


3 nights from $589

Dominican Republic

3 nights from $765

More Great Deals

Puerto Rico

3 nights from $479


3 nights from $669

Turks & Caicos

3 nights from $1,279


3 nights from $919

Grand Cayman

3 nights from $1,035


3 nights from $965

St. Kitts and Nevis

3 nights from $895

St. Martin

3 nights from $989

St. Lucia

4 nights from $1,265

Rates are based on roundtrip air travel to/from Atlanta (ATL) departures to Aruba, Orlando (MCO) departures to Puerto Rico, Bahamas, Dominica, Jamaica and St. Martin/Maartin, Chicago (ORD) departures to Bermuda, Dominican Republic and St. Kitts & Nevis, New York (JFK) departures to Cayman Islands and Turks & Caicos and Boston (BOS) departures to St. Lucia, for select travel 3/5/15 for Bermuda, 5/18/15 for Dominica, 4/23/15 for Turks & Caicos, 5/11/15 for Jamaica and 5/4/15 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.

$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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