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Caribbean

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Packages 1-100 of 1695
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Holiday Inn Sunspree Resort Montego Bay from $129.99+ (USD)

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Destination: Montego Bay
Region: Caribbean

The Mill Resort & Suites Aruba from $144.99+ (USD)

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Destination: Aruba
Region: Caribbean

Royal St. Kitts Hotel & Casino from $169.99+ (USD)

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Destination: St. Kitts
Region: Caribbean
Departure Cities: Boston, MA (BOS), New York City, NY (JFK), Newark, NJ (EWR)

Grotto Bay Beach Resort from $215.00+ (USD)

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Destination: Hamilton
Region: Caribbean
Departure Cities: Atlanta, GA (ATL), Boston, MA (BOS), Charlotte, NC (CLT), Chicago, IL (ORD), Dallas, TX (DFW), Denver, CO (DEN), Detroit, MI (DTW), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (JFK), Phoenix, AZ (PHX), Sacramento, CA (SMF), San Diego, CA (SAN), San Francisco, CA (SFO)
Description: Ocean View. Includes Kids 16 & younger stay FREE. More

Save 65% in Jamaica! from $239.00+ (USD)

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Destination: Negril
Region: Caribbean
Description: Save 65% @ Grand Pineapple Negril! More

45% Savings, All-Inclusive In Punta Cana! from $255.00+ (USD)

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Destination: Punta Cana
Region: Caribbean
Departure Cities: Albany, NY (ALB), Baltimore, MD (BWI), Boston, MA (BOS), Chicago, IL (ORD), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (NYC), Philadelphia, PA (PHL), Pittsburgh, PA (PIT), Syracuse, NY (SYR)
Description: Fun For Everyone @ Barcelo Punta Cana! More

Save 55% @ Holiday Inn SunSpree Aruba! from $259.00+ (USD)

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Destination: Aruba
Region: Caribbean
Departure Cities: Atlanta, GA (ATL), Baltimore, MD (BWI), Boston, MA (BOS), Chicago, IL (ORD), Hartford, CT (BDL), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (NYC), Philadelphia, PA (PHL)
Description: Save 55% @ Holiday Inn SunSpree Resort Aruba! More

EXCLUSIVE - Save Up to 75% on Aruba from $289.00+ (USD)

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Destination: Aruba
Region: Caribbean
Departure Cities: Boston, MA (BOS), Chicago, IL (ORD), Denver, CO (DEN), Detroit, MI (DTW), Hartford, CT (BDL), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), Nashville, TN (BNA), New York City, NY (NYC), Philadelphia, PA (PHL)
Description: Save Up to 75% @ Divi Village Golf and Beach Resort More

Save 70% + Kids Under 13 Stay, Play, Eat FREE from $340.00+ (USD)

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Destination: Montego Bay
Region: Caribbean
Departure Cities: Boston, MA (BOS), Chicago, IL (ORD), Denver, CO (DEN), Detroit, MI (DTW), Hartford, CT (BDL), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), Nashville, TN (BNA), New York City, NY (NYC), Philadelphia, PA (PHL)
Description: Enjoy 5 Nights @ Holiday Inn SunSpree Montego Bay More

Spend Four Balmy Nights in Puerto Plata from $349.00+ (USD)

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Destination: Puerto Plata
Region: Caribbean
Departure Cities: Albany, NY (ALB), Baltimore, MD (BWI), Boston, MA (BOS), Chicago, IL (ORD), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (NYC), Philadelphia, PA (PHL), Pittsburgh, PA (PIT), Syracuse, NY (SYR)
Description: All Inclusive Fun in Punta Cana More

Vacation Stimulus Package - 2 FREE Nights from $359.00+ (USD)

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Destination: St Thomas
Region: Caribbean
Description: Spend 4 Nights @ Wyndham Sugar Bay Resort and Spa More

Save 35% and Enjoy an Upgrade in Ocho Rios! from $365.00+ (USD)

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Destination: Ocho Rios
Region: Caribbean
Departure Cities: Albany, NY (ALB), Baltimore, MD (BWI), Boston, MA (BOS), Chicago, IL (ORD), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (NYC), Philadelphia, PA (PHL), Pittsburgh, PA (PIT), Syracuse, NY (SYR)
Description: All-Inclusive @ Sunset Jamaica Grande Resort & Spa! More

Save up to 25% in Punta Cana from $379.00+ (USD)

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Destination: Punta Cana
Region: Caribbean
Description: Save up to 25% in Punta Cana More

Oualie Beach Resort, Nevis from $379.99+ (USD)

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Destination: Nevis
Region: Caribbean

Sheraton Nassau Beach Resort from $385.00+ (USD)

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Destination: Cable Beach
Region: Caribbean
Departure Cities: Atlanta, GA (ATL), Boston, MA (BOS), Charlotte, NC (CLT), Chicago, IL (ORD), Dallas, TX (DFW), Denver, CO (DEN), Detroit, MI (DTW), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (JFK), Phoenix, AZ (PHX), Sacramento, CA (SMF), San Diego, CA (SAN), San Francisco, CA (SFO)
Description: Includes daily breakfast PLUS Kids 17 & younger stay FREE. More

Twice the Vacation FREE @ St. Kitts Marriott! from $389.00+ (USD)

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Destination: St. Kitts
Region: Caribbean
Departure Cities: Boston, MA (BOS), Chicago, IL (ORD), Hartford, CT (BDL), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), Nashville, TN (BNA), New York City, NY (NYC), Philadelphia, PA (PHL)
Description: Stay For 7 Nights, Pay For 4 @ St. Kitts Marriott! More

Save 65% In Aruba! from $399.00+ (USD)

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Occidental Grand Punta Cana from $438.00+ (USD)

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Destination: Punta Cana
Region: Caribbean
Departure Cities: Atlanta, GA (ATL), Boston, MA (BOS), Charlotte, NC (CLT), Chicago, IL (ORD), Dallas, TX (DFW), Denver, CO (DEN), Detroit, MI (DTW), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (JFK), Phoenix, AZ (PHX), Sacramento, CA (SMF), San Diego, CA (SAN), San Francisco, CA (SFO)
Description: All-Inclusive includes, all meals, drinks, activities and more! More

All-Inclusive, 4 Star Vacations In Punta Cana from $459.00+ (USD)

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Destination: Punta Cana
Region: Caribbean
Departure Cities: New York City, NY (JFK)
Description: All-Inclusive, 4 Star Vacations @ Occidental Grand More

Beaches Sandy Bay from $494.00+ (USD)

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Destination: Negril
Region: Caribbean
Departure Cities: Atlanta, GA (ATL), Boston, MA (BOS), Charlotte, NC (CLT), Chicago, IL (ORD), Dallas, TX (DFW), Denver, CO (DEN), Detroit, MI (DTW), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (JFK), Phoenix, AZ (PHX), Sacramento, CA (SMF), San Diego, CA (SAN), San Francisco, CA (SFO)
Description: Luxury Included« Family Vacation. More

Atlantis, Paradise Island Coral & Beach Towers from $501.00+ (USD)

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Destination: Paradise Island
Region: Caribbean
Departure Cities: Atlanta, GA (ATL), Boston, MA (BOS), Charlotte, NC (CLT), Chicago, IL (ORD), Dallas, TX (DFW), Denver, CO (DEN), Detroit, MI (DTW), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (JFK), Phoenix, AZ (PHX), Sacramento, CA (SMF), San Diego, CA (SAN), San Francisco, CA (SFO)
Description: Includes reduced rate PLUS Kids 11 & younger stay FREE. More

Riu Palace Paradise Island from $509.00+ (USD)

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Destination: Paradise Island
Region: Caribbean
Departure Cities: Atlanta, GA (ATL), Boston, MA (BOS), Charlotte, NC (CLT), Chicago, IL (ORD), Dallas, TX (DFW), Denver, CO (DEN), Detroit, MI (DTW), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (JFK), Phoenix, AZ (PHX), Sacramento, CA (SMF), San Diego, CA (SAN), San Francisco, CA (SFO)
Description: Ocean View Junior Suite. All-Inclusive includes, all meals, drinks, activities and more! More

Accra Beach Hotel & Resort from $515.00+ (USD)

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Destination: Barbados
Region: Caribbean
Departure Cities: Atlanta, GA (ATL), Boston, MA (BOS), Charlotte, NC (CLT), Chicago, IL (ORD), Dallas, TX (DFW), Denver, CO (DEN), Detroit, MI (DTW), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (JFK), Phoenix, AZ (PHX), Sacramento, CA (SMF), San Diego, CA (SAN), San Francisco, CA (SFO)
Description: Includes Kids 11 & younger stay FREE More

Leave Your Cares Behind @ Breezes Bahamas from $525.00+ (USD)

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Destination: Cable Beach
Region: Caribbean
Departure Cities: Atlanta, GA (ATL), Boston, MA (BOS), Chicago, IL (ORD), Denver, CO (DEN), Hartford, CT (BDL), Kansas City, MO (MCI), Los Angeles, CA (LAX), Miami, FL (MIA), New Orleans, LA (MSY), New York City, NY (NYC), Philadelphia, PA (PHL)
Description: Have a Super Vacation @ Breezes Bahamas More

Wyndham Rio Mar Beach Resort & Spa, A Wyndham Grand Resort from $533.00+ (USD)

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Destination: San Juan
Region: Caribbean
Departure Cities: Atlanta, GA (ATL), Boston, MA (BOS), Charlotte, NC (CLT), Chicago, IL (ORD), Dallas, TX (DFW), Denver, CO (DEN), Detroit, MI (DTW), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (JFK), Phoenix, AZ (PHX), Sacramento, CA (SMF), San Diego, CA (SAN), San Francisco, CA (SFO)
Description: Includes reduced rate, daily breakfast buffet PLUS Kids 18 & younger stay FREE. More

Wyndham Sugar Bay Resort & Spa from $538.00+ (USD)

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Destination: St Thomas
Region: Caribbean
Departure Cities: Atlanta, GA (ATL), Boston, MA (BOS), Charlotte, NC (CLT), Chicago, IL (ORD), Dallas, TX (DFW), Denver, CO (DEN), Detroit, MI (DTW), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (JFK), Phoenix, AZ (PHX), Sacramento, CA (SMF), San Diego, CA (SAN), San Francisco, CA (SFO)
Description: Includes 3rd & 4th night FREE, $100 food and beverage credit PLUS Kids 17 & younger stay FREE. (Must be booked by 11/30/09) More

Sunset Beach Resort and Spa from $551.00+ (USD)

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Destination: Montego Bay
Region: Caribbean
Departure Cities: Atlanta, GA (ATL), Boston, MA (BOS), Charlotte, NC (CLT), Chicago, IL (ORD), Dallas, TX (DFW), Denver, CO (DEN), Detroit, MI (DTW), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (JFK), Phoenix, AZ (PHX), Sacramento, CA (SMF), San Diego, CA (SAN), San Francisco, CA (SFO)
Description: All-Inclusive includes, all meals, drinks, activities and more! PLUS two Kids 15 & younger stay FREE. More

Beaches Boscobel Resort & Golf Club from $552.00+ (USD)

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Destination: Ocho Rios
Region: Caribbean
Departure Cities: Atlanta, GA (ATL), Boston, MA (BOS), Charlotte, NC (CLT), Chicago, IL (ORD), Dallas, TX (DFW), Denver, CO (DEN), Detroit, MI (DTW), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (JFK), Phoenix, AZ (PHX), Sacramento, CA (SMF), San Diego, CA (SAN), San Francisco, CA (SFO)
Description: Luxury Included« Family Vacation. More

Riu Negril Hotel from $552.00+ (USD)

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Amsterdam Manor Beach Resort Aruba from $556.00+ (USD)

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Destination: Reina Beatrix
Region: Caribbean
Departure Cities: Atlanta, GA (ATL), Boston, MA (BOS), Charlotte, NC (CLT), Chicago, IL (ORD), Dallas, TX (DFW), Denver, CO (DEN), Detroit, MI (DTW), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (JFK), Phoenix, AZ (PHX), Sacramento, CA (SMF), San Diego, CA (SAN), San Francisco, CA (SFO)
Description: Includes reduced rate. More

The Ritz-Carlton,San Juan Hotel, Spa & Casino from $556.00+ (USD)

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Renaissance Aruba Resort & Casino from $558.00+ (USD)

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Save 50% In Antigua @ St. James's Club! from $559.00+ (USD)

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Destination: Antigua
Region: Caribbean
Departure Cities: Albany, NY (ALB), Baltimore, MD (BWI), Boston, MA (BOS), Chicago, IL (ORD), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (NYC), Philadelphia, PA (PHL), Pittsburgh, PA (PIT), Syracuse, NY (SYR)
Description: Save 50%, All-Inclusive @ St. James's Club Antigua! More

Save 50% This Winter In Jamaica! from $559.00+ (USD)

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Destination: Montego Bay
Region: Caribbean
Departure Cities: Baltimore, MD (BWI), Boston, MA (BOS), Chicago, IL (ORD), Detroit, MI (DTW), Hartford, CT (BDL), Kansas City, MO (MCI), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (NYC), Philadelphia, PA (PHL), Pittsburgh, PA (PIT), Syracuse, NY (SYR)
Description: All-Inclusive Fun And Sun @ Sandals Inn! More

Two FREE Nights, Daily Breakfast in St Thomas from $569.00+ (USD)

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Destination: St Thomas
Region: Caribbean
Departure Cities: Boston, MA (BOS), Chicago, IL (ORD), Denver, CO (DEN), Detroit, MI (DTW), Hartford, CT (BDL), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), Nashville, TN (BNA), New York City, NY (NYC), Philadelphia, PA (PHL)
Description: 5th and 6th Night FREE @ Marriott Frenchman's Reef More

Sirenis Punta Cana Resort from $569.99+ (USD)

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Destination: Punta Cana
Region: Caribbean
Departure Cities: Baltimore, MD (BWI), Chicago, IL (ORD), Cleveland, OH (CLE), Detroit, MI (DTW), Philadelphia, PA (PHL), St Louis, MO (STL)

Sandals Negril Beach Resort & Spa from $585.00+ (USD)

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3rd Night Free @ Renaissance Marina Hotel! from $585.00+ (USD)

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Destination: Aruba
Region: Caribbean
Departure Cities: Baltimore, MD (BWI), Boston, MA (BOS), Chicago, IL (ORD), Denver, CO (DEN), Detroit, MI (DTW), Hartford, CT (BDL), Houston, TX (IAH), Kansas City, MO (MCI), Los Angeles, CA (LAX), Miami, FL (MIA), Nashville, TN (BNA), New Orleans, LA (MSY), New York City, NY (NYC), Philadelphia, PA (PHL)
Description: Breakfast for Two and Casino Credits @ Renaissance Marina Hotel More

Grand Cayman Beach Suites from $594.00+ (USD)

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Destination: Grand Cayman
Region: Caribbean
Departure Cities: Atlanta, GA (ATL), Boston, MA (BOS), Charlotte, NC (CLT), Chicago, IL (ORD), Dallas, TX (DFW), Denver, CO (DEN), Detroit, MI (DTW), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (JFK), Phoenix, AZ (PHX), Sacramento, CA (SMF), San Diego, CA (SAN), San Francisco, CA (SFO)
Description: Ocean View One-Bedroom Suite. Includes reduced rate. More

The Ritz Carlton, Golf & Spa Resort, Rose Hall from $597.00+ (USD)

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Destination: Rose Hall
Region: Caribbean
Departure Cities: Atlanta, GA (ATL), Boston, MA (BOS), Charlotte, NC (CLT), Chicago, IL (ORD), Dallas, TX (DFW), Denver, CO (DEN), Detroit, MI (DTW), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (JFK), Phoenix, AZ (PHX), Sacramento, CA (SMF), San Diego, CA (SAN), San Francisco, CA (SFO)
Description: Includes 4th night FREE PLUS Kids 17 & younger stay FREE. (Must be booked by 12/15/09) More

Shaw Park Beach Hotel & Spa from $599.99+ (USD)

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Destination: Ocho Rios
Region: Caribbean
Departure Cities: Chicago, IL (ORD), Detroit, MI (DTW), Milwaukee, WI (MKE), Minneapolis/St Paul, MN (MSP), St Louis, MO (STL)

Dreams Punta Cana Resort & Spa from $599.99+ (USD)

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Destination: Punta Cana
Region: Caribbean
Departure Cities: Baltimore, MD (BWI), Boston, MA (BOS), Chicago, IL (ORD), Cleveland, OH (CLE), Detroit, MI (DTW), Milwaukee, WI (MKE), Minneapolis/St Paul, MN (MSP), Philadelphia, PA (PHL), Pittsburgh, PA (PIT), St Louis, MO (STL)

Comfort Suites Cayman Islands from $614.99+ (USD)

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Destination: Grand Cayman
Region: Caribbean
Departure Cities: Chicago, IL (ORD), Dallas, TX (DFW), Detroit, MI (DTW), Houston, TX (IAH), Minneapolis/St Paul, MN (MSP), St Louis, MO (STL)

Save 35% in St. Martin from $615.00+ (USD)

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Destination: St. Maarten
Region: Caribbean
Description: Save 35% in St. Martin More

Grand Case Beach Club from $619.00+ (USD)

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Destination: St. Maarten
Region: Caribbean
Departure Cities: Atlanta, GA (ATL), Boston, MA (BOS), Charlotte, NC (CLT), Chicago, IL (ORD), Dallas, TX (DFW), Denver, CO (DEN), Detroit, MI (DTW), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (JFK), Phoenix, AZ (PHX), Sacramento, CA (SMF), San Diego, CA (SAN), San Francisco, CA (SFO)
Description: Includes welcome bottle of wine, daily Continental breakfast for ALL, non-motorized water sports and more! More

5th Night FREE @ Jade Mountain Anse Chastanet from $624.00+ (USD)

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Destination: St. Lucia
Region: Caribbean
Departure Cities: New York City, NY (JFK)
Description: 5th Night FREE @ Jade Mountain Anse Chastanet More

Sunshine Suites Resort from $624.99+ (USD)

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Destination: Grand Cayman
Region: Caribbean
Departure Cities: Chicago, IL (ORD), Dallas, TX (DFW), Detroit, MI (DTW), Houston, TX (IAH), Minneapolis/St Paul, MN (MSP)

Grand Palladium Bavaro Resort from $629.99+ (USD)

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Destination: Punta Cana
Region: Caribbean
Departure Cities: Baltimore, MD (BWI), Chicago, IL (ORD), Cincinnati, OH (CVG), Cleveland, OH (CLE), Detroit, MI (DTW), Milwaukee, WI (MKE), Philadelphia, PA (PHL), Pittsburgh, PA (PIT), St Louis, MO (STL)

The Fairmont Southampton from $634.99+ (USD)

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Destination: Bermuda
Region: Caribbean
Departure Cities: Boston, MA (BOS), New York City, NY (JFK), Newark, NJ (EWR), Philadelphia, PA (PHL)

Stay For 4 Nights, Pay for 2 in St. Thomas! from $645.00+ (USD)

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Destination: St Thomas
Region: Caribbean
Departure Cities: Atlanta, GA (ATL), Boston, MA (BOS), Chicago, IL (ORD), Detroit, MI (DTW), Houston, TX (IAH), Kansas City, MO (MCI), Las Vegas, NV (LAS), Los Angeles, CA (LAX), Miami, FL (MIA), New Orleans, LA (MSY), New York City, NY (NYC), Philadelphia, PA (PHL)
Description: Stay For 4 Nights, Pay for 2 PLUS More @Wyndham Sugar Bay Resort & Spa More

The Crane Resort & Residences from $646.00+ (USD)

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Iberostar Punta Cana Resort from $649.99+ (USD)

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Destination: Punta Cana
Region: Caribbean
Departure Cities: Baltimore, MD (BWI), Chicago, IL (ORD), Cleveland, OH (CLE), Detroit, MI (DTW), Milwaukee, WI (MKE), Minneapolis/St Paul, MN (MSP), Philadelphia, PA (PHL), Pittsburgh, PA (PIT), St Louis, MO (STL)

Melia Caribe Tropical from $653.00+ (USD)

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Destination: Punta Cana
Region: Caribbean
Departure Cities: Atlanta, GA (ATL), Boston, MA (BOS), Charlotte, NC (CLT), Chicago, IL (ORD), Dallas, TX (DFW), Denver, CO (DEN), Detroit, MI (DTW), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (JFK), Phoenix, AZ (PHX), Sacramento, CA (SMF), San Diego, CA (SAN), San Francisco, CA (SFO)
Description: Junior Suite. All-Inclusive includes, all meals, drinks, activities and more! More

Save 35% in St. Martin! from $659.00+ (USD)

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Destination: St. Maarten
Region: Caribbean
Description: Save 35% in St. Martin! More

Viva Wyndham Fortuna Beach from $669.99+ (USD)

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Destination: Freeport
Region: Caribbean
Departure Cities: Boston, MA (BOS), Chicago, IL (ORD), Dallas, TX (DFW), Houston, TX (IAH)

Hotel Samsara from $669.99+ (USD)

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Destination: Negril
Region: Caribbean
Departure Cities: Milwaukee, WI (MKE), St Louis, MO (STL)

Hilton Barbados from $670.00+ (USD)

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Sandals Grande Ocho Rios Beach & Villa Golf Resort from $678.00+ (USD)

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Riu Bambu from $689.99+ (USD)

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Destination: Punta Cana
Region: Caribbean
Departure Cities: Chicago, IL (ORD), Detroit, MI (DTW), Milwaukee, WI (MKE), Minneapolis/St Paul, MN (MSP), St Louis, MO (STL)

Beaches Negril Resort & Spa from $693.00+ (USD)

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Beaches Turks & Caicos Resort Villages & Spa from $696.00+ (USD)

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Destination: Providenciales
Region: Caribbean
Departure Cities: Atlanta, GA (ATL), Boston, MA (BOS), Charlotte, NC (CLT), Chicago, IL (ORD), Dallas, TX (DFW), Denver, CO (DEN), Detroit, MI (DTW), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (JFK), Phoenix, AZ (PHX), Sacramento, CA (SMF), San Diego, CA (SAN), San Francisco, CA (SFO)
Description: Luxury Included« Family Vacation. More

The Fairmont Hamilton Princess from $699.99+ (USD)

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Destination: Bermuda
Region: Caribbean
Departure Cities: Boston, MA (BOS), New York City, NY (JFK), Newark, NJ (EWR), Philadelphia, PA (PHL)

Melia Caribe Tropical from $699.99+ (USD)

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Destination: Punta Cana
Region: Caribbean
Departure Cities: Milwaukee, WI (MKE), St Louis, MO (STL)

Grand Palladium Jamaica & Lady Hamilton from $699.99+ (USD)

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Destination: Montego Bay
Region: Caribbean
Departure Cities: Baltimore, MD (BWI), Chicago, IL (ORD), Detroit, MI (DTW), Milwaukee, WI (MKE), Minneapolis/St Paul, MN (MSP), St Louis, MO (STL)

Riu Montego Bay from $699.99+ (USD)

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Sandals Royal Bahamian Spa Resort & Offshore Island from $701.00+ (USD)

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Destination: Cable Beach
Region: Caribbean
Departure Cities: Atlanta, GA (ATL), Boston, MA (BOS), Charlotte, NC (CLT), Chicago, IL (ORD), Dallas, TX (DFW), Denver, CO (DEN), Detroit, MI (DTW), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (JFK), Phoenix, AZ (PHX), Sacramento, CA (SMF), San Diego, CA (SAN), San Francisco, CA (SFO)
Description: Luxury Included« Vacation includes anytime snacks at beachside grills, all meals and fine dining options; unlimited premium brand drinks; luxurious ac... More

Bahia Principe Punta Cana from $719.99+ (USD)

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Destination: Punta Cana
Region: Caribbean
Departure Cities: Baltimore, MD (BWI), Boston, MA (BOS), Chicago, IL (ORD), Cincinnati, OH (CVG), Cleveland, OH (CLE), Detroit, MI (DTW), Milwaukee, WI (MKE), Minneapolis/St Paul, MN (MSP), Philadelphia, PA (PHL), Pittsburgh, PA (PIT), St Louis, MO (STL)

The Alexandra from $720.00+ (USD)

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The Ritz-Carlton, Grand Cayman from $727.00+ (USD)

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Destination: Grand Cayman
Region: Caribbean
Departure Cities: Atlanta, GA (ATL), Boston, MA (BOS), Charlotte, NC (CLT), Chicago, IL (ORD), Dallas, TX (DFW), Denver, CO (DEN), Detroit, MI (DTW), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (JFK), Phoenix, AZ (PHX), Sacramento, CA (SMF), San Diego, CA (SAN), San Francisco, CA (SFO)
Description: Includes reduced rate PLUS Kids 17 & younger stay FREE! More

Occidental Grand Punta Cana from $739.99+ (USD)

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Destination: Punta Cana
Region: Caribbean
Departure Cities: Chicago, IL (ORD)

Nh Real Arena from $739.99+ (USD)

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Destination: Punta Cana
Region: Caribbean
Departure Cities: Baltimore, MD (BWI), Chicago, IL (ORD), Cleveland, OH (CLE), Philadelphia, PA (PHL)

Save 50% In Jamaica! from $749.00+ (USD)

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Destination: Ocho Rios
Region: Caribbean
Departure Cities: Baltimore, MD (BWI), Boston, MA (BOS), Chicago, IL (ORD), Detroit, MI (DTW), Hartford, CT (BDL), Kansas City, MO (MCI), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (NYC), Philadelphia, PA (PHL), Pittsburgh, PA (PIT), Syracuse, NY (SYR)
Description: Save 50% And Relax In Luxury @ Sandals Dunn's River! More

Iberostar Rose Hall Beach Hote from $749.99+ (USD)

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Sandals Dunn's River Villaggio Golf Resort & Spa from $760.00+ (USD)

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Sandals Montego Bay from $762.00+ (USD)

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Destination: Montego Bay
Region: Caribbean
Departure Cities: Atlanta, GA (ATL), Boston, MA (BOS), Charlotte, NC (CLT), Chicago, IL (ORD), Dallas, TX (DFW), Denver, CO (DEN), Detroit, MI (DTW), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (JFK), Phoenix, AZ (PHX), Sacramento, CA (SMF), San Diego, CA (SAN), San Francisco, CA (SFO)
Description: Luxury Included« Vacation includes anytime snacks at beachside grills, all meals and fine dining options; unlimited premium brand drinks; luxurious ac... More

50% Savings @ Grand Pineapple Beach Antigua from $765.00+ (USD)

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Destination: Antigua
Region: Caribbean
Description: Spend 4 Nights in Antigua @ Grand Pineapple Beach Antigua More

Dreams Palm Beach Punta Cana from $766.00+ (USD)

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Destination: Punta Cana
Region: Caribbean
Departure Cities: Atlanta, GA (ATL), Boston, MA (BOS), Charlotte, NC (CLT), Chicago, IL (ORD), Dallas, TX (DFW), Denver, CO (DEN), Detroit, MI (DTW), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (JFK), Phoenix, AZ (PHX), Sacramento, CA (SMF), San Diego, CA (SAN), San Francisco, CA (SFO)
Description: Unlimited-Luxury« All-Inclusive includes all meals, drinks, activities and more! More

Ocean Blue Golf & Beach Resort from $779.99+ (USD)

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Destination: Punta Cana
Region: Caribbean
Departure Cities: Boston, MA (BOS), Chicago, IL (ORD), Detroit, MI (DTW)

Every 4th & 7th Night Free in Anguilla! from $785.00+ (USD)

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Destination: Anguilla
Region: Caribbean
Description: Every 4th & 7th Night Free in Anguilla! More

Riu Palace Punta Cana from $789.99+ (USD)

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Destination: Punta Cana
Region: Caribbean
Departure Cities: Baltimore, MD (BWI), Chicago, IL (ORD), Detroit, MI (DTW), Minneapolis/St Paul, MN (MSP), Philadelphia, PA (PHL), Pittsburgh, PA (PIT), St Louis, MO (STL)

Sandals Halcyon Beach St. Lucia from $792.00+ (USD)

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Destination: St. Lucia
Region: Caribbean
Departure Cities: Atlanta, GA (ATL), Boston, MA (BOS), Charlotte, NC (CLT), Chicago, IL (ORD), Dallas, TX (DFW), Denver, CO (DEN), Detroit, MI (DTW), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (JFK), Phoenix, AZ (PHX), Sacramento, CA (SMF), San Diego, CA (SAN), San Francisco, CA (SFO)
Description: Luxury Included« Vacation includes anytime snacks at beachside grills, all meals and fine dining options; unlimited premium brand drinks; luxurious ac... More

A Lush Tropical Paradise for 55% Less from $795.00+ (USD)

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Destination: St. Lucia
Region: Caribbean
Departure Cities: Baltimore, MD (BWI), Boston, MA (BOS), Chicago, IL (ORD), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (JFK), New York City, NY (NYC), Philadelphia, PA (PHL), Pittsburgh, PA (PIT), Syracuse, NY (SYR)
Description: Relax for 4 Nights @ Sandals Regency La Toc Golf Resort & Spa More

Iberostar Bavaro Beach Resort from $799.99+ (USD)

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Destination: Punta Cana
Region: Caribbean
Departure Cities: Chicago, IL (ORD), Detroit, MI (DTW)

Gran Bahia Principe La Romana from $799.99+ (USD)

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Destination: La Romana
Region: Caribbean
Departure Cities: Baltimore, MD (BWI), Boston, MA (BOS), Cincinnati, OH (CVG), Cleveland, OH (CLE), Philadelphia, PA (PHL), Pittsburgh, PA (PIT)

Iberostar Dominicana Resort from $809.99+ (USD)

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Destination: Punta Cana
Region: Caribbean
Departure Cities: Chicago, IL (ORD)

Bavaro Princess Hotel from $809.99+ (USD)

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Destination: Punta Cana
Region: Caribbean
Departure Cities: Baltimore, MD (BWI), Boston, MA (BOS), Chicago, IL (ORD), Cleveland, OH (CLE), Detroit, MI (DTW), Philadelphia, PA (PHL), Pittsburgh, PA (PIT)

Sandals Royal Caribbean Resort & Private Island from $813.00+ (USD)

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Destination: Montego Bay
Region: Caribbean
Departure Cities: Atlanta, GA (ATL), Boston, MA (BOS), Charlotte, NC (CLT), Chicago, IL (ORD), Dallas, TX (DFW), Denver, CO (DEN), Detroit, MI (DTW), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (JFK), Phoenix, AZ (PHX), Sacramento, CA (SMF), San Diego, CA (SAN), San Francisco, CA (SFO)
Description: Luxury Included« Vacation includes anytime snacks at beachside grills, all meals and fine dining options; unlimited premium brand drinks; luxurious ac... More

Visit Unique, Historic Curacao - Save 25% from $815.00+ (USD)

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Destination: Curacao
Region: Caribbean
Departure Cities: Baltimore, MD (BWI), Boston, MA (BOS), Chicago, IL (ORD), Miami, FL (MIA), New York City, NY (NYC), Philadelphia, PA (PHL)
Description: Relax for 4 Nights @ Curacao Marriott Resort & Emerald Casino More

Dreams La Romana Resort & Spa from $819.00+ (USD)

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Destination: La Romana
Region: Caribbean
Departure Cities: Baltimore, MD (BWI), Boston, MA (BOS), Chicago, IL (ORD), Cleveland, OH (CLE), Philadelphia, PA (PHL), Pittsburgh, PA (PIT), Washington D.C. (IAD)

Point Village from $819.99+ (USD)

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Destination: Negril
Region: Caribbean
Departure Cities: St Louis, MO (STL)

Grand Oasis Punta Cana from $819.99+ (USD)

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Destination: Punta Cana
Region: Caribbean
Departure Cities: Baltimore, MD (BWI), Boston, MA (BOS), Chicago, IL (ORD), Cincinnati, OH (CVG), Pittsburgh, PA (PIT)

Sandals Regency La Toc Golf Resort & Spa in St. Lucia from $825.00+ (USD)

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Sun Value Save 40% All Inclusive in St Thomas from $829.00+ (USD)

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Destination: St Thomas
Region: Caribbean
Description: Spend 4 Nights in St Thomas @ Wyndham Sugar Bay Resort and Spa More

Grand Pineapple Beach Antigua from $835.00+ (USD)

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Destination: Antigua
Region: Caribbean
Departure Cities: Atlanta, GA (ATL), Boston, MA (BOS), Charlotte, NC (CLT), Chicago, IL (ORD), Dallas, TX (DFW), Denver, CO (DEN), Detroit, MI (DTW), Houston, TX (IAH), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (JFK), Phoenix, AZ (PHX), Sacramento, CA (SMF), San Diego, CA (SAN), San Francisco, CA (SFO)
Description: All-Inclusive includes, all meals, drinks activities and more! More

**5th Night FREE @ Ritz-Carlton Rose Hall** from $845.00+ (USD)

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Destination: Montego Bay
Region: Caribbean
Departure Cities: Albany, NY (ALB), Baltimore, MD (BWI), Boston, MA (BOS), Chicago, IL (ORD), Los Angeles, CA (LAX), Miami, FL (MIA), New York City, NY (NYC), Philadelphia, PA (PHL), Pittsburgh, PA (PIT), Syracuse, NY (SYR)
Description: Five Star Luxury @ Ritz-Carlton Golf & Spa Resort Rose Hall More

Ifa Bavaro Village from $849.99+ (USD)

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Destination: Punta Cana
Region: Caribbean
Departure Cities: Boston, MA (BOS), Chicago, IL (ORD)

Dreams Palm Beach from $869.99+ (USD)

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Destination: Punta Cana
Region: Caribbean
Departure Cities: Baltimore, MD (BWI), Boston, MA (BOS), Chicago, IL (ORD), Cleveland, OH (CLE), Philadelphia, PA (PHL), Pittsburgh, PA (PIT)

New, Classic All Inclusive Plan on Aruba! from $875.00+ (USD)

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Destination: Aruba
Region: Caribbean
Description: Enjoy The Westin Resort, Aruba's New All Inclusive Plan More

Riu Montego Bay from $879.99+ (USD)

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Destination: Montego Bay
Region: Caribbean
Departure Cities: Buffalo, NY (BUF)

Golden Bear Lodge from $879.99+ (USD)

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Destination: Punta Cana
Region: Caribbean
Departure Cities: Baltimore, MD (BWI), Cleveland, OH (CLE), Philadelphia, PA (PHL), Pittsburgh, PA (PIT)

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Gran Bahia Principe Ambar from $1,179.99+ (USD)

The Royal West Indies Resort

Esmeralda Resort

Gran Bahia Principe La Romana from $799.99+ (USD)

Gr Oasis Marien Bch Rst & Spa from $1,539.99+ (USD)

Plus sign (+) means taxes and fees are additional