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Caribbean vacation packages.

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.

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Featured deals to the Caribbean

Featured deals to the Caribbean

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  • TripAdvisor traveler rating
    based on TripAdvisor reviews
    Save up to 40%
    25% discount on spa services + free in-room breakfast + $200 in resort coupons
    Breathless Montego Bay Resort & Spa - All Inclusive
    5 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive

    Jamaica, Montego Bay

    Best priced departure dates
    May 20, 2024
    5 nights hotel + flight from
    $2,382 per person
  • TripAdvisor traveler rating
    based on TripAdvisor reviews
    Savings up to $300
    Riu Palace Tropical Bay - All Inclusive
    5 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive

    Jamaica, Montego Bay

    Best priced departure dates
    May 5, 2024
    5 nights hotel + flight from
    $1,207 per person
  • TripAdvisor traveler rating
    based on TripAdvisor reviews
    Savings up to $300
    Royalton Blue Waters Montego Bay, An Autograph Collection - All Inclusive
    5 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive

    Jamaica, Montego Bay

    Best priced departure dates
    May 5, 2024
    5 nights hotel + flight from
    $1,599 per person
  • Save up to 40%
    $200 in resort coupons + free in-room breakfast + 25% spa discount
    Dreams Flora Resort & Spa - All Inclusive
    5 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive

    Dominican Republic, Punta Cana

    Best priced departure dates
    May 11, 2024
    5 nights hotel + flight from
    $1,394 per person
  • TripAdvisor traveler rating
    based on TripAdvisor reviews
    Save up to 25%
    Resort credits up to $800 + free private roundtrip transfers
    Iberostar Grand Bavaro - All-Inclusive
    5 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive

    Dominican Republic, Punta Cana

    Best priced departure dates
    Jul 22, 2024
    5 nights hotel + flight from
    $1,869 per person
  • Hard Rock Hotel and Casino Punta Cana - All-Inclusive
    5 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive

    Dominican Republic, Punta Cana

    Best priced departure dates
    May 11, 2024
    5 nights hotel + flight from
    $1,919 per person
  • TripAdvisor traveler rating
    based on TripAdvisor reviews
    Save up to 40%
    25% discount on spa services + free in-room breakfast + $200 in resort coupons
    Secrets St. James Montego Bay - All Inclusive
    5 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive

    Jamaica, Montego Bay

    Best priced departure dates
    May 18, 2024
    5 nights hotel + flight from
    $1,576 per person
  • TripAdvisor traveler rating
    based on TripAdvisor reviews
    Iberostar Grand Rose Hall - All Inclusive
    5 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive

    Jamaica, Montego Bay

    Best priced departure dates
    May 11, 2024
    5 nights hotel + flight from
    $1,838 per person
  • TripAdvisor traveler rating
    based on TripAdvisor reviews
    Grand Palladium Jamaica Resort and Spa - All Inclusive
    4 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive

    Jamaica, Montego Bay

    Best priced departure dates
    May 11, 2024
    5 nights hotel + flight from
    $1,298 per person
  • Royalton Negril, An Autograph Collection - All Inclusive
    5 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive

    Jamaica, Montego Bay

    Best priced departure dates
    May 18, 2024
    5 nights hotel + flight from
    $1,527 per person
  • TripAdvisor traveler rating
    based on TripAdvisor reviews
    Save up to 40%
    25% discount on spa services + free in-room breakfast + $200 in resort coupons
    Secrets Wild Orchid Montego Bay - All Inclusive
    5 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive

    Jamaica, Montego Bay

    Best priced departure dates
    Jul 8, 2024
    5 nights hotel + flight from
    $1,731 per person
  • TripAdvisor traveler rating
    based on TripAdvisor reviews
    Riu Palace Jamaica - All Inclusive
    5 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive

    Jamaica, Montego Bay

    Best priced departure dates
    May 11, 2024
    5 nights hotel + flight from
    $1,639 per person
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†First and second checked bags. Weight and size limits apply. A golf bag can be substituted for one checked bag.

Seats are limited and may not be available on some flights that operate during peak travel times and holiday periods. Flight and hotel rates may vary by day of week. Hotel surcharges may apply to weekends, holidays, and convention periods. Flights available on published, scheduled service only. Rates may be subject to change until purchased. Discounts are valid per reservation before taxes are applied. Offer not valid on existing reservations and may not be combined with any other offer. Subject to availability. Restrictions apply. ALG Vacations Corp. is the tour operator for Southwest Vacations®.