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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

    Dominican Republic, Punta Cana

    Secrets Cap Cana Resort & Spa - Unlimited-Luxury®

    Sixth night free + $200 in resort coupon

    Plus, free upgrade, free night certificate for return stay when book six nights or more and earn 7,500 Rapid Rewards points per member or save $300 per vacation package. Book a flight + hotel vacation package of $500 or more, and save $300 when use the promo code 300OCT20 at the time of booking. Three-night minimum stay required. Resort coupons are issued for select amenities including spa treatments, romantic dining experiences, and wine purchases. Blackout dates apply: 12/23/20 - 12/31/20; 2/11/21 - 2/15/21; 3/27/21 - 4/3/21. Book by 10/26/20 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

    Dominican Republic, Punta Cana

    Riu Palace Bavaro - All Inclusive

    Save up to 68% + complimentary room upgrade

    Plus, earn 7,500 Rapid Rewards points per member or save $300 per vacation package. Book a flight + hotel vacation package of $500 or more, and save $300 when use the promo code 300OCT20 at the time of booking. Free guaranteed room upgrade from Jr Suite Gardenview to Jr Suite Superior. Three-night minimum stay required. Book by 10/26/20 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

    Secrets Wild Orchid Montego Bay - Unlimited-Luxury®

    Sixth night free + $200 in resort coupon

    Plus, free upgrade and free night certificate for return stay when book six nights or more and earn 7,500 Rapid Rewards points per member or save $300 per vacation package. Book a flight + hotel vacation package of $500 or more, and save $300 when use the promo code 300OCT20 at the time of booking. 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. Three-night minimum stay required. Blackout dates apply: 12/23/20 - 12/31/20; 2/11/21 - 2/15/21; 3/27/21 - 4/3/21. Book by 10/26/20 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
    View departure dates