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Caribbean vacations

Southwest Vacations® offers spectacular vacation deals to the Caribbean. With a variety of exciting destinations and amazing accommodations, you can create an ideal tropical all-inclusive vacation package.

Featured deals to the Caribbean

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  • All-inclusive

    Jamaica, Montego Bay

    Secrets Wild Orchid Montego Bay - Unlimited-Luxury®

    Save $100 + save up to 45%

    Plus, $200 in resort coupons and free upgrade. Book a flight + hotel package of $1,500 or more, and save $100 when use the promo code MAYINTHAW at the time of booking. Hotel savings vary depending on date of travel. Three-night minimum stay required. Resort coupons are issued per room, per stay. Resort coupons are issued for limited discounts on select amenities including spa treatments, a romantic dining experience, and wine purchases. Book by 6/1/20 by 6:00 p.m. CT. Like this deal, but want more flexibility? Look for the Search More Options link to change your length of stay.

    5 nights hotel + flight from
    $ 0 total per person
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  • All-inclusive

    Jamaica, Montego Bay

    Ocean Coral Spring

    Save $100 + save up to 60%

    Plus, first child free. Book a flight + hotel package of $1,500 or more, and save $100 when you use the promo code MAYINTHAW at the time of booking. Three-night minimum stay required. First child free valid for travel 6/7/20-6/19/20 and 9/1/20-10/29/20. Book by 6/1/20 by 6:00 p.m. CT. Like this deal, but want more flexibility? Look for the Search More Options link to change your length of stay.

    5 nights hotel + flight from
    $ 0 total per person
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  • All-inclusive

    Jamaica, Montego Bay

    Iberostar Rose Hall Beach - AI

    Save $100 + save up to 45%

    Plus, up to $500 in resort credits. Book a flight + hotel vacation package of $1,500 or more to IBEROSTAR Hotels & Resorts, and save $100 when you use the promo code MAYINTHAW at the time of booking. Hotel savings vary depending on date of travel. Three-night minimum stay required. Stay three to five nights and get $300 in resort coupons. Or, stay six nights or more and get $500 in resort coupons. Book by 6/1/20 by 6:00 p.m. CT. Like this deal, but want more flexibility? Look for the Search More Options link to change your length of stay.

    4 nights hotel + flight from
    $ 0 total per person
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