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    Regent Seven Seas Cruises®

    $5999—Luxury Caribbean cruise on all-suite ship in winter

    $5999 Luxury Caribbean cruise on all-suite ship in winter

    Cayman Islands, Jamaica, Belize and Mexico
    Set sail on Seven Seas Mariner® and explore the shores of the Cayman Islands, Jamaica, Mexico and more.
    Dec. 10
  • $599—Weeklong Caribbean cruise w/$285 credit
    Sign in to unlock our member-exclusive rates

    TOP 20 - Sells out quickly! $599 Weeklong Caribbean cruise w/$285 credit

    Half Moon Cay, Grand Turk, San Juan, St. Thomas, Ocho Rios, Amber Cove, Nassau, Bimini
    Visit Jamaica, the Bahamas, the U.S. Virgin Islands and more on a warm weather retreat this winter.
    November-December; surrounding dates on sale
    TOP 20 - Sells out quickly!
  • Book now at

    AutoRentals.com

    $30 & up—Montego Bay, Jamaica car rentals

    $30 & up Montego Bay, Jamaica car rentals

    Jamaica
    Book now to lock in the best pricing. The lowest prices are for 'pay now' options; pay a little more to cancel anytime.
    Through 2025
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    Holland America Line

    $649 & up—7-night Western Caribbean cruise incl. taxes

    $649 & up 7-night Western Caribbean cruise incl. taxes

    Half Moon Cay, Ocho Rios, Georgetown, Cozumel
    On this roundtrip sail from Miami, you'll hop between four tropical destinations.
    November 2025
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    All Inclusive Outlet

    $709 & up—Montego Bay: 4 nights at new RIU with flights

    $709 & up Montego Bay: 4 nights at new RIU with flights

    Jamaica
    Located on White Bay Beach, RIU Palace Aquarelle is an upscale all-inclusive resort catering to couples and families.
    August; other dates also available
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    All Inclusive Outlet

    $799 & up—Adults-only Jamaica 4-night trip with flights

    $799 & up Adults-only Jamaica 4-night trip with flights

    Runaway Bay
    Soak up the Caribbean sun on the private beach or by one of three pools at Bahia Principe Luxury Runaway Bay.
    August; other dates also on sale
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    All Inclusive Outlet

    $759 & up—Upscale Jamaica all-inclusive trip with air

    $759 & up Upscale Jamaica all-inclusive trip with air

    Montego Bay
    Enjoy sun and sand at the 4-star Grand Palladium Lady Hamilton Resort & Spa, home to five pools and 17 bars for ultimate vacation vibes.
    August; more dates on sale
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    Visit Jamaica

    Up to 35% off—Jamaica all-inclusive hotel + flight packages

    Up to 35% off Jamaica all-inclusive hotel + flight packages

    Visit Jamaica • Montego Bay, Negril, Ocho Rios
    Get ready to experience the rhythm of Jamaica with this sale on all-inclusive travel packages.
    into 2026
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    Oceania Cruises

    $3840—Upscale 12-night Caribbean cruise

    $3840 Upscale 12-night Caribbean cruise

    Belize, Jamaica, Cayman Islands and more
    Stay in an upgraded cabin on a warm-weather escape this winter. A $1200 spending credit per cabin is included.
    January 2026
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    All Inclusive Outlet

    $789 & up—Montego Bay: all-ages resort + flights

    $789 & up Montego Bay: all-ages resort + flights

    Jamaica
    Give your next family vacation some Jamaican flair with a trip to Iberostar Waves Rose Hall Beach. Relax on a white sand beach or pool side.
    September; other dates also on sale
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    All Inclusive Outlet

    $779 & up—Jamaica oasis: 4-night Negril trip w/air & more

    $779 & up Jamaica oasis: 4-night Negril trip w/air & more

    Negril
    Slip away to the upscale Azul Beach Resort Negril, set on the world-famous 7 Mile Beach, with access to 24-hour room service, water sports and more.
    September; other dates also available
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